24. Ghostbusters (1984)
“Ghostbusters” has probably been one of my favourite movies of all time for longer than any other film. I’ve loved this movie since I was four years old and it’s entirety is more or less completely visible in my mind’s eye. It pretty much represents the pinnacle of what was going on in the comedy world at the time it was made with both Bill Murray and Dan Aykroyd, making “Ghostbusters” one of the most entertaining films ever made.
23. Leon (1994)
“Leon” is quite possibly the most intriguing “action” film ever. I say that because really, it’s quite light on the action, (though the scenes that are there are jaw-dropping in their execution) and heavy on its character development. By the time “Leon” finishes you really care for the characters that inhabit its world, and hope more strongly than usual, that good will triumph over evil. And yes, it doesn’t hurt that Natalie Portman is in this film, eleven years old or not.
22. American Psycho (2000)
Most people are always going to remember and love Christian Bale for his performance as Bruce Wayne in Nolan’s Batman films. I, on the other hand, am always going to remember him as Patrick Bateman in “American Psycho.” It’s equally one of the most disturbing and funny (yes, funny!) films ever made. The entire film can be viewed as a horror film, or as a dark comedy, or as both, and no matter what way you choose to look at it, it works 100% of the time. (Personally, I like looking at it as a very dark comedy.) There are so many fantastic scenes in this film that it’d be impossible to talk about all of them here, so just go out and watch it already.
21. Punch Drunk Love (2002)
“Punch Drunk Love” is probably the craziest romantic comedy you will ever see. At its heart, it’s probably an anti-romantic comedy, but it’s much more effective in making you care for its characters than most Rom-Com’s are. Not only is it beautifully shot, but it has a heartbreaking performance from Adam Sandler that is easily his best of all time. It’s really too bad that no other filmmakers have ever let Sandler go to as dark a place as Paul Thomas Anderson lets him go here, but then again, most filmmakers aren’t Paul Thomas Anderson. If you’ve ever hated yourself and hoped to be found redeemable through love, “Punch Drunk Love” is for you.
20. Funny People (2009)
From one Adam Sandler film to the next, “Funny People” is probably the greatest movie about comedy ever made. That’s not to say that it’s the funniest (though it is pretty funny) only that, no other film has really looked at the toll it takes on a person whose job it is to make other people laugh. Comedy is often a tool for self-defense more than it is anything else, and this film drives that point home. All of the people in this movie aren’t only funny, they’re lost and in need of help. It’s a fantastic story, told by Judd Apatow, the best comedy filmmaker we have working today.