I'm a huge movie buff, so fair warning.
Pootie Tang, Don't Be a Menace to South Central While Drinking Your Juice in the Hood, Undercover Brother, Stepbrothers, Young Frankenstien, The Goonies I used to watch religiously every freakin' weekend when I was a kid because I had it on Beta Max and my parents let me have the Beta Max player when I was 10.
Star Wars The Empire Strikes Back, Indiana Jones and the Temple of Doom, Friday the 13th Part 1-2-3, Night of the Living Dead, Eddie Murphy's Raw, The Golden Child, Time Bandits, the Adventures of Baron Munchhausen by Terry Gilliam, Monty Python and the Holy Grail (I'm estimating about 40-50 times), Blazing Saddles, Space Balls Tommy Boy, Happy Gilmore, Dumb & Dumber, Willow, Home Alone 1/2, Child's Play 1/2, Billy Madison (Stop laughing at me Swan), Shaun of the Dead, Hot Fuzz, Super Troopers (nearly 20 times now) Ace Ventura.
Mystery Science Theater 3000 movies such as: Santa Claus Conquers the Martians, Zombie Nightmare with Adam West, Manos the Hands of Fate, The Final Sacrifice, The Brain that Wouldn't Die, Overdrawn at the Memory Bank with Raul Julia, Space Mutiny, Time Travelers, and MITCHELL with Joe Don Baker.