21. The Apartment
Director: Billy Wilder
One of the loneliest movies I've ever seen, The Apartment is often labeled a comedy. It is funny, I suppose, but not a laugh riot. Jack Lemmon gives his best performance in the role of corporate climber CC Baxter who focuses on his career to distract him from how alone he is. Fred MacMurray is hateable but completely real as the empty boss who takes up with whatever pretty young thing will have him to keep him away from the unhappy marriage he's been trapped in for years. And Shirley McLaine is wonderful as the depressed elevator operator who is currently hooking up with MacMurray while being pined for by Lemmon. This portrait of these 3 isolated people is surprisingly effective, I think because it looks at loneliness in different ways, because these people aren't lonely in the same way or for the same reasons. Add onto that that Billy Wilder was a tremendous and entertaining filmmaker and so this movie is as well, and you have one of the best movies I've ever seen, and one that really blew me away when I saw it. It felt like the kind of movie people complain that Hollywood never makes or that doesn't win awards or that doesn't connect with audiences. This movie did all of those things and easily deserves its place in the popular canon of films.
22. Aguirre, the Wrath of God
Language: German (though shot in English for financial/contractual reasons, Herzog considers the German language version truer, and I agree)
Director: Werner Herzog
Werner Herzog's first movie with the towering talent and even larger ego and just plain insanity that was Klaus Kinski, Aguirre was an obvious influence on Coppola's later Apocalypse Now. Poetic, horrific, hallucinatory, and nightmarish in its descent into madness alongside its title character, Kinski's Aguirre. Like all Herzog movies, the images it contains are wondrous and occasionally overwhelming in their impact. The opening shot of thousands of people walking down one hill only to be walking up another (where the camera is) while on a steep hill with gorgeous (yet ominous) fog collecting to the side of the screen. The final moments of Aguirre, alone and surrounded by chattering monkeys while he mutters to himself of his greatness. These by themselves would make for a tremendous movie, but when contrasted against each other, and separated by many other brilliant scenes (including one darkly comical moment when a man is beheaded and his head, laying in the dirt, finishes its sentence anyway) make this the master filmmaker's highest achievement, one of the great movies ever made.
23. Singin' in the Rain
Director: Stanley Donnen, Gene Kelly
I don't love musicals. I grew up watching them with my mom, who loved them, but I generally just thought "meh." But when it comes to Singin' in the Rain, what's not to love? Gene Kelly is as charming as he can be, Donald O'Connor is like a walking cartoon, Debbie Reynolds is as plucky as anyone has ever been, Jean Hagen is hilarious and hissable, the script is light hearted and fun, it's gorgeously made, and the songs are pretty good too. As usual, the only negative was the big dance number Kelly threw in at the end of the movie, killing the narrative momentum and unnecessarily padding the runtime. Still, when Debbie Reynolds tries running away and Gene Kelly shouts to the audience "stop that girl, that girl running up the aisle. Stop her! That's the girl whose voice you heard and loved tonight. She's the real star of the picture. Kathy Selden!" the way it's staged and filmed is simply as perfect a moment in movie history as has ever existed.
24. Monty Python and the Holy Grail
Director: Terry Jones, Terry Gilliam
I just wrote about this one in the Top Comedy films list, so I won't bother writing much more. I will just say that it's one of my most viewed movies and yet it still makes me laugh every time.
25. Rio Bravo
Director: Howard Hawks
Despite its nearly 2 1/2 hour runtime, Rio Bravo just flies by when I'm watching it. Howard Hawks famously said the secret to a great movie was "3 good scenes and no bad scenes." That's exactly what he gave us over and over again, but Rio Bravo is his masterpiece. John Wayne's best performance is still in The Searchers, but this is his best movie too. But to me, the standout of this movie is Dean Martin. Martin, as the recovering drunk deputy Dude, gives a performance of pain, danger, humor, warmth, and intelligence. He should've had an Oscar for it. Wayne is as good as he always was, and this is one of the few times he had really good writing to work with. Of course, at its core it's a "John Wayne movie" and he carries it like few other stars in Hollywood history could've. Angie Dickinson, Walter Brennan, and even Ricky Nelson give good supporting work. Even the scenes of Nelson and Martin singing, during the "calm before the storm" section, don't feel shoehorned in. These characters would need to occupy themselves somehow, and this seems a perfectly fine way to pass the times. Hawks liked the movie and Leigh Brackett's script so much he loosely remade it twice, in his last two movies El Dorado and Rio Lobo. Reportedly, when Hawks asked Wayne if he wanted him to send over the script of Rio Lobo for approval, Wayne responded "Why? We've already made the movie twice." But, obviously, Rio Bravo is the crown jewel.