26. Dr. Strangelove Or: How I Learned to Stop Worrying and Love the Bomb (1964)
One of the funniest and most unlikely satires ever made, Dr. Strangelove is just as relevant and powerful today as when it came out, a landmark even more notable for the fact that it debuted almost 50 years ago. Dr. Strangelove would be landmark filmmaking in any era (“Mein Fuhrer” stands as one of the best movie lines in history), but in an era tinged with so much cultural repression, this movie is nothing short of a miracle.
27. Diva (1981)
If Diva is an exercise in style, you don’t get filmmaking more gorgeously chic than this epitome of 80’s cinema. Like a French American Gigolo, Jean Jacques Beneix’s thriller masterpiece eschewed realism for a cinema du look, obsessed with surfaces. It’s visually inventive from top to bottom and would herald the later stylistic conventions of David Lynch. But despite its liberatory sense, the film’s heart is rooted in French cinema history, like a Diabolique for the decade of excess.
28. Drive (2011)
A perfect companion film to Diva, Nicolas Winding Refn’s punishing opus is bloodshed turned up to 11, the ultra-violence of which Kubrick dreamed. Whereas most films (see: World War Z) play down the human cost of violence, Drive crushes you with raw feeling. Although the movie is criticized for its arty detachment, Drive’s style offers the perfect juxtaposition, pulling you out of the narrative when you need a little distance. And if distance comes in the form of a glittery snyth soundtrack and Ryan Gosling at his most Brandoesque, you could do worse.
29. Duck Soup (1933)
The Marx Brothers’ catalog is a comedy fan’s wet dream (between Monkey Business, A Day at the Races and A Night at the Opera), but Duck Soup stands alone for being totally committed to its geopolitical farce. Like Chaplin’s The Great Dictator, the film has a lot to say about the surrealism of nationalism and warfare, like a Catch-22 in miniature. For fans of the similar The Producers, check this out to see the guys who helped Mel Brooks exist.
30. Election (1999)
Still Alexander Payne’s finest work, Election shined in a particularly strong year for American film (against the underrated Magnolia and Three Kings) and stands as one of the best movies ever made about high school. Election brought back Matthew Broderick and gave the world Reese Witherspoon — about whose performance enough nice things cannot be said. To me, Tracy Flick will always be the greatest movie character in history, a satirical creation so ingenious particularly because it feels so real.
Note: Make sure to check out Tom Perrotta’s source novel, just to see how totally different it is.
31. Eternal Sunshine of the Spotless Mind (2004)
Eternal Sunshine is one of the chic picks for movie of the 2000’s, which is hard to argue against. Like Radiohead’s OK Computer, it’s a perfect encapsulation of our post-industrial ambivalence, a society that worried it was losing its soul to technology. Of all of Charlie Kaufman’s many cinematic experiments, Eternal Sunshine is his grandest because of the poetry lurking beneath. Although it takes its name from Alexander Pope, Kaufman writes some beautiful verses of his own, a feedback loop of romance at its most tragicomically human.
32. The Exorcist (1973)
Always the cinematic prankster, William Friedkin’s dada stunt is still the scariest movie ever made, a movie that’s vile, vulgar and absolutely horrifying. Forty years later, it’s DIY effects are as convincing as they were in the 1970s, showing that blood and guts do not always terror make. Sometimes all you need is a little pea soup.
33. Fargo (1996)
It’s hard to pick one Coen Brothers film from a catalog so ridiculously stacked (if you haven’t seen Blood Simple or A Serious Man, why?), so I picked two for this list. While still being their finest film, Fargo was my first intro into the Coens, an epitome of every reason they are some of the best filmmakers alive. If you aren’t ludicrously excited for Inside Llewyn Davis (due out this Fall), I don’t want to know you.
34. Fitzcarraldo (1982)
Like Aguirre the Wrath of God, Werner Herzog’s magnum opus is cinema at its most messianically ambitious, a perfect companion to the more lauded Apocalypse Now (one of Coppola’s many masterpieces). The behind the scenes story of the film is just as fascinating, chronicled in the documentary film Burden of Dreams, in which Herzog has a breakdown and becomes just as hopelessly deluded as his title character. It’s the perfect iteration of life imitating art and a must-see for anyone who wants to make movies.
35. Flirting with Disaster (1996)
For those who loved Silver Linings Playbook and The Fighter, Flirting With Disaster is a screwball celebration of David O. Russell’s mad genius. While being a flawless interpretation of the Preston Sturges road comedy, Flirting With Disaster is wonderful in its own right with a game cast nailing its mile-a-minute script. While getting the best possible use out of Ben Stiller, it proves what an underrated comedienne Tea Leoni is, as the adoption agent helping stiller track down his birth family. Wes Anderson’s great The Royal Tenenbaums may have done dysfunction more famously, but Flirting With Disaster got there first.
36. Gates of Heaven (1978)
Not to be confused with Heaven’s Gate, Gates of Heaven is a one-of-a-kind masterpiece from Errol Morris, the reigning king of the documentary form. Like Fast, Cheap and Out of Control and Tabloid, this one of Morris’ quirky entries about everyday eccentrics. Gates of Heaven is about the relationship that people have with their pets, and it’s strange, challenging and sure to provoke debates amongst your friends. Is Morris celebrating his subjects or making fun of them? You decide.
37. Ghost World (2001)
Terry Zwigoff hasn’t made a film in nearly a decade, but before the wasteland that was Art School Confidential, Zwigoff had an amazing streak with Crumb, the underrated Bad Santa and Ghost World, the critically championed indie gem based off Daniel Clowes’ comics. Ghost World is truly inimitable, a coming of age story that’s both a sharp satire of conformity and the art world (Illeana Douglas kills in a small role) and a loving ode to the struggle to find your own voice. It’s also notable for giving Scarlett Johansson her breakout role.
38. The Godfather (1972)
What can I say about The Godfather that hasn’t already been said? Considered by many to be the greatest American film, the film is a triumph of the studio system, the film that paved the way for big budget art movies (you’re welcome, Inception). Although it’s popularly accessible, The Godfather is a searing commentary about American capitalism and the way big business corrupts. In addition to making Apocalypse Now possible, it paved the way for Part III, when Coppola lost his mind and cast his daughter, Sofia, in the film. She later became a great director, but she’ll always be infamous for giving what may be the worst performance in the history of film. It needs to be seen to be believed.
Extra Credit: Goodfellas, Scorsese’s wildly inventive and iconic take on organized crime.
39. Hannah and Her Sisters (1986)
Although the Woodman is mostly known for his 70s contributions, Hannah and Her Sisters proves Woody was at his finest during the 80s, when he churned out Radio Days, Zelig, Another Woman, The Purple Rose of Cairo and Crimes and Misdemeanors. Hannah was mid-period Woody at his most literate, warm and wise, pulling together one of the finest casts ever. Dianne Wiest is the stand out, playing a Woody Allen foil just as neurotic and lost as he is. Wiest might be better remembered for killing it in Bullets Over Broadway, but her unforced naturalism here is particularly refreshing against the Allen artifice.
40. Harold and Maude (1972)
One of the greatest love stories ever filmed, Hal Ashby’s March-December romance is a movie that challenges so many of our assumptions both about love and comedy. Ashby dares us to fall in love with what makes us uncomfortable and laugh at our darkness. Like Wristcutters: A Love Story, it’s a romantic suicide comedy that’s pitch black (multiple scenes ask us to laugh at the sight of a noose), frank and unexpectedly moving.
41. The Heartbreak Kid (1972)
Because of it’s similarities in tone and style to The Graduate, the directorial debut of Elaine May (who wrote the earlier film) often gets forgotten about. May has had a rough go of it in Hollywood between the colossal flop of Ishtar (which I actually liked) and the terrible remake, but this movie proves what a talent she was. Like Portnoy’s Complaint, The Heartbreak Kid a brutal (and very hard to watch) satire of Jewish masculinity of the era, about the affair between the married Jewish guy and the shiksa that catches his eye.
It also started my strange attraction to Charles Grodin, which I can’t explain. The heart wants what it wants.
42. Heathers (1988)
The best comedy ever made about high school (and Mean Girls’ kooky cousin), Heathers became a cult classic after being a major failure in the theatres, mostly because it’s target audience had no idea what to do with it. Originally conceived as “Full Metal Jacket for high school,” Heathers is a sharp departure from the Breakfast Club-era of bawdy coming-of-age films with a sweet center. Heathers’ heart is pure black, a wry look at teenage sociality and suicide, and the side effects of popularity. Hint: contents may contain poison.
43. High Fidelity (2000)
One of the quintessential Chicago films, Brit Stephen Frears (The Grifters, Dangerous Liaisons) brings Nick Hornby’s book to the big screen in a way that absolutely stands up the original. It’s like hearing a great cover of a song you really loved only to have your appreciation for the original deepen and grow.
44. His Girl Friday (1940)
The fastest comedy ever made, Howard Hawks rapid fire comedy classic had so much dialogue in it that the actors had to step on each others’ lines to get all of it in. It sounds like a brain freeze, but Rosalind Russell and Cary Grant are such pros that it all goes down smoothly.
45. Hoop Dreams (1994)
A solid pick for the best film of its decade (along with Pulp Fiction), Hoop Dreams is the documentary equivalent of the great American novel, a sprawling, three-hour epic that stands up to the best of Steinbeck. By Steve James (also of the great The Interrupters), the film follows two young men who dream of becoming NBA stars and what happens when those dreams are deferred. They explode into one of the greatest films ever made.
46. In the Mood for Love (2000)
Roger Ebert once claimed that film, at its best, evokes a sense of mood; his favorite films (Apocalypse Now, Aguirre, the Wrath of God) lingered over him like a foggy haze. As a filmmaker, Wong Kar-Wai (2046) is all mood, all the time, and In the Mood for Love shows his fog as its most transcendent. A panoramic visual feast, it’s like the wallpaper scene from Garden State spread out to two luscious hours.
47. Jules and Jim (1962)
Truffaut was a new wave master, and half of his films deserve recognition on this list (especially The 400 Blows and Day For Night), but Jules and Jim has remained iconic in a way many of his other films haven’t. There’s a big reason: Jeanne Moreau, giving an alluringly complicated performance that speaks to how we feel love. It’s painful and tragic but casts a spell you wouldn’t dream awaken from. As far as love triangles go, this will forever be cinema’s finest.
48. Kicking and Screaming (1995)
Noah Baumbach is better known for Greenberg, The Squid and the Whale and this year’s Frances Ha (a resplendent little gem you need to see ASAP), but Kicking and Screaming was both his first film and still his best. A who’s who of early 90s indies, Kicking and Screaming stars Chris Eigeman, Parker Posey, Josh Hamilton, Carlos Jacott and Eric Stoltz as a group of college graduates who can’t leave campus life behind. If you want to see how Lena Dunham came to exist, look no further than Noah Baumbach. He invented her.
49. Killer of Sheep (1979)
Like Army of Shadows, Killer of Sheep only recently got its due after being released in 2007. Killer of Sheep evokes the later work of David Gordon Green, whose George Washington is a spiritual successor to Charles Burnett’s work. This collection of vignettes evokes an almost avant garde, stream of consciousness feel (ala Maya Derren) that gives us a sense of just stumbling into this young boy’s life.
50. L.A. Confidential (1997)
If not for Titanic steamrolling over everything, L.A. Confidential would have won everything in sight at the ‘98 Oscars, but had to settle for a Best Supporting Actress win for Kim Basinger. Curtis Hanson had other fine works later (like the ever lovely Wonder Boys), but this is Hanson at his finest — sprawling, meticulous and a flawless evocation of its genre. For anyone in love with noir, L.A. Confidential reminds you exactly why.