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My all-time favorite movie to watch while tripping is got to be Speed Racer (2008).
Its made from the same makers of The Matrix Triology (not a good trippin' movie, tell ya why later....). Its a little bit of a kids movie, but it does have some adult themes too like attempted murder with a vechical and Matrix-style gun-shooting scenes. But MAN, the best part is the over-saturated brillant psychedelic colors/special effects and very-fast paced action scenes. I saw it on shrooms and 1/2 hit of acid at the theaters, it practically blew my mind. Especially the ending when they look thru Speed Racers eye's, its almost like they made it for people to watch on psychedelics.
Another good trippy movie is Memento. Its a unique movie because its about a guy who has a mental disorder where he cannot make new long-term memories from his short-term ones (anterograde amnesia). The makers of the film simulate this for the audience by having 2 plots going on simultaneously: one is played in the correct chronological order in black-and-white, while the other is spliced in between scenes and played chronologically "backwards" in color. So its like you see the end in the first part of the movie and see the middle at the end of the movie. Great to watch while trippin'.
The Matrix is NOT a good movie to watch trippin'. Its got some pretty trippy themes/ideas/philosophies that could blow your mind but the tone of the movie is very dark, distrubing and depressing. I watched it on Morning Glories, and that part when they extract that machine/live worm thing from his stomach disturbed my trip so much, I had to turn it off.
One more thing: good idea for a post Big Chief. I wish I would have thought of that.