1) Princess Bride - Inconceivable I've seen this at least once a year for that past 15 years.
2) Fist of Legend - The gold standard of martial arts flicks; a remake of the Bruce Lee classic
3) Planes, Trains and Automobiles - Is it Thanksgiving yet?
4) Up - Broke the top 20 as soon as I saw it the first time
5) Collateral - I had to pick a Michael Mann so it was between this and Heat. Tom Cruise might bump this one off the list. Jamie Foxx helps.
6) Fast And The Furious - Tokyo - I wonder if you know, how they live in Tokyo
7) Fast Five - Love the cast, love the cars, who care about the plot
8) Thomas Crown Affair - What would you do for art?
9) G.I. Jane - The only Demi Moore movie I can watch more than once; a Ridley Scott classic
10) Ferris Bueller's Day Off - Inspiration to take the day off from work, any day
11) Pee Wee's Big Adventure - Tim Burton's best work and it's about a bike
12) Wall-E - First 15 minutes is the best 15 minutes of any animated movie. Spork.
13) Singles - Best Matt Dillon acting; it's all about the music
14) Finding Forrester - Hoops and literature and friendship; my fav Sean Connery movie
15) Blade Runner - I need a dark movie for my list so it had to be this one
16) The Matrix - either this Keanu or the Point Break Keanu. This one always gives me plenty to think about.
17) Idiocracy - The best comedy in the last 10 years. Smart, relatively speaking.
18) Contact - I always wonder if someday this movie will be classified as pseudo-fiction
19) Romeo Must Die - Hip hop meets kung fu; Jet Li, the late Aaliyah, DMX
20) Goldfinger - If I will see only one spy movie again, this is it. Love the 60s cars in this flick.