At the beginning of the year I was going through letterboxd and realized I had seen just a bit over 50% of history's best picture winners. Being someone who loves the Oscars I thought that was pretty weak, so I set out to watch every past winner I hadn't seen before this year's ceremony. With Oppenheimer winning last night and bringing this awards season to a close, I'm finally ready to put this out there, my ranking of every best picture winner in the history of the Academy Awards. These picks are all based on my personal opinion, so some stuff you like may not wind up as high as you'd like but that's okay! With every entry I will also say whether I believe the film should have won based on the other nominees. So without further adieu... here is my ranking of EVERY best picture winner.
#96 The Broadway Melody (1929) - In one of my film theory classes we had to read about a critic who claimed the advent of sound would be the death of cinema, and I can see where he was coming from now. This draws a tough line from a filmmaking standpoint as it is one of the earliest "talkies," but the way the film just drops a camera in front of people and lets scenes play out does not work. This gives long pauses between lines and shots that sit still for several seconds until someone starts talking. Now, I could look past the flaws in editing and chalk them up to flaws of the times, but I won't because this is also just a gross movie. Half of the runtime is men doing and saying uncomfortable things to women making it just icky to watch, and most of the other half is just said women shouting. There truly isn't a likeable character and the musical numbers are not good or common enough to make waiting for them worthwhile. It garners historical importance as the first "talkie" to win best picture and supposedly the first musical, but if the trade off for sound is rampant misogyny and brutal editing I'd rather the Academy have awarded a silent film. It's a shame to dunk on something so old, but this is the worst best picture winner. Should it have won: No. Anything else.
#95 Gigi (1958) - Being a best picture winner, I did have some expectations for this. Those expectations were crushed, this is a movie I could barely get through. It's very colourful which is fun, but that vibrant look does nothing to stop how dull the movie is. It's bland and honestly pretty annoying with music and characters that did absolutely nothing for me. One of the absolute worst winners without question. Should it have won: Obviously not, haven't seen the other nominees but they can't be worse than this.
#94 Cavalcade (1933) - Apparently this was Hitler's favourite movie so on the surface that's reason enough to be skeptical about it. But if you were worried about enjoying the favourite movie of such a horrid person, do not fret cause I can't see many people liking these two hours of pure banality. On top of lacking even a drop of energy, this isn't shot well, it has poor direction, and most of the actors are overacting a ton yet somehow being dull. Aside from trying to see every best picture winner there isn't really any reason to watch this. Should it have won: I don't even care who the other nominees were I'm saying no.
#93 Cimarron (1931) - Don't have much to say about this one. Another early winner than aged like milk, it's intensely uninteresting, it's a bit racist, and it just drags on for two hours. Aside from trying to complete the best picture gauntlet there's no reason to watch this. Should it have won: There had to have been something else.
#92 Crash (2005) - This isn't the worst movie I've ever seen but it really isn't good at all. I tried to go in open minded but Paul Haggis' passion project has more in common with a cheap soap opera than a best picture thanks largely in part to egregious overacting and frankly goofy musical choices throughout. The basic ideas he's approaching are agreeable but he tackles race relations in a very cartoonishly surface level way that causes it all to fall flat. Some moments work but too many feel completely tone deaf, and the cinematography is the only thing I'd say is good throughout the movie. Should it have won: This beating Brokeback Mountain is a travesty.
#91 Tom Jones (1963) - I don't even know what to say about this one. It feels like a parody of Shakespeare but I genuinely can't tell if it's supposed to. It's certainly watchable but also feels so much longer than it is and there aren't many points that are actually all that entertaining. I did like the opening, but other than that this was quite a miss. Should it have won: I think not.
#90 The Greatest Show on Earth (1952) - For a film called The Greatest Show on Earth it definitely isn't. There are some highlights, the iconic train crash is great and James Stewart as a clown is pretty awesome. Aside from that though, this is a long attempt at an epic that ultimately falls flat for most of its runtime. Despite centering around the circus there is so little fun and joy, sucking the life out of something that could be full of energy and gorgeous sets and costumes. Just ultimately a big let down. Should it have won: I highly doubt it.
#89 Around the World in Eighty Days (1956) - This is a movie I wish I could have put higher. It opens really strong, with David Niven giving a fun energetic performance in a very entertaining build up to the titular adventure around the world. Similarly, the ending wraps things up with a fun charming tone that I really enjoyed. Everything in between is where it lost me. There are good moments sprinkled throughout but much of the middle part of the movie drags, and rather than use the story to showcase different cultures around the world in a fun way, we get a few different places brought to life through pretty stereotyped and cartoonish depictions. It's a perfectly watchable movie but its missteps really bring it down. Should it have won: Probably not.
#88 Out of Africa (1985) - Sincerest apologies to her royal majesty one Meryl Streep, but this was not my cup of tea. Admittedly it is a great looking movie, with some really strong cinematography captured gorgeous settings. Performance wise this is quite good too, with Streep and Robert Redford putting in some great work. The film just really never finds its footing to me, it starts out solid enough but kind of just drags from there, and with a near three hour runtime that dragging gets tedious at a point. I hate to use the word "boring" with regards to movies but sadly this one just kind of is. Should it have won: No, give it to The Color Purple.
#87 The Great Ziegfeld (1936) - This is tough because I fully understand why it won. It's very grand and filled with elaborate set pieces and musical numbers that just flaunt wealth and extravagance which I can easily see people in 1936 gawking over. Looking at it from a contemporary point of view it mostly just feels overindulgent and overlong, ultimately losing the steam gained from it's beautiful moments, but I can appreciate why people would love it back in the day. Should it have won: While I wouldn't call it a good movie this is a win that I understand.
#86 Titanic (1997) - Full disclosure, it has been ages since I saw Titanic. That being said I can only go off of what I remember and I remember being underwhelmed. Yes there is a ton of good with it but also a ton of cheese that I've struggled to look past. Maybe I'll like it more on a rewatch, maybe I won't, maybe he would have fit on that door. Should it have won: I'd have gone with Good Will Hunting but I know people love this so it's fine.
#85 How Green Was My Valley (1941) - I really wish I could put this higher but I just didn't enjoy it. It's a pretty terrific looking film but I've found I struggle getting into John Ford movies and despite it's great visuals that was the case here. It's pretty well acted I just never found myself caring about the characters enough and was pretty consistently zoning out. I'll probably give it another shot some day and maybe it'll move up the list. Should it have won: This beat Citizen Kane. No.
#84 The Artist (2011) - The Artist is a beautiful movie. Great production design, great costumes, stunning black and white cinematography. Sadly for a film holding this much glitz and glamour I find it sorely lacking in energy. I wish I loved it, and it feels right up my alley, but the strong visual style just doesn't fully make up for what I find it lacking tonally and narratively. Singin in the Rain covers similar ground but does so far better and over 50 years earlier. Should it have won: no, there are so many other options like Moneyball, Hugo, The Help, and The Descendants that would have made much better winners.
#83 Shakespeare in Love (1998) - This is a movie that has grown on me over time. I watched it in school and absolutely hated it, I thought it was just boring. But as my appreciation for film and literature has grown I have gotten to a point where I like the movie now. That being said, I still don't love it and it holds a fair deal of faults that make me question it as a best picture winner. A good, but not a great movie. Should it have won: I'm not even the biggest Saving Private Ryan fan but come on, what are we doin here.
#82 Driving Miss Daisy (1989) - This is a perfectly fine movie. It's charming, it has good music, it has a very solid Morgan Freeman performance, and it looks decent. Narratively though it just leaves a lot to be desired. It's a very surface level movie that pats itself on the back for doing the bare minimum, and in a year where Spike Lee's groundbreaking Do the Right Thing came out this just fails to shine. Should it have won: Do the Right Thing not even being nominated is absolute buffoonery but even looking just at what DID get nominated, this was not the right choice.
#81 The English Patient (1996) - I really wanted to like this more than I did. I still appreciated a lot of this, it's a film where basically every department is putting in good work, I just found the sum of these great parts a bit underwhelming. It's a beautiful film with a sweeping feel to it that I really appreciated, with great sets and settings captured by great cinematography. Musically I enjoyed the film, and the performances especially from Ralph Fiennes were pretty strong. I just didn't find the film itself all that interesting, and I found myself just coasting along with it rather than becoming truly invested in the story. Should it have won: I can see why it would win but Fargo should have.
#80 Gandhi (1982) - This actually didn't feel as long as I expected it to being an over 3 hour historical epic. That being said, I still wasn't necessarily wowed. It's a good movie, it has a terrific Ben Kingsley performance, and it tells the story of a very important historical figure, but the filmmaking never becomes anything better than solid. The production design, the cinematography, everything is basically just operating at a good enough level to make it worthwhile but never special. Should it have won: No chance, give it to E.T..
#79 The Life of Emile Zola (1937) - This is a pretty solid movie. It tells a rather interesting story made even more compelling by the politics of the time as it follows the trial of a wrongly convicted Jewish soldier right when anti-Semitism was growing. The film itself does get a bit dull at points but has some exciting moments and pretty strong acting throughout. Not a ton to say about this one, just a solid movie. Should it have won: I haven't seen the other nominees so sure.
#78 Dances with Wolves (1990) - I should preface that this is very much not my thing, a three hour movie taking place mostly in plains is not my cup of tea. I did find myself a fan though, largely thanks to the representation for Native Americans the film gives. It's cinematography also makes the most out of what I find relatively uninteresting landscapes so I have to applaud it for that. The movie has some lulls though, and I don't think Kevin Costner is all that good in it in front of the camera. Should it have won: Similarly to Shakespeare in Love, this just had nothing on one of the other nominees so this should have been Goodfellas.
#77 Chariots of Fire (1981) - This is another movie that's just fine. Despite how famous that opening song is I actually found it to be some of the worst music in this as the score is honestly pretty great. It's also a solid looking movie, I just really struggled to connect with the narrative. Just a perfectly serviceable movie but nothing special. Should it have won: Over Raiders of the Lost Ark? Absolutely not.
#76 A Man for All Seasons (1966) - I wanted to love this but it didn't fully work for me. Paul Scofield's lead performance is really strong, and when the plot picks up it's pretty damn interesting leading up to a great ending. It just takes too much time to get into said plot, starting off good but taking forever to get to it and in turn leaving me a bit uninterested for a while. A lot of good but overall didn't wow me. Should it have won: Haven't seen the other nominees but I've heard better things about Who's Afraid of Virginia Woolf?
#75 The Last Emperor (1987) - This is one I started out really enjoying but lost interest as it went along. The film tells the life story of China's last emperor, covering decades over its runtime. This is by no means a bad thing, but while I connected a lot with his early years I just didn't care as much as it went along. There's an extravagance to the sets and costumes, and really the story itself that I enjoyed spending time with, but I just wasn't left feeling much by the end. Should it have won: I haven't seen anything else so I guess I'm okay with this one.
#74 Slumdog Millionaire (2008) - This is where I start to like the movies a decent bit. With Danny Boyle behind the camera there's a lot to enjoy about the filmmaking on hand, and his ability to operate with a project that has so much of another language spoken is impressive. All the present day stuff I enjoyed a lot, it's just the flashbacks that I found lacking a bit and caused it to lose a lot of steam. Should it have won: I've only seen one of the other nominees, but that one is The Curious Case of Benjamin Button which I think would be far more deserving.
#73 Green Book (2018) - This movie takes so much hate. Yes on the surface it's just a swapped Driving Miss Daisy, and there are some things about the production that leave cause for concern, the movie itself though is harmless and honestly pretty good. I love Mahershala Ali in this, earning a well deserved second Oscar, and Viggo Mortensen is great too. If it didn't win the big award I don't think people would have much of a problem with this one, it's a solid watch. Should it have won: As much as this is a fine movie, Roma would have been my choice and BlackKKlansman would have been a great winner.
#72 From Here to Eternity (1953) - I wasn't necessarily wowed by this but it's pretty solid. Set in Hawaii during WWII it gives a unique look into the war, but also does so by focusing squarely on the people rather than combat. The performances are really great, and while I wasn't hooked from start to finish the ending is pretty great. Should it have won: Haven't seen the other nominees so I'm okay with it.
#71 Going My Way (1944) - This is just a perfectly enjoyable movie. It doesn't necessarily do anything special but Bing Crosby is very endearing in the lead role and brings not only a great performance but some great singing as well. I like the look of the film, the story is a nice ride, and while it does run on a bit too long it ends on a good note. Nothing spectacular but a nice watch. Should it have won: Over Double Indemnity and Gaslight this is a pretty meh choice.
#70 Gentleman's Agreement (1947) - This is a pretty interesting watch. Coming out just after World War 2 it has a unique approach to the still relevant topic of anti-Semitism. When the film is focused on that it is very effective, especially in way the child of Gregory Peck's character faces it, but when the film deviates from that it loses some steam. It's still a really good movie though, and Gregory Peck is pretty fantastic. Should it have won: I'd have gone with Miracle on 34th Street but this is a decent pick.
#69 Grand Hotel (1932) - This is a really solid early ensemble drama. We're put in the Grand Hotel and follow a handful of characters each facing different turmoil, and it's fairly effective. The narrative isn't overly gripping but the performances are all really good, making you care for the characters whether or not you care about their story. There are certainly points where its age catches up to it and the pacing drags, but overall it's a strong effort and has some sneaky great cinematography. Should it have won: Sure I have no problem with it.
#68 A Beautiful Mind (2001) - This is a very of its time movie. It boasts a strong lead performance from Russell Crowe and solid supporting roles around him. The story is pretty enjoyable and delivers a strong emotional journey while the script does a good job of building up to the film's twist. Ultimately this just doesn't leave that much of an impact on you, it's good but it feels tonally similar to so many early 2000s movies that it doesn't really give you too much to chew on. Still solid though. Should it have won: The best movie nominated would be Fellowship of the Ring but with the trilogy taking the gold later I'm okay with this, would have probably preferred Moulin Rouge though.
#67 Annie Hall (1977) - To get the elephant out of the room right away: Woody Allen sucks. That being said this is pretty good. It's pretty fun and both Allen and Diane Keaton are incredibly charming in front of the camera with some great chemistry. It's a solid looking movie too, though it doesn't have that "Best Picture" feel too it largely due to a short runtime that is filled with quite a bit of repetition. Should it have won: What do you talk about more: Annie Hall, or Star Wars? I rest my case.
#66 Hamlet (1948) - This is just a solid adaptation of Hamlet. There are certainly better versions but there's no denying that Laurence Olivier kills this in the titular role. It's well acted, it looks good, I don't have much else to say honestly, just a solid adaptation. Should it have won: I don't hate that it won but my pick would be The Red Shoes.
#65 The Best Years of Our Lives (1946) - This is a very Oscar friendly movie. It boasts great acting, strong writing, and it's a fairly visually enticing work. Coming just a few years after WWII it is also very much of the times. That being said, while I do appreciate it, the runtime I don't really find justified based on what the film ultimately delivers. It's still good but it certainly drags a bit. Should it have won: While I do like this movie and it feels very Academy friendly, it has nothing on It's a Wonderful Life.
#64 Oliver! (1968) - This is one of the most British movies I've ever seen. This Charles Dickens adaptation isn't necessarily anything groundbreaking or overly special, but it's quite good. I really liked the set and costumes, and the musical numbers especially after the intermission are quite great. Narratively I wasn't overly wowed, but there's enough good here to make it worthwhile. Should it have won: Sure!
#63 My Fair Lady (1964) - This is basically a musical about how much snooty rich dudes can suck and for that it's quite fun. Audrey Hepburn is terrific, navigating this misogynistic society with a fun performance going from a flower girl to a member of high society and nailing that transition. The costumes and sets are fantastic throughout, and while the film runs a bit too long I still enjoyed. Should it have won: I don't think so, Dr. Strangelove or Mary Poppins would have been better choices.
#62 Mrs. Miniver (1942) - This is an imperfect film with some incredible moments. From a performance standpoint there's nothing to complain about, and Wyler does a great job here showing the horrors of war from a non-soldier point of view. The cinematography and sound design work hand in hand really well to craft some devastating moments, a lot of the film just struggles to fully reach that same level of emotional impact. Should it have won: This is a good movie and I haven't seen the other nominees so I have no problem with this.
#61 An American in Paris (1951) - Looking at Vincente Minelli's career this is certainly not his best but certainly eons better than Gigi. Gene Kelly is magnetic as always, delivering a ton of charm and of course some amazing dancing. Like Gigi this is a very colourful film but the gorgeous sets and costumes are aiding a much more worthwhile story here. Should it have won: I would have gone with A Streetcar Named Desire but this is still a solid choice.
#60 No Country for Old Men (2007) - This is a movie I definitely need to rewatch. When I first saw it I enjoyed it but I was ultimately a bit underwhelmed and I haven't revisited it since. That being said, there is a ton to appreciate, whether that be great direction from the Coens or an astonishingly great performance by Javier Bardem. I'm not huge on Westerns so that could be where some of my hesitation comes from, but maybe if I watch it again one day it'll move up on the list. Should it have won: I'm sure a lot of people would say yes but I think There Will Be Blood and Juno would have been better picks.
#59 Marty (1955) - This operates in a similar vein to Annie Hall, a short and sweet romantic comedy that in no way feels like an Oscar movie. Marty (both the movie and the character) is extremely charming, and the film gives us a bunch of very endearing performances headlined by Ernest Borgnine. The story is really entertaining, although it doesn't leave much to chew on after the fact. It's a strange film in the best picture pantheon but one I'm honestly really glad is there. Should it have won: Sure why not.
#58 Terms of Endearment (1983) - This is one that didn't quite hit how I wanted to but I still appreciate a good deal. The performances here are all really fantastic, especially the dynamic at the heart of it between Shirley MacLaine and Debra Winger. The script is great, doing a terrific job of showing the complicated mother daughter dynamic between the two. The biggest thing holding me back with this one is just how melodramatic it can feel, and a lot of that is thanks to some kind of overbearing music that I wish was toned down. Still, this is an emotionally rich and very well acted movie. Should it have won: No problem with this win.
#57 Nomadland (2020) - It's kind of crazy that this was basically a runaway best picture winner. Not that I don't like it, I enjoy it quite a bit, but a film this subtle and small in scale making waves the way it did is kind of crazy. This is a pretty gorgeous film, with Chloe Zhao and cinematographer Joshua James Richards really making the most of their surroundings. Frances McDormand wasn't win worthy in my opinion but is still really good in the lead, and the music is quite strong. It's a beautiful and thematically rich movie that I enjoyed much more than I had anticipated thanks to those strengths. Should it have won: As much as I do like Nomadland it's actually my least favourite of the nominees from this year, I'm okay with the win but I genuinely would have gone with anything else.
#56 The King's Speech (2010) - Winning best picture is somehow the worst thing that could have happened for this film's legacy. I really like it. It's a gorgeous period piece and tells a great story I knew nothing about before watching. Colin Firth is at his near best here, and both Geoffrey Rush and Helena Bonham Carter are incredible in supporting roles. If David Fincher had an Oscar right now I don't think people would look back at this with disdain the way so many do. Should it have won: As I said before I think winning over The Social Network is one of the worst things going for this, solid movie but nothing on Fincher's classic.
#55 Wings (1927) - The first best picture winner ever. This is tough to place, as it isn't the easiest watch being a near 100 year old silent film clocking in at nearly two and a half hours. That being said, this is insanely impressive. There's one tracking shot that you can find on Youtube pretty easily that honestly rivals the best shots I've seen, and that's only the half of it. There are so many flying scenes that are captured incredibly well, and plane crashes that look better than stuff we'd see today. The story isn't necessarily wowing, but from a technical standpoint this is a marvel even today, and the fact that this was possible a near century ago is kind of crazy. Should it have won: This is interesting as there was another award similar to best picture which Sunrise won, so in a way we kind of got two best picture winners and both are very deserving.
#54 All the King's Men (1949) - Actually surprised myself with how much I enjoyed this. It has a fascinating story of a good man becoming corrupt as he gains power that hooked me from beginning to end. Willie starts out such a genuinely endearing man only to become borderline evil in his persona and Broderick Crawford nails that character arc. It's cut together really well too, and the cinematography kind of echoes the darkness that comes over the character. This film feels way ahead of its time in how it tackles a political arc like this and I really enjoyed it. Should it have won: Yes big time.
#53 CODA (2021) - It's hard not to love CODA. The little engine that could of the 2021/2022 awards race, this is a movie that often looked like it would end up missing out on a nomination and wound up winning the whole thing. It doesn't match the prestige of other winners but despite the negative sentiment some throw its way this is still a really well crafted film by Sian Heder. It's really well written and has a good enough visual style to carry the strong script. I love the cast, and while it does get very sentimental I don't think that's a bad thing. This road to winning the gold was just such a joy and I really enjoy the movie too. Should it have won: I wish it was Dune or Licorice Pizza but this was a very fun win, even if it isn't the most deserving one.
#52 Mutiny on the Bounty (1935) - One of the best early winners. Clarke Gable is terrific as the leading man in one of the better boat movies I've ever seen. We follow him as he leads a revolt on the HMS Bounty being run by a delightfully evil Charles Laughton. The tensions between all the characters on the boat are really exciting despite the film's age, and whether it be the scenes on land or at sea I really loved the look of this. The at sea scenes are pretty impressively done too it's really cool to see an older movie capture them so well. This is definitely what one might consider a "dad movie" nowadays, but this is a really cool one. Should it have won: Sadly no cause I love Top Hat.
#51 Ben-Hur (1959) - Let me start by saying the iconic chariot scene is one of the best scenes of all time. I genuinely couldn't believe some of the things caught on film as chariots are crashing into each other and people are being run over by horses, it's crazy. Outside of that scene, this is a good movie that I just couldn't quite call great. Charlton Heston is good and the main story is pretty interesting, but I don't think it earns its very long runtime. I'm not anti-long movies but there are many many points that just lose energy and left me uninterested. When it's epic, it is capital E EPIC, but when it isn't it drags itself down from being something I love. Should it have won: Nope, this was up against arguably the second best courtroom drama of all time in Anatomy of a Murder which should win despite not having a chariot scene.
#50 Gone with the Wind (1939) - Gone with the Wind is such a tough film to place. Honestly, I liked it far more than I expected after years of it and its four hour runtime sitting in my watchlist taunting me. I actually really loved the first half, it has a huge scale to it and delivers some cinematography that still holds up as legendary today. I was pretty hooked early on too, with the two lead performances as well as Hattie McDaniels all working really well for me. Post-intermission I find it loses a lot of steam and just isn't nearly as interesting as the first half, but it ends on a very high note saving it from falling further down these rankings. Should it have won: I feel like Wizard of Oz should be the winner but I also understand with this film's grand stature.
#49 All Quiet on the Western Front (1930) - It's kinda crazy how well this film holds up. The third best picture winner and it really stands out as one of the few early winners that is looked back on fondly. The more character driven moments of this one didn't always hook me, likely due to how old it is, but there's so much else to appreciate. The war scenes are truly magnificent, bringing a sense of scale and realism I would never expect from something from this time. It has a killer ending and filmmaking that still holds up today. Should it have won: It was 1930 and this is a great war movie I'm gonna let it have the win.
#48 Patton (1970) - While All Quiet on the Western Front is a war movie that struggled a bit with character moments, this is one that is almost opposite to that. George C. Scott is THE reason to watch this, carrying a three hour film with one of the most commanding performances I've seen. The opening scene is iconic for a reason, and while the film has its lulls it remains one of the great war films offering a rare character study within the genre. The combat scenes are also pretty great. Should it have won: I haven't seen the other nominees so I'm more than okay with this.
#47 Argo (2012) - The only people I've seen not like this movie are Canadians. Yes the story minimizes Canada's part in the story, but that doesn't change how great of a movie it is. The blend of war movie and movie about filmmaking is really interesting and that's really what makes this such an interesting true story to me. It's tense and exciting thanks to Ben Affleck's direction, and his work in front of the camera is equally as strong. I love John Goodman and Alan Arkin in this as well, such a thrilling watch with terrific performances. Should it have won: There are better movies nominated, Django Unchained for example, but this is a solid winner.
#46 Lawrence of Arabia (1962) - This is the kind of masterpiece that ultimately just isn't for me. I appreciate the craft here a ton, this is a grand sweeping epic with incredible cinematography, set design, costume design, direction, acting, you name it. It is a masterpiece, and one that I do like, I just can't get as passionate about it as so many others. Most of that is due to the very lengthy runtime, part of that is the very patient storytelling for something of this length, regardless I do enjoy it still and I'd honestly love to revisit it and see if I enjoy it more. Should it have won: It may not fully be my thing but it's an iconic movie, no problem at all with this win.
#45 In the Heat of the Night (1967) - I would put this among the coolest best picture wins out there. Not only is Sidney Poitier the star just a few years after becoming the first black best actor winner, but it's a tense crime film from a decade where the other winners were musicals and long period epics. Great filmmaking from Jewison and of course an incredible Poitier performance in the lead. It's topical, it's well made, and I think it really stands out on its own among the winners of the 60s. Should it have won: Yeah! Great movie and I appreciate the icon Sidney Poitier getting praise.
#44 Birdman or (The Unexpected Virtue of Ignorance) (2014) - What a strange movie. An exciting return to relevance for Michael Keaton in a wildly meta and fascinating story. The craft here is spectacular with some of the best cinematography from the 2010s, and Keaton's great leading role is complemented by awesome supporting turns from Emma Stone and Edward Norton. Great movie that I really need to revisit. Should it have won: I really like this one, but over Whiplash, The Grand Budapest Hotel, and Boyhood, I just can't say it would be my winner.
#43 The Hurt Locker (2009) - With Kathryn Bigelow taking home the Oscar for best director this is a landmark film, marking the first female director winner. Making things even more interesting is that this is a film that has a lot to say about masculinity within the military. Despite some fun moments this is an extremely tense watch that has a kind of heartbreaking side to it with how tied to the war Jeremy Renner's character becomes. The performances are great, and there's some really savvy filmmaking, the opening scene in particular being one that I find very impressive. Bigelow is one of the best and this is one of her top works. Should it have won: This was a great crop of nominees and this is a decent winner, but I would give Inglorious Basterds the win over this.
#42 Million Dollar Baby (2004) - In the subgenre of "Clint Eastwood is a grumpy old guy" this is certainly the best. I'm always a sucker for boxing movies so this was right up my alley, but Hilary Swank's performance is what really won me over, delivering an endearing authenticity that is hard not to fall in love with. Eastwood is also pretty good, as is Morgan Freeman. The boxing scenes are pretty great, and it isn't often we get female boxing movies so that's something different which I enjoy, but the fight scenes have nothing on the film's emotional moments which really propel it to something great. Should it have won: Yeah I think this is a solid winner.
#41 Rain Man (1988) - Tom Cruise starts out as such a piece of shit in this but that makes his arc over the course of the film so rewarding. While Dustin Hoffman's performance wouldn't work today, I think the film is coming at the topic from a positive place so while it maybe hasn't aged well it isn't malicious by any means. This is an extremely touching story of family and how one person can help you grow as a person and I just found it extremely endearing. I'm a sucker for a good road trip movie and when you throw in these two great performances and a bunch of baseball references, it becomes a pretty easy sell for me. Should it have won: I think so, this is a great movie.
#40 Platoon (1986) - This is a pretty brutal war movie. While it isn't the best Vietnam War flick, not even the best to win Best Picture, this is one of the better combat based war films I've seen. Oliver Stone really shows how brutal it was, and the last line from Charlie Sheen showcases the lasting impact it had on those who fought. The film is shot very well, and the ensemble cast is awesome. Supporting turns from so many notable names including the likes of Willem Dafoe, Keith David, and Tony Todd won me over early and Stone's take on the war kept me impressed. Should it have won: no complaints here.
#39 You Can't Take It with You (1938) - With the combo of Frank Capra behind the camera and James Stewart in front of it I should have known this would be a hit. While it doesn't live up to what they'd later do with It's a Wonderful Life, this is still a delight of a film. Narratively it delivers a story that we've now seen countless renditions of, but with how early this is I won't hold that against it. Stewart and Jean Arthur have great chemistry in the leading roles, and another It's a Wonderful Life actor Lionel Barrymore gives a really lovely supporting performance. This is fun and witty, and despite losing a bit of steam in the third act I really really enjoyed it. Should it have won: Absolutely.
#38 The Sound of Music (1965) - I put off watching this for a very long time as it looked like frolicking in a field for three hours and that is not my jam. I was super wrong, this is a fantastic movie. It loses some steam in the tail end of the second act, but it's a beautiful sweeping musical epic with standout performances from Julie Andrews and Christopher Plummer. The war plot in the background gives this a ton of interesting depth to what is already a great movie. Ashamed it took me so long to watch this as I really enjoyed it a ton. Should it have won: I have no problem with this one, a big win for an iconic movie.
#37 Braveheart (1995) - This is a great time. It is riddled with cheese and campiness, and from what I've heard a good deal of historical inaccuracy, but those somehow make the whole thing so entertaining. It feels so epic despite its weaker points and has some genuinely strong emotional beats. Musically there's a great blend between James Horner's beautiful score and more traditional Scottish music creating a soundscape that is both inspiring and quite dynamic. The battles are awesome and despite an inflated runtime this is overall pretty damn exciting. Should it have won: Yes, it has flaws but is still a great movie.
#36 Spotlight (2015) - It's been a while since I last saw Spotlight, but there's no denying its impact. A tight and thrilling journalist thriller shedding light on a subject I knew very little about at time time that very much needed to be discussed more. The performances all around are incredible, and the cast is brining to life one of the strongest screenplays of the decade. I'd love to see Tom McCarthy tackle something like this again cause he really knocked this out of the park. Should it have won: It's a close call but I would have preferred The Revenant or The Martian.
#35 West Side Story (1961) - How can you not love West Side Story? While its story does take from other works, this tale essentially uses Romeo & Juliet to critique race related tensions in New York. This thematically rich tale is filled with incredible music and elaborate dance numbers, and set design that truly turns NYC into a stage. The performances are fantastic and it put Rita Moreno on the map which is a huge win. Should it have won: I haven't seen the other nominees and this is one of the all time great musicals so I'd say it deserves the win.
#34 The Bridge on the River Kwai (1957) - Not all war epics hit with me but this is one that I really enjoy. It truly feels epic from start to finish and somehow never drags despite ultimately being about a bridge. The iconic collapsing scene is truly a marvel to behold, and Alec Guinness gives a really great performance showing the moral back and forth he feels surrounding it's destruction. A truly great film. Should it have won: In an average year yes, but this was up against 12 Angry Men which is one of the all time greats so I can't say this should have won.
#33 Unforgiven (1992) - I am generally not a big fan of the Western genre, but when a good one comes around I can be seduced and this is definitely one of the good ones. Clint Eastwood leads what is a fairly standard story, but one elevated by some terrific filmmaking. Eastwood himself is actually pretty tender for the most part in this, and the camaraderie he has with Morgan Freeman is one of the highlights of the film. That being said, when he needs to get intense he can strike some real fear, even to a great Gene Hackman Villain. Like Eastwood's performance, the film operates with a good balance of compassionate moments with some of really broody atmosphere. Overall, a pretty damn great movie. Should it have won: Yeah I'd say so.
#32 Forrest Gump (1994) - Forrest Gump seems to be less and less beloved as the years go on. I would agree that some of it hasn't aged incredibly well, but this is still a pretty great movie. Tom Hanks is terrific carrying this story spanning so many moments in time. It's a story of one man but feels grand thanks to how many different walks of life Forrest finds himself in. There's so much rich emotion packed in here, all while also being quite fun. The effects are also really damn good for the time and the kind of movie this is. Should it have won: Over Pulp Fiction and The Shawshank Redemption? No.
#31 Kramer vs Kramer (1979) - This is an interesting movie to me because the actually Kramer v Kramer part of it really isn't what wowed me. I was expecting the courtroom part of it to be what won me over but so much of the film focuses on the relationship between Dustin Hoffman's Ted and his son. Having sole responsibility of his son for a while gives the character so much passion while fighting for custody that really struck a chord with me. Meryl Streep isn't in this a ton but there's a rawness to her performance coming before she fully became the icon that she is. It isn't what one expects from the title really, but this is a really intimately emotional film that I love. Should it have won: Going up against Apocalypse Now and All that Jazz makes this tough, I think any of the three would be a worthy winner though.
#30 Amadeus (1984) - Amadeus features one of the most interesting framing devices I've seen, telling the story of one of history's most iconic artists through a flashback told by a crazed rival. I didn't even realize until I watched it that F. Murray Abraham wasn't even playing Mozart, but boy does he marvel as the jealous and intense Salieri. Tom Hulce gives such a goofy performance as Mozart but in the context of the story it really works especially in contrast to Abraham's performance. The conducting scenes only help to give this story a grand feel, and the ending is superb. Should it have won: I hate to say it but I haven't even heard of the other nominees, so giving this iconic movie the win seems like the right call.
#29 Midnight Cowboy (1969) - This may be the most emotionally raw best picture winner. It isn't flashy nor is it based on a tragic tale we all know, it's just a story of two men trying to make their way in New York City despite some rough circumstances. Jon Voight brings such a hopeful charisma to the lead role that only makes the sad moments even harder. Dustin Hoffman is also incredible as someone who honestly starts out pretty sleazy only for you to fall for him just as hard as you fall for Voight. There are some truly chilling sequences and an ending that just punches you in the gut. Should it have won: I love Butch Cassidy & the Sundance Kid but I'd still pick this.
#28 Ordinary People (1980) - This is one that kind of floored me. As the title suggests it really is a movie about some pretty normal people who have their lives and relationships forever changed by a tragedy. This is filled with such rich emotional largely from the disconnect between Timothy Hutton's Conrad and his mother Beth played by Mary Tyler Moore. Donald Sutherland plays the father/husband in possibly my favourite role from his incredible career, bringing all the hope he can to the situation and then absolutely devastating when he realizes things might not be okay. He also acts as mediator between Conrad and Beth, with several moments of the two needing to reflect on their relationship in a crushing way with Sutherland trying his best to make them see the good in each other. The script here is amazing, really making you connect with all three characters in a deep way, making everything they say cut even harder. This is simply one of the most emotionally rich films I've seen so it makes sense I guess that it comes in right beside Midnight Cowboy. Should it have won: There's certainly an argument for Raging Bull but I'd take this one.
#27 The Godfather Part II (1974) - This is a film I'm sure will move up the list when I eventually rewatch it. As of now I've only seen it once and there's just too much to get a hold of after only one watch. That being said, it's pretty masterful. Following up its predecessor (which is still coming on this list), Francis Ford Coppola creates something even grander. Every piece of filmmaking from the sets to the cinematography to the costumes to the sound is damn near perfect, and Al Pacino's mastery of his role of Michael is almost matched by De Niro's introduction as a younger Vito Corleone. This is a true spectacular work. Should it have won: Yes, while I prefer the first film this is still incredible.
#26 It Happened One Night (1934) - From the first decade of best picture winners this is the clear best. While others of its time have aged like milk, this remains an absolute delight ninety years later. The chemistry between Clark Gable and Claudette Colbert is some of the best I've honestly ever seen, each of them delivering great work to turn an already fun script into something truly special. Its tone almost feels modern in how light and somewhat cheeky it is, making it one of the most entertaining watches of any best picture winner. Should it have won: Not only is this a great movie, but it's awesome that a romantic comedy this old is a best picture winner. A big yes from me.
#25 American Beauty (1999) - I wish a certain actor's reputation didn't affect how I feel about this movie, I used to absolutely love it, but I still think it's quite great. It's a pretty fascinating character study of someone allowing the mundanity of life to send them spiraling into self destruction. Real life aside, Kevin Spacey is pretty spectacular here in what may be his best work, and Annette Bening is near her best opposite him. There are also some really beautiful sequences sprinkled throughout this. Should it have won: 1999 was an incredible year for movies, but a lot of the top dogs are missing from these nominations so I'm okay with this given the other nominees.
#24 On the Waterfront (1954) - This is one hell of a film. Just a brilliantly put together drama packed with rich emotion. Marlon Brando is one of the all time greats, and I would argue quite firmly that this is his finest work, giving a performance that is both powerful and vulnerable. The writing is also fantastic, and the film looks honestly incredible. Love this movie. Should it have won: Yes, this is a near masterpiece and possibly Brando's best work.
#23 The Sting (1973) - I'm always a sucker for a good con/heist movie and this is one of the best. This is a kind of movie we haven't seen much of at the Oscars which makes its win even more fun. Paul Newman and Robert Redford are a ton of fun leading the film, and Robert Shaw delivers a great antagonist performance against them. The 1930s setting allows for some terrific set and costume design, as well as an old timey feel that I think added to the fun of it all. It's tense in a really satisfying way and I absolutely loved the ending. Great great movie. Should it have won: I have no problem with this but my choice would without question be The Exorcist.
#22 Rocky (1976) - How can you not love Rocky? Stallone delivers his best in the ultimate underdog story. As I mentioned before, I love boxing movies, and Rocky is the one that started that love. It's a film with so much heart, not only in the boxing storyline but even more so with the relationship between Rocky and Adrian. It's super cheesy, but it's the kind of uplifting cheesy that feels like it will always pass the test of time. Iconic. Should it have won: Taxi Driver should have won but it's also Rocky so I'm not complaining.
#21 12 Years a Slave (2013) - Steve McQueen is one of the great filmmakers of our time, and this may just be his greatest achievement. He brings his contemporary style to tell a mid-1800s story in a way that feels fresh while also delicately handling the very tough subject matter. It's a film that shows rather than preaches, depicting truly horrific things and never shying away from the truth of them. It's an expertly crafted film with standout performance from Chiwetel Ejiofor and Lupita Nyong'o as well as a strong villainous turn from Michael Fassbender. By no means an easy watch but a film I think everyone should see at some point. Should it have won: Her is my favourite of the nominees but this is a more important movie so I'm all for the win.
#20 The French Connection (1971) - This is such a great movie. This came just two years before Friedkin delivered one of the best horror films of all time in The Exorcist, and interestingly a lot of the creepy cinematography and music style from that can be seen here. Only in this case it's to craft a tense and thriller cat & mouse style crime movie. The iconic car chase is insane, but other moments like the subway scene make the film in its entirety an exciting ride. Gene Hackman and Roy Scheider are terrific and Fernando Rey is a perfect suave but unsettling villain in his limited screen time. Should it have won: it's close between this and A Clockwork Orange but between the two I would probably actually go with this one.
#19 Chicago (2002) - Chicago is awesome. Crazy to think that it's been over two decades since a musical took home best picture but this stands as one of the all time greats in my opinion. Lavish sets and electric editing help bring to life a soundtrack of fantastic musical numbers, including a show stopping finale that I absolutely adore. This is a case where perfect casting leads to terrific performances around the board, in turn leading to a great time. If you like glitz and glamour amidst a pretty edgy story this is an easy recommendation. Should it have won: Some iconic movies in the bunch, but I love this movie so I'm happy with it winning.
#18 Schindler's List (1993) - There's really not much more to say about this one. It should honestly probably be higher, but this is one movie I'm not eager to revisit despite how incredible it is. Spielberg delivers what I'd consider the definitive WWII film, one that focuses not on combat itself but of the horrors faced at the hands of the Nazis and one man's desperate quest to save as many as he could. It's one of the most visually perfect films ever made with it's stunning but also visceral use of colour, and Liam Neeson gives maybe one of the best performances of all time. It's a crushing movie but one everyone needs to see at least once. Should it have won: This is one movie I can't see anyone arguing against.
#17 All About Eve (1951) - This is one of those movies that feels grand without dripping in excess. Bette Davis and Anne Baxter highlight a pure showcase of powerhouse acting. A brilliant script from Joseph L. Mankiewicz is brought to life by a terrific ensemble, delivering a film that plays with the entertainment industry in an interesting way that almost feels like a chess match at times. The ending is one of the all time greats, building off over two hours of cleverness that I was hooked by. Should it have won: This is an interesting one as I feel like it and Sunset Boulevard are similar in screaming "Best Picture" but I would lean ever so slightly towards Sunset Boulevard.
#16 Gladiator (2000) - Gladiator is just awesome. Ridley Scott's epic just looks and feels expensive but in the best way. Elaborate sets and costumes help bring to life a gripping revenge story that flies by despite a pretty long runtime. Russell Crowe is almost too cool, and Joaquin Phoenix is perfectly weaselly. The combat is incredible but even when people aren't swinging swords at each other this is one of the most epic films of its time. Should it have won: 100% this is an icon.
#15 The Lost Weekend (1946) - Despite being a pretty big Billy Wilder fan, this is one that shocked me. Coming just two years after Double Indemnity, this continues his trend of blending witty dialogue with some pretty serious subject matter. The tone here gets quite dark, starting out kind of haunting before switching to a more pleasant romantic bit only to wind up shifting into a near horror movie. The last ten minutes or so are crushing in a somehow satisfying way with Jane Wyman acting her heart out as her character essentially tries to will things into being okay. Ray Milland is incredible, nailing Wilder's energetic dialogue but also hitting hard in the more somber moments. The cinematography is really clever, looking good throughout but with some shots that really add to that haunting atmosphere the film creates. This is a film I hadn't even heard of before trying to watch every winner, and here it is among my favourites. Should it have won: Absolutely, this is such an interesting best picture winner and an incredible movie.
#14 Rebecca (1940) - I'm a pretty big Alfred Hitchcock fan, but on the surface this doesn't look like it would be one of his more exciting works. Despite seemingly like an aristocratic romance, Rebecca is one of the most fascinating mystery films I've ever seen. In typical Hitchcock fashion the film is filled with exciting twists and turns, made eerie thanks to some fantastic gothic atmosphere. Joan Fontaine does a great job portraying the fear and uncertainty that comes with the exciting new period in her life, and Laurence Olivier balances his romantic and more chilling sides really well. It's a mystery thriller under the guise of a romance and I absolutely love it, one of Hitchcock's best. Should it have won: Only problem here is that Hitchcock wasn't given best director.
#13 The Deer Hunter (1978) - Phenomenal movie. I remember watching this for the first time and being surprised by how little happens relative to the runtime, but not in a bad way as Cimino's patient pacing allows everything to be developed thoroughly thus making the themes and relationships to be far more impactful. The first act in particular does a fantastic job of building the relationship between Robert de Niro's character and his friends. It almost works as a character study for him but through those relationships and the lasting impact of Vietnam. His performance is great but just one of many great performances, and Cimino's direction leads an expertly crafted anti-war film. Should it have won: Big yes, one of the greatest war films of all time.
#12 Lord of the Rings: The Return of the King (2003) - One of cinemas great achievements. This win feels like it represents the entire trilogy rather than just this film, but even looking at this one on its own this is a no brainer. Closing out arguably the greatest trilogy of all time, Return of the King delivers a perfect conclusion with some of the grandest scale we've ever seen on screen. The battles are show stopping, but the more intimate and emotional moments also work perfectly. Everything looks incredible from the sets and costume to the digital effects, and while it is lengthy every moment feels earned. I'm not even a die hard Lord of the Rings fan and I can without question say that this is truly incredible. Should it have won: This feels like a win for the whole trilogy, and it is undoubtedly deserving.
#11 Moonlight (2016) - This is proof that even on a small budget you can make something visually stunning. The blue colours and gorgeous shot compositions that dominate much of the film truly make it one of the most aesthetically enticing films I've seen in some time. Through three acts showcasing three different points in the life of Chiron, Barry Jenkins masterfully touches on race and homosexuality in a both haunting and tender way. I'll always love the first act most, but every piece of this and all three actors that play Chiron are incredible, and seeing how the events in the first two acts shape the man we see at the end really gives a haunting feeling to the story. I'll give some bonus points here as the main poster for Moonlight is one of my all time favourites, I think it's truly brilliant just like the film. Should it have won: This is a 5/5 movie for me, but it was up against two others in Arrival and La La Land. With La La Land being one of my all time favs, I would have definitely given that the win.
#10 The Silence of the Lambs (1991) - This is heralded by many as the first horror movie to win best picture, a sentiment I don't really agree with as I consider it much more of a crime thriller, but alas it's an incredible movie. Anthony Hopkins in such short screen time delivers one of the most iconic performances of all time. Don't let that distract from what Jodie Foster and Ted Levine are bringing though as each of them are also turning in masterful work. This is a fascinating crime drama with some moments of frankly brilliant tension, and whether you consider it horror or not the fact that a film dripping in rich tension like this won is pretty sweet. Should it have won: Yes, this is a super cool winner.
#9 Everything Everywhere All at Once (2022) - After basically sweeping the 2023 Oscars Everything Everywhere All at Once cemented itself as perhaps the weirdest movie to win best picture, and I mean that as the biggest compliment. The sophomore effort from the Daniels is one of the boldest swings to somehow hit I think we've ever seen, giving us a multiverse story focused on an immigrant family that has hot dog fingers and all-powerful bagels, that somehow just all comes together perfectly in something that is as emotionally resonant as it is audaciously out there. This came out early in 2022 and became the most talked about in the film world before winning best picture over a year after its release, despite tons of great movies coming after it. Michelle Yeoh finally got her time in the spotlight, Ke Huy Quan made his comeback, and we were all treated to one of the most unique and special movies maybe of all time. Should it have won: This is THE movie of 2022, if anything else won it would have just felt wrong.
#8 Oppenheimer (2023) - Our newest entry to the history books and a film I think is one of the best winners we've gotten. Christopher Nolan is the reason so many people around the world have fallen in love with cinema and seeing him take home some well earned Oscar gold was incredible. Oppenheimer may be his most epic work yet, delivering a three hour long biopic that is thrilling from start to end thanks in part to brilliant editing from Jennifer Lame, a pulsing score from Ludwig Goransson, and one of the best ensembles we've seen in some time led by Cillian Murphy's commanding performance. This was THE movie of 2023 so I'm glad it came out on top. Should it have won: My favourite of the nominees was Past Lives, but how can you deny this one.
#7 One Flew Over the Cuckoos Nest (1975) - This is simply one of the best movies we've ever gotten. This masterpiece from Milos Forman delivers a fantastic ensemble headlined by Jack Nicholson but still giving each character enough screen time to connect with them emotionally. Nicholson is phenomenal, delivering a charismatic performance that makes you fall for the character despite clear faults. Louise Fletcher's performance as Nurse Ratched is equally impressive, giving a conniving and formidable foil for our lead. Forman delicately balances so many different tones here, giving a final product that is somehow entertaining one moment, heartwarming the next, and then devastating in a short time. Superb writing, great cinematography, and a fantastic set only help add to one of the best. Should it have won: Tough competition but yes, this is an all time great.
#6 The Shape of Water (2017) - Since I started really getting into film this is probably the most excited I was for the best picture winner. Guillermo del Toro is one of my absolute favourite filmmakers and this is the perfect showcase for the beauty he finds in monsters, using a Creature from the Black Lagoon style creature to deliver one of the most swoon worthy romances in recent memory. From the beautiful blue colour scheme to Alexandre Desplat's sweeping score, this is one of the most beautiful films of the 2010s. The creature design is phenomenal, and Doug Jones brings a great physical performance brining the creature to life. Sally Hawkins is a delight in the lead, Octavia Spencer is a great supporting character, Richard Jenkins steals every scene he's in, and Michael Shannon is a perfect villain for this story. I just love being swept into the fantastical whimsy of this and it's easily one of my favourite best picture winners. Should it have won: You can easily make an argument for Get Out but this was my favourite of the year and feels more like an Oscar movie.
#5 Parasite (2019) - Like The Shape of Water this is one I got to follow along with the excitement of leading up to its historic win. I still remember the moment it took best picture where everyone I was watching the ceremony with jump up cheering as if we just saw a game winning touchdown. This was in the restaurant/bar on campus and even people not there for the Oscars seemed to be getting excited. All that excitement could not have been more justified, as not only is this the first international winner, but it's also one of the best movies we've gotten. Bong Joon Ho delivers a brilliant satire of class differences that is at times hilarious and at other times a bitingly sharp thriller. The screenplay is ridiculously good, and the ensemble is phenomenal bringing this great script to life. The production design is also so ridiculously perfect here, adding so much to the commentary while also working within the intricate set up of the film. I adore this movie, it seems everyone adores this movie, what an absolute masterpiece. Should it have won: Parasite winning was one of the most exciting Oscar moments I've ever seen, I wouldn't trade this one for anything.
#4 The Departed (2006) - I just love The Departed. This was the first Martin Scorsese film I ever saw and to this day it's my favourite. Narratively the diverging cat and mouse between two characters essentially pretending to be the other turns into a deliciously twisted web. Dicaprio and Damon are both terrific, but Jack Nicholson's supporting turn has to be the highlight performance. Shout outs are also do to Martin Sheen, Vera Farmiga, and Mark Wahlberg who all do great work as well. But really the star of the show is Marty in the director's chair, delivering something tense and thrilling but also pretty fun at times. It also looks incredible, one of the best crime dramas out there. Should it have won: My favourite film from one of the all time greats, a more than deserving and great to finally give Scorsese his flowers.
#3 The Godfather (1972) - I like The Godfather: Part 2 quite a bit and appreciate its craft deeply. I LOVE its predecessor though. The Godfather comes up often in the "best film ever made" discussion and I truly believe it belongs there. A true narrative epic that packs in so much rich storytelling surrounding a brilliantly written crop of characters. Al Pacino is phenomenal, acting opposite Marlon Brando and consistently holding his own which is a groundbreaking achievement on its own. I love James Caan as Sonny, I love Diane Keaton, and honestly there isn't a performance I don't enjoy in here. The cinematography is perfect whether it be in grander moments or more intimate ones, and there are just too many expertly directed moments that I adore to count. This is one of the best. Should it have won: Arguably the greatest film ever made so yes obviously this should have won.
#2 The Apartment (1960) - It feels almost weird to follow up something with the stature of The Godfather with what is essentially a romantic comedy, but I just love this movie so much. I mentioned earlier how big of a Billy Wilder fan I am and this is my personal fav of his. Jack Lemmon brings one of the most charming performance of all time to screen here, falling for someone and choosing to be there for her even when she's with another man. This is basically a film all about a man renting his apartment for people's adult pleasures, a pretty wild premise for the time and an even wilder premise for something so focused on its romantic side. Shirley MacLaine is enchanting, making Lemmon's character all the more believable, and Fred MacMurray is a lot of fun as the kind of scuzzy boss. Wilder's energetic filmmaking is all over this, bringing to life one of the most entertaining scripts out there in all it's fun and romance. This is such an easy film to fall for, I absolutely love it. Should it have won: It's the best movie of one of the all time greats, one of the most entertaining pieces of filmmaking out there and just an all around great movie, so of course it should have.
#1 Casablanca (1942) - And we finally arrive at the top. Casablanca is a perfect film if you ask me. It's technically a war film but operates on the edges of the war to give us a pretty perfect love story. We get the past and the present between Rick and Isla, making every moment between them hold so much history and the movie's iconic ending resonate on a deep emotional level. I'm obsessed with this script, telling the stories of our main characters so well while also leaving room for some really strong political tension. All one has to do is look for the most iconic lines in cinema and you'll know how great of a script this is, as there are almost too many great lines to count. The Moroccan setting and some great cinematography make this a visually stunning film from start to finish, especially in the moody lighting of the final moments. Humphrey Bogart is terrific in his broody leading role, but the hope filled performance from Ingrid Bergman is one of my absolute favourites. Over eighty years later and this film still manages to make me feel a wide range of emotions, and it stands strong as not only one of my favourites but one of the all time greatest. Should it have won: I can't think of a film that has held up quite as well as Casablanca. One of the greatest films of all time it absolutely should have won.
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