I’m sure I haven’t seen nearly as many movies as most folks, so most of my choices are pretty obvious mainstream ones. I’d go with:
1. The Big Lebowski — easy #1 for me
2. Swingers — I find this to be a good pick-me-up movie if I’m feeling down, and it’s a quick watch at around 90 minutes or so
3. The Bourne Identity
4. The Bourne Ultimatum
5. The Dark Knight
6. Wolf of Wall Street
7. Caddyshack
8. Good Will Hunting
9. Rounders
10. The Departed
If I could cheat and have a DVD that’s not a movie, the Pearl Jam - Live from New York City (MSG - 7/8/03) DVD has gotten a ton of play over the years.
Honorable mention: Boondock Saints, GoodFellas, Once Upon a Time in Hollywood, Ocean’s Eleven, Old School, Pirates of the Caribbean: The Curse of the Black Pearl, Joker, The Bourne Supremacy
It’s true, it’s true. Trust me …