Three amateurs stickup a Mob protected card game, causing the local criminal economy to collapse. Brad Pitt plays the hitman hired to track them down and restore order. Killing Them Softly also features Richard Jenkins , James Gandolfini, Ray Liotta, Scoot McNairy, Ben Mendelsohn, and Vincent Curatola. Max Casella, Trevor Long, Slaine and Sam Shepard also make appearances.

Jack is a shy and awkward man who drives a limo and lives an unassuming life. His friend and co-worker, Clyde, and his wife Lucy, feel sorry for Jack and set him up on a blind date with Connie. Connie shares Jack's shyness and awkwardness, but through each other they seem to be able to find solace within themselves. Trouble might be brewing in paradise though, as Clyde and Lucy's marriage stumbles just as Jack and Connie's relationship grows.