John Huston's The Ashphalt Jungle (1950)
I saw this two decades ago, during a John Huston retro. And I was blown. It's a film about racketeers. Every character made an emotional connect with me. Even the villain's death is poignant.
AJ makes you feel sad about people you won't even know existed. Great writing. Great cinema. Shot in stunning black and white, AJ is the granddaddy of all caper thrillers, and influenced almost every film listed here. Louis Calhern, the 'gaddaar' in AJ sums it best: 'After all, crime is only a left-handed form of human endeavour.'
AJ features a great ensemble cast. Amongst others, it has a sterling performance from Sterling Hayden (who also starred in The Godfather -- guess who he played?) The film also introduces a nubile actress who became a legend and icon: Marilyn Monroe.
Watch Johnny Gaddaar to see what I stole from this classic.
Also read: The Gaddaars of Bollywood