This list is more fluid for me, as my tastes and interests changed all the time. I will create several buckets:
Drama
1) Tombstone
2) Shawshank Redemption
3) The Usual Suspects
4) Donnie Brasco
5) The Hunt for Red October
6) Reservoir Dogs
7) Goodfellas
8) Gettysburg
9) Suicide Kings (Dennis Leary and the Toaster is one of the all time great monologues)
10) Boogie Nights
HM Glengarry Glen Ross, Lock Stock and Two Smoking Barrels, Saving Private Ryan
Comedy
1) Dirty Work
2) Mallrats
3) Dogma
4) PCU
5) Maverick
6) Major Payne
7) Office Space
8) Wayne's World
9) Robin Hood Men in Tights
10) Clerks
HM Lebowski, Half Baked, Meet Wally Sparks,
Sports
1) The Program
2) Tin Cup
3) The Sandlot
4) Kingpin
5) Major League II
6) Mr. Baseball
7) White Men Can't Jump
8) Happy Gilmore
9) The Waterboy
10) Varsity Blues
HM Major League Back to the Minors, Little Giants, Mystery Alaska, Ladybugs
Action
1) True Lies
2) Golden Eye
3) Terminator 2
4) Die Hard 2
5) The Professional
6) Point Break
7) The Matrix
8) Wild Wild West
9) US Marshals
Romantic Movies/Rom Coms
1) Swingers
2) Ten Things I Hate About You
3) Notting Hill
4) Something About Mary
5) Can't Hardly Wait
6) George of the Jungle
7) The Mask
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