49. Harvey (1950)
One of the most ingenuous films ever made. It’s so simple that you can’t help but love it and get caught up in all of its saccharine glory. It’s the cinematic equivalent of cotton candy, except for the part where cotton candy tastes like shit. This actually tastes good.
48. Who’s Afraid of Virginia Woolf? (1966)
If “Harvey” is the cinematic equivalent to cotton candy, then “Who’s Afraid of Virginia Woolf?” is like drinking a shot of straight scotch. It’s rough, strong, and can leave you with a bitching headache if you think about it too hard, but all the same, it goes down pretty damn smooth. This was Mike Nichols debut movie as a film director and it’s quite clear that all of the massive talents he fine tuned in the theatre, he brought with him to his new career in the movies. The acting is flawless, and to this day, “Virginia Woolf” is still one of the only movies to have its ENTIRE cast nominated for Academy Awards. (True, that’s only 4 people, but still.) If you like “small” movies, and vindictive party games, it doesn’t get any better than this.
47. Zoolander (2001)
When eulogizing his fellow roommates/male models, Derek Zoolander says: “It’s not their fault that they died in a freak gasoline fight accident.” I don’t think you could sum up the humor of this film any better. It’s absurd, stupid, disgusting, and absolutely hilarious, meaning there’s something here for everybody to laugh at. It’s easily one of the best comedies of the past couple decades. Now bring us that sequel already Ben.
46. High Fidelity (2000)
“High Fidelity” is probably the best movie about music and relationships ever made. I understand that that is highly specific, but even individually in both categories, “High Fidelity” ranks highly up there. (No pun, seriously.) John Cusack plays the role he does best, the everyman, but this is easily his best interpretation of the role. The music is simply fantastic, the jokes are funny, and any movie that mentions “The Evil Dead II” is a winner in my book.
45. The Untouchables (1988)
Forget “The Godfather”, “The Untouchables” is the best gangster movie of all time. It might not have the literary depth of Coppola’s classics, but what it lacks in that department it more than makes up for in thrills and entertainment value. The entire film is one awesome scene after another, punctuated with awesome action scenes directed by Brian De Palma and snappy dialogue written by David Mamet. It’s a gangster film fused with western sensibilities and envisioned as pop art.