There's a slew of great character pieces that revolve around heists, robberies or drug dealing that go awry, such as Dog Day Afternoon, Heat, The Great Escape, Catch me if you Can, and then there are just straight satisfying adventures that deliver the "Big Con".
the 1973 classic caper film set in the depression era involving two professional grifters (Paul Newman and Robert Redford) setting up "the big con" to take mob boss (Robert Shaw). Inspired by real-life stories in David Maurer's book "The Big Con: The story of the Confidence Man". With beautiful title cards sub dividing the story, David S. Ward has set the tone for many other films that have followed in his footsteps (Ocean's 11 and Snatch).
The Italian Job (2003 or 1969)
Recent remakes of classics (ie. Thomas Crown Affair) always seem to shine a bit too brightly, maybe it's the dulling down of the main characters that are a bit rough around the edges. Both films are entertaining of course, but the 1969 version starring Michael Caine has a bit less pomp and more punch. The 2003 commercial release, starring Mark Wahlberg, Charlize Theron and Edward Norton looks a bit like a mini car ad, featuring some slick action sequences.
The Thomas Crown Affair (1968)
Norman Jewison's scintillating heist flick that spawned a remake (possible sequel to that), starring the infallible Steve McQueen and Faye Dunaway in this sizzling combustion of cat and mouse.