Comedies
These movies are from the Comedy genre, from all generations.
1.  The Big Lebowski
2.  Caddyshack
3.  The Royal Tenenbaums
4.  Monty Python & The Holy Grail
5.  Fletch
6.  Dumb & Dumber
7.  Dogma
8.  Mister Roberts
9.  National Lampoons: Christmas Vacation
10. Austin Powers: International Man Of Mystery
11. South Park: Bigger Longer & Uncut
12. Ed Wood
13. Rushmore
14. O Brother Where Art Thou
15. 1941
16. The Apartment
17. Slap Shot
18. Support Your Local Sheriff
19. Ferris Bueller's Day Off
20. Philidelphia Story
21. When Harry Met Sally

Honorable Mention:  Old School, UHF, Tommy Boy, Office Space, Pootie Tang, Major League, Austin Powers 2, Austin Powers 3
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