I've got a whole list of popcorn movies or guilty pleasures or what have you that I could watch over and over again. Stuff like Airplane!; Lock, Stock, and Two Smoking Barrels; No Blood, No Tears; The Bride with White Hair; and Raiders of the Lost Ark, and various other action/comedy/fun flicks.
But for the sake of this question I'll focus on movies that moved me, or challenged me in some way. A great example is Mullholland Dr. I could watch that over and over and over and still feel like I'm watching something new. Ditto Pulp Fiction. The first time I watched The Pillow Book (as a rental), I wasn't sure what I had just watched. It kept me up all night thinking about it and the next day I went back to Blockbuster and rented it again to further explore it.
Comrades, Almost a Love Story--have probably watched this more than any other movie.
Crouching Tiger, Hidden Dragon--a movie that opened up a whole new world for me.
A Tale of Two Sisters--gothic psychological horror that works on many many levels. This is probably my second favorite movie of all time.
The Mystery of Rampo--beautiful and complex
And I'll throw in Goodfellas, Kill Bill, and Sin City for good measure.
One movie I haven't seen mentioned here yet (and one seen by very few people I know) that I could watch many times over is Life As A House. Not a comedy, though there are some funny scenes. It actually is a drama, so have to be in the mood for that, but I've never gotten sick of that one.
A few others off the top of my head would be:
Pan's Labyrinth
Eurotrip
Elf (required watching around Christmas)
Rat Race (Still need to replace my damaged copy of this one)
WARNING!!! WARNING!!! DO NOT VIEW THIS SPOILER! YOU HAVE BEEN WARNED!!!
Rat Race (Still need to replace my damaged copy of this one)
I believe Rat Race was the last "Laugh so hard your guts burst" film I've seen. The humor of modern comedies rarely level up to the feeling I got the first time I watched this.
Oh, forgot to mention What About Bob? Absolutely hilarious movie
Without doubt on that one. Also agree with Rat Race.
For me comedies are a never ending source of pleasure. The American Pie's, Office Space, Caddyshack, Animal House, Sex Drive etc. Also like the standups.
Non-comedies I always flip to are the Iron Man movies (because what is better than a drunk guy in a metal suit blowing stuff up?), Any Clint Eastwood western, Independence Day for some reason, 61* and a few other baseball movies, stuff like that.
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