Okay, here's an easy one:
Best Trading Comedy - Trading Places
This was a great movie on all counts. Dan Aykroyd and Eddie Murphy were perfect in their rolls. I still remember as a teenager watching the "OJ Pit" scene at the theater - well before my trading days - blown away at what was going on. It wasn't until several years later when I rented the video and watched the pit scene about a dozen times that I finally clued in to what they were doing (and I knew about short selling by that time!)
It's a lot of fun to watch and inspirational too. Makes you really want to think big when it comes to your trades, doesn't it?
Erich