I'm a sucker for anything funny but sad. My favorite is Royal Tenenbaums. A close second is Fletch. And last is a revolving door. Sometimes The Departed, sometimes Igby Goes Down, All Coen Brothers, Basquiat, etc...
Side Note - I've cried every time I've watched Man On The Moon. I know the movie compounded all the drama in a few short scenes, but he died on my 6th birthday. Just always been enamored. Do you have a movie like that?
Maybe not the best or my favorite, but pretty good
I really like The Royal Tenenbaums too, I watch it almost everytime it's on. I also love Wes Anderson's Bottle Rocket, which has the Wilson brothers too. It's hard to pick one favorite movie, but I'll say my favorite war movie is Platoon.
I have a hard time pinning an all time favorite, but I absolutely love just about every movie Wes Anderson and the Coen brothers have put out. I can't even say I have a favorite comedy; there's so many different types of comedies I feel it's unfair to judge one against another.
I will say this, I recently watched Freddy Got Fingered - it was the first time I watched it in about ten years - and laughed my fucking ass off! I know a lot of people hate that movie, and think it's the worst film ever, but excepting it for what it is, I honestly think it's one of the funniest movies ever made.
I remember seeing it when it first came out, I thought it was Okay, but there were a lot of scenes I couldn't even watch. Seeing it now, I find all those horrible scenes utterly hysterical, which makes me believe it was a comedy way, WAY ahead of it's time.
Going Berserk was great. The fake movies were hilarious. The funniest movie I've seen is Raising Arizona. He was wearing his goddamn jammies. They had Yodas and shit on'em.
Barfly is also fucking great.
E.T. : The Extra Testicle!
No.... Honestly.... E.T. : The Extra Terrestrial, was an awesome flick, and the very first movie that I viewed at an indoor theater. (I was at a few Drive Ins Before then).
9. Cry Baby
8. The Station Agent
7. Ghost World
6. Blue Velvet
5. Duck Soup
4. Pee Wee's big adventure
3. Cabin Boy
Jack and Jill starring Adam Sandler............lol