I don't watch any movie over and over anymore. But when I was a kid, I watched the Ninja Turtles movie every night for what seems like months. . .and for a while, I also watched Robin Hood: Prince of Thieves every night for a long while. Really seems strange to me now, but I guess when you're 11 years old or so, you don't get sick of things very easily. . .or at least I didn't, apparently.
In no particular order: Transformers (naturally!) Alien Aliens Terminator 1 & 2 Star Wars 1-6 Indiana Jones 1-3 Superman 1, 2, Returns Batman Begins Spider-Man 1 & 2 John Carpenter's Halloween (every 31st of Oct.)
Both Transformers of course Lately we have been rotating through, 4o Year old Virgin, Knocked up and Superbad for late night viewing after the kids are asleep. The Spider-mans Fight Club, Baseketball and South Park movie used to be in heavy rotation durning "the bar days"
Back in 2002 and 2003, I used to watch every movie I owned (on VHS, even after my parents bought a DVD. I would not be easily swayed until I bought Endless Waltz on DVD, then I was in love in with DVDs, but used VHS still to record things), and talked about them constantly. I rented movies and kept them for weeks, watching them over and over again. Its only until 2004, that I became extremely embarrassed by my antics back when and I went red in the face every time I thought of that movie I watched a Billion times. I still can't watch the 1st Spider-Man without blushing with embossment over my obsession with it. 1. The Lord of the Rings: The Fellowship of the Ring [Theatrical Version] 2. Spider-Man 3. The Faculty 4. The Mummy Returns 5. Rush Hour II 6. Lethal Weapon I, II, III (...and its maturity level was way over my freakin' head... for reals) 7. Star Wars: Episode I: The Phantom Menace & Episode II: Attack of the Clones 8. X-Men (2000 Film) 9. Gone in 60 Seconds (Remake) 10. Lara Croft: Tomb Raider 11. Aliens (1986) 12. Mobile Suit Gundam Wing: Endless Waltz - [Recorded VHS - November 10th, 2000] (I watched it so much, my parents mock Wufei Chang's quote "I'm asking you are you guys doing the Right Thing!" all the time and tease me constantly about it. I rarely watch it anymore because of them ) 13. Xena: Warrior Princess - A Friend in Need (Directors Cut) 14. Kate and Leopold 15. Jurassic Park & The Lost World: Jurassic Park 16. Mad Max (I tried watching the other two, but I couldn't get into 'em.) 17. Digimon: The Movie 18. X2: X-Men United (when it was released) 19. Scooby Doo On Zombie Island/Scooby Doo's Greatest Mysteries (VHS) 20. Resident Evil Apocalypse (in 2005) 21. The Mummy (in 2007. Not by choice. My sister was always watching it whenever I was on the computer. >_<) 22. Disney Movies (too many to count) 23. Transformers: The Movie 24. War of the Worlds (2005 Film) 25. Sailor Moon R: The Promise of a Rose (VHS) 26. Sailor Moon S: Hearts in Ice (VHS) 27. Sailor Moon SuperS: Black Dream Hole (VHS) 28. Outlaw Star 29. Xena: Warrior Princess (Seasons I-VI) 30. Buffy: The Vampire Slayer (Season I-VII) 31. The Big O/The Big O II 32. Digimon Adventure/Digimon Adventure Zero Two 33. Yu-Gi-Oh! (The Original Series on KIDS WB!) ...Viola! All my Media Obessions.