The Asphalt Jungle (1950) / The Killing (1956).
It's impossible to separate these two terrific heist flicks, both of which largely set the template for every similar picture to follow over the years. Both are directed by legendary directors (John Huston on Jungle, Stanley Kubrick on Killing), both star gravel-voiced Sterling Hayden (who could easily have handled Nick Nolte's Good Thief role) as the soft-hearted criminal who doesn't quite get away with it, both feature superb supporting casts (Marilyn Monroe has one of her earliest roles in Jungle, while Killing features Elisha Cook Jr. as the final word in screen patsies), and both still have the power to hold audiences captive to this day.
Long considered a model of its kind, French writer-director Jules Dassin's absorbing drama employs the three-act structure that works well for any film of this nature: the meticulous planning of the robbery, the crime itself, and the aftermath during which things begin to unravel for the crooks involved. Jean Servais gives an appropriately lived-in performance as the world-weary (and world-wary) leader of the pack, while Dassin himself (billed under the pseudonym Perlo Vita) plays Cesar, the team member whose eye for the pretty ladies leads to the group's downfall. The robbery sequence, dialogue-free for its entire duration (roughly a half-hour), is justifiably famous among cineasts.
The Great St. Louis Bank Robbery (1959).
In the year sandwiched between the releases of The Blob (1958) and The Magnificent Seven (1960), Steve McQueen starred in this largely forgotten but still worthwhile caper yarn. McQueen plays a dissatisfied loner who teams up with three veteran crooks to rob a bank. The plan looks perfect on paper, but all hell breaks loose once the quartet storm the building. Filmed on the cheap, this is nevertheless a well-paced drama that scores further points for attempting to add a psychological slant to the proceedings (one criminal's hatred of women can be traced to his rocky relationship with his mom, while another suffers from bouts of claustrophobia triggered by his memories of life behind bars). Based on a true story; in fact, the policemen in the film are played by the real-life cops who took part in the apprehension of the bank robbers.
The Thomas Crown Affair (1999).
A badly dated caper film/love story, 1968's The Thomas Crown Affair is one of those all-glitz-no-substance throwaways that were so popular in the 50s and 60s. Even its selling points -- a steamy chess game played between stars Steve McQueen and Faye Dunaway, and the Oscar-winning song "The Windmills of Your Mind" -- seem laughable today. Here, then, is that cinematic rarity: a remake that improves on the original. Mining the same basic storyline but adding a handful of alterations in both story content and characterization, this new Affair finds Pierce Brosnan taking over the miscast McQueen's title role, a millionaire who's so bored with his lot in life that he challenges himself by successfully planning and pulling off a robbery. Nobody suspects this influential businessman of being a criminal mastermind except for an insurance company investigator (Rene Russo) who falls for the dapper gent even as she tries to bring him to justice. A mellow movie for grownups, this features some clever plot twists and good performances by Brosnan and especially Russo.