As we get closer to the 100th Oscars in just a few years, there is an already massive list of films. I have not seen every Best Picture winner, so a few simply just aren’t here because I didn’t watch them. others are perfectly fine films, but I would have picked something else. And a few, well, it’s OK to not like everything, even a Best Picture winner. While a list of the most iconic winners might be different, these are the ten films that strike my fancy the most.

#10- Kramer Vs Kramer (1979)

Director: Robert Benton

Cast: Dustin Hoffman, Meryl Streep

Winner of 5 Academy awards, Kramer Vs. Kramer is such a powerful character study. Certainly, there are plenty of those on this list, from the more recent entries like Nomadland and moonlight, to Terms Of endearment and ordinary People. But, for my money, I was blown away the first time I saw this. It is a complicated film for me, growing up a child of a single mother, but seeing all that Dustin Hoffman’s character does to try and normalize life for his son, only for his estranged wife to stumble back in creates such conflicting emotions. how dare she! After all this time. And yet, you don’t want to take away the opportunity for the boy to see his mother, but extenuating circumstances make this trial deeply complex. If you’re in for a character study, this is it. I’ve seen four of the five films nominated for Best Picture this year (including Kramer), and I would have voted for this over the extraordinary Apocalypse Now. We have so many war films, and Apocalypse Now might be one of the best, but the visceral nature of Francis Ford coppola’s direction keeps me from revisiting it. While Kramer Vs. Kramer is not a happy film, it is certainly an engaging one made better by performances from two of the best actors ever, and a rare Oscar nomination for a child actor.

#9- Chicago (2002)

Director: Rob Marshall

Cast: Renee Zellweger, Catherine Zeta Jones, Richard Gere, Queen Latifah, john C. Reilly

Winner of 6 Academy Awards, Chicago really kickstarted a new musical trend. We had a golden era of musicals that petered out during the 1970’s, leaving us with just a few notable works in the 80’s and 90’s. Even a film like Newsies was a financial failure, only later gaining success. But if Marshall hadn’t broken ground here, we might never have seen adaptations of Hairspray, Dreamgirls, the Phantom of The Opera, Nine, and others that kept pushing throughout the 2000’s. It has a very different style than the musicals of years past, and features likely the best work from its entire cast. Zellweger, Zeta-Jones, Gere, Latifah, and Reilly were all staggeringly good, and although not all recieved Oscar nominations, Zeta-Jones did walk away with an Oscar. Plus, of the other films up for best picture tht year, I really was not a fan of The Hours, and I can live with Chicago winning over Gangs Of New York and the pianist. The Two Towers wasn’t the right Rings film to win either, being the middle of the trilogy.

#8- The Lord of The Rings: return Of The King (2003)

Director: Peter Jackson

Cast: Elijah Wood, Ian McKellan, Sean Astin, Viggo Mortensen, Andy Serkis, Orlando Bloom

Winner of 11 Oscars, this win was for nerds everywhere. For every nerd who was angry at the exclusion of The Dark Knight, or the fact that no Star Wars film, no Indiana Jones, no back to The future, and no Marvel or DC movie has ever won the top prize, it is validating at least to see Jackson’s crowning achievement win an Oscar. it’s a great film, and the only reason i haven’t seen it more times than I have is due to the runtime. but lucky us, there are even longer cuts to enjoy. It’s a work of staggering genius, which quite frankly, Jackson has never been able to match again. this one was so hard to put here, because my heart is so much also with Lost In translation. Honestly, if either film had won, they’d be on this list. two of the greatest films of the 21st century, and possibly ever. The other nominees, Master and commander, Mystic River, and seabiscuit, I would say at least two of those would need to be kicked out in favor of nominations for Sideways and eternal Sunshine Of The Spotless Mind. I’d drop Master and commander and Seabiscuit, personally. Both are fine films, but 2003 was an incredible year in film. One ring to rule them all, one Oscar to bind them.

#7- Casablanca (1942)

Starring: Humphrey Bogart, Ingrid Bergman, Claude Raines

Directed By: Michael Curtis

Winner of 3 Academy Awards, Casablanca is just one of the greats. And, I was faced with that from a lot of films that people perceive as one fo the greats from the studio era. It is the oldest film on my list, notably because Citizen Kane is not a Best Picture winner, and Casablanca defeated nine films, and I bet you can’t name them off the top of your head. Casablanca feels like the foregone conclusion. If you took it out, what would have won? Heaven Can Wait? From Whom the Bell tolls? There isn’t a really strong runner up, and meanwhile, Casablanca is one of the greatest romances, most iconic films that ever was, full of great lines still quoted today. Casablanca has endured in ways I’m not sure most realize.

#6- The Departed (2006)

Director: Martin Scorsese

Cast: Leonardo DiCaprio, Matt Damon, Jack Nicholson, Mark Wahlberg, vera Farmiga, Martin Sheen

Winner of 4 Oscars, this is one of my favorite films of all time. I’d have it at number one if there wasn’t just that glimmer of reality that The departed won because Goodfellas did not. So, it isn’t Marty’s best, but it would be my #2 pick out of his career, and a damn fine film. It also has virtually no competition. The Queen did not need a Picture nomination, I didn’t care for Babel enough as a film, though I enjoyed the performances, and I think a lot of people forgot Letters From Iwo Jima. the only film anyone kind of talks about is little Miss Sunshine, and while I really liken that, it didn’t need the Best Picture trophy. This was an easy pick.

#5- One Flew over The cuckoo’s Nest (1975)

Director: Milos Foreman

Cast: Jack Nicholson, Danny devito, Brad Dourif, Louise Fletcher

Winner of 5 Oscar’s, this adaptation of the novel of the same name was bought by Michael Douglas who believed in making this film. He didn’t choose to star, nor did his father, instead they cast the pitch perfect Jack Nicholson, and history was made. Also, Louise Fletcher in her Oscar winning turn as Nurse Ratched really stands as a top win in Supporting Actress. Now, this one is a son of a bitch, because the Picture lineup is stacked.truth be told, i haven’t seen one of them, but the titan here is Jaws. Jaws would have been an excellent winner. Dog Day Afternoon would have been solid, though I’m not crazy about the LGBTQ representation in that film. So, my ballot struggle would be this versus Jaws, and if I could do it all over again, I’d give this the Best picture trophy, but give Spielberg the Director trophy to kickstart his long career. Not that he needs another Oscar, but his revolutionary and sometimes dangerous way of filming is why Jaws is extraordinary. that being said, Cuckoo’s Nest is a perfect use of Nicholson, and a brilliant exploration of mental health.

#4- American Beauty (1999)

Director: Sam mendes

Cast: Kevin Spacey, Annette Bening, Thora Birch, Wes Bentley, Chris Cooper, Mena Suvari

Winner of 5 Oscars, American Beauty had some interesting competition. they are all good films, and movies I like. the only one it feels like anyone would fight for is The Sixth Sense. American Beauty benefitted from tht year not having to compete with The Matrix or Toy Story 2, both of which have stood the test of time critically and with audiences. American Beauty is one of my favorites, and I remember where I was. I can picture the theater I saw it in, not just the movie theater, but the actual screen. it is kind of a dark comedy, and it represents a bit how film evolved into the 90’s, and gave us a glimpse of what would come in the 2000’s. A great transitional film.

#3- The Sound Of Music (1965)

Director: Robert Weiss

Cast: Julie Andrews, Christopher Plummer

Winner of 5 Oscar’s, this is one of the golden age musicals I was talking about. watching Julie Andrews run up that hill is oddly satisfying. In High School, I was Max in a production of the Sound Of Music, so it is even nearer and dearer. It is timeless, and the competition was It also really only has one contender to discuss, Dr. Zhivago, and I’d easily choos the hills being alive over that.

#2- The Godfather (1972)

Directed By: Francis ford Coppola

Cast: Marlon Brando, Al Pacino, james Caan, Diane Keaton, Robert Duvall

Winner of only 3 Oscar’s, The Godfather is deeply iconic. And, I do actually prefer the first to the second, so this was an easy choice. But, what a flex to have Oscars for two out of the three parts, and have your franchise be the first to have a sequel win. Brando is perfect, Pacino is just kicking off his excellence, and James caan was a perfect choice. I know cabaret had fans, but come on. You leave the gun, and you take the cannoli. The Godfather is that cannoli.

#1- Schindler’s List (1993)

Director: Steven Spielberg

Cast: Liam Neeson, Ralph Fiennes, Ben Kingsley

Winner of 7 Oscars, and Steven Spielberg’s best Picture winner so far, Schindler’s List had to be here. Like, how could I argue against its win? The Academy made it really easy for me by not putting my true #1 favorite film of all time in the Best picture lineup, Jurassic Park. Just time travel back to 1993, and realize that in the same year, Steven Spielberg likely put out two of the best films of his career. ever. He hit with one of the most iconic and influential blockbusters, and came in with a devestating war film that redefined what a war movie could even be. What it could even show. it instantly became required viewing, and ran uncensored on network television throughout the 90’s. Uncensored. Unheard of. but, what really put it on top is that I wouldn’t vote for any of the other nominees, and Spielberg did direct a second film that year that was my favorite of all time. he should have two Best Picture nominees in the same year. 1993 was the year of Spielberg, and Schindler’s List is my pick for my favorite Best picture win of all time.