In no particular order...
1. Ocean's Eleven- To be clear, I'm talking about the 2001 film directed by Steven Soderbergh and starring George Clooney and Brad Pitt and, like, a million other awesome actors. It tells the story of Danny Ocean and accomplices who aim to rob three Vegas casinos on the same night. It's super slick and very, very funny.
2. Sneakers- Released in 1992, directed by Phil Alden Robinson. Stars Robert Redford, Dan Ackroyd, Sydney Poitier, David Staratharin, and River Phoenix and more! This is the story a group of people whose job it is to break into places to test companies' security systems. But the past comes back to haunt the leader of the group and the gang must work together to pull off their biggest job yet.
3. Heat- Damn, this is an awesome movie. Released in 1995, written and directed by Michael Mann, and stars Al Pacino (cop) and Robert DeNiro (robber) in a very intense game of cat and mouse. And when I say 'intense', I really mean it.
4. The Italian Job- Again, I'm talking about the newer one. The one released in 2003 that stars Marky Mark. Sorry, Mark Walhberg. I know you're a legit actor now and all. This movie's about a crew that, after being betrayed and left for dead by one of their own, plans an elaborate gold heist. Every time I see this movie, I want to drive a mini cooper. And learn how to crack safes. Alas, I never done either.
5. Butch Cassidy and the Sundance Kid- This 1969 film was written by Princess Bride author William Goldman and directed by George Roy Hill. It stars Paul Newman (Butch) and Robert Redford (Sundance) as a pair of bank/train robbers who are forced to leave the country when the law gets too close for comfort. I adore this screenplay.