The Italian Job (1969) -- Michael Caine leads a crew of Brits through the streets of Turin to pull off a heist during the World Cup celebrations. Don't be hoodwinked into renting the re-make; it's a pale imitation that lacks all the imagination and cool of the original.
Shallow Grave (1994) -- Ewan McGregor, Christopher Eccleston and Kerry Fox are roommates who share a very dark sense of humour. When they find a dead body and a lot of money their friendship may be at risk. This film is very dark, and more than a little violent but also very funny.
The Prestige (2006) -- Michael Caine again, here with Christian Bale and Hugh Jackman in a tale about two rival magicians. Before I saw this film, someone told me to pay close attention to a certain scene because it would reveal the ending. I paid attention and still gasped as the ending played out screen.
The Spanish Prisoner (1997) -- Campbell Scott and Steve Martin headline this clever con film. Maybe my favourite David Mamet film, the script is filled with sharp dialog and plot twists right to the last lines.
Knowing (2009) -- Strange things start to happen after a time capsule is opened; Nicholas Cage leads. Probably the cheeziest movie on this list but I really appreciated the follow-through.
War of the Roses (1989) -- When Michael Douglas and and Kathleen Turner decide to get a divorce, it gets ugly, fast. Another black comedy, the details in the final scene paint it even darker.
The Talented Mr. Ripley (1999) -- Matt Damon finds that he is skilled in impersonation while on a trip to Italy to retrieve a playboy living in luxury. At once dreamlike and creepy, this film will stick in your mind.