Inspired by @ListPrompts. I didn't give a ton of thought to the order. But #1 is definitely the best.
  1. Honorable Mentions
    Dirty Harry, The Fugitive, Moulin Rouge
  2. Mean Girls
    Brilliantly written and unique and everything wonderful about Tina Fey.
  3. Master and Commander
    That bit where the other ship gets spotted on the other side of the island... Also one of the greatest soundtracks of all time.
  4. Fantastic Mr. Fox
    Probably the most overlooked Wes Anderson because it's based on a kid's story, but in terms of uniqueness and creativity in interpreting and adapting the story, this stop-motion film is his best. Even better than the Midnight Coterie of Sinister Intruders.
  5. Apocalypse Now
    Often hard to watch but brilliantly brutal reminder of some of the darker bits of popular humanity.
  6. Close Encounters of the Third Kind
    I saw a few clips on television of the early parts (the scene with the clay model, a few others) when I was young and was captivated by them. The full movie is beautiful and please don't ever watch the version where they show the aliens at the end.
  7. Airplane!
    The "drinking problem" bit makes me laugh even when I just think about it. Every time.
  8. School of Rock
    Perfect script with the only role Jack Black ever should have played. Linklater perfection.
  9. Metropolis
    A bit odd for the modern and non-German audience but beautiful and remarkable. It's got some New Hope style moments of "Holy crap how did they do that without computers!?"
  10. Ferris Buller's Day Off
    💯 Performance by Broderick. Fantastic montage of Chicago. The Art Institute sequence alone puts this film on my list. The turning point of John Hughes films where he started to drop the weird parts that only made sense to him.
  11. The Truman Show
    Perfectly unique execution of a concept that could be done lamely very easily. Bonus points for having a cameo by Philip Glass.
  12. Dead Poet's Society
    💯 everything. From the story to the cinematography to performances by all.
  13. Back to the Future
    This film makes no sense (Read: John Mulaney New In Town) but I think every human loves it to death. Best film of the 1980s.
  14. Vertigo
    My favorite Hitchcock (because Jimmy). Makes the list because of Saul Bass opening credits alone.
  15. Inception
    Sometimes the Nolans got ahead of themselves and made beautiful movies with lots of holes (looking at you, Interstellar) but sometimes they made Inception, which is flawless. And has that hallway zero-gravity scene.
  16. Forest Gump
    It is perfect. Best Actor of all time.
  17. The Empire Strikes Back
    Flawless in every way.
  18. Up
    Makes you cry in the first 10 minutes, makes you laugh for the rest. Oh you cry more too.
  19. The Shining
    The imagery in this film is like no other film. Kubrick's take on the story is as unique and interesting as Shelly Duvall's eyes.
  20. Momento
    If you like puzzling non-linear films with minimal characters and locations, this is the greatest one ever made.
  21. Duel
    This is a seldom seen made-for-TV movie directed by Spielberg in the 70s that you must watch. Often deep referenced in smart shows like Bob's Burgers (the one with the candy cane truck!).
  22. Fargo
    Best ending to a movie EVER. How can a movie with so much gore bring me so much joy?
  23. Toy Story
    Hands down the most creative, lovable film ever created. The imagery in this film is ingrained in my mind. The story is perfectly crafted like a Calatrava building but overflowing with hilarious bits and whimsical turns. Furthermore, the story of its creation and the extreme technical achievement of its creation is noteworthy enough.