Big Fish rocks on 4 position tryptamines. It is such a magical fun film and had me almost in tears a few times. Akira, if you can handle it gos great with lsd. Anything with a good vs. evil epic battle, especially involving heaven and hell scenarios will blow your mind.
I've been doing alot of tripping by myself recently, cause of my relocation, and netflix has become my new tripping buddy. If you want to laugh your ass off at the shear surreal ridiculous nature of something, watch Mr. Show w/ Bob and David. These guys have admitted to eating mushrooms and acid, and are pro-drugs, so they know what's funny while tripping.
The simpsons have always been fun to watch tripping, cause you can see each individual frame which is cool. I tend to stay away from dark evil movies while tripping as I like to be in good spirits. It may sound corny, but Where the Heart is is a good emotional movie that will have you crying.
Death to Smoochy is a must see for any movie watching tripper. It is so ridiculous that it'll have you saying,"What The Fuck!!!"
Almost anything by Tim Burton is good.
I watched Natural Born Killers tripping recently and it wasn't really a good movie to watch tripping, but I finally understood what he was saying about America and how fucked up of a country we are. Speaking of that, my cousin finally got me to watch Bowling for Columbine, and I was tripping. That movie will open your mind. We are so pre-programmed in this country and we don't even realize it. That movie opened my eyes as much as any hardcore psychedelic can.
Big Fish, Mr.Show, and Death to Smoochy are must see movies/shows though, trust me you will not be dissappointed.