Welcome to Collinwood (2002)

Synopsis
A group of likable losers try to pull of what by their standards seems like a major heist in this offbeat crime comedy, loosely based on the classic Italian caper comedy I Soliti Ignoti. A group of sad sacks living in a rundown neighborhood in Cleveland all have one thing in common -- they need money, and aren't especially fussy about how they get it. Riley (William H. Macy) is a guy whose wife has been sent to jail, leaving him to look after their baby, when she's unable to pay a fine. Pero (Sam Rockwell) is in love with a beautiful girl (Jennifer Esposito) who has a roving eye, and he's convinced that a bigger bankroll would help him win her heart. Leon (Isaiah Washington) is a hipster who wants to keep his sister, Michelle (Gabrielle Union), out of trouble. Basil (Andrew Davoli) is a guy with bad luck, and eyes for Michelle. And Toto (Michael Jeter) is a small-time crook looking for something to do -- if it's profitable, all the better. Someone gets the bright idea that a robbery might be the answer to everyone's problems, and with the help of Jerzy (George Clooney), a safe-cracker confined to a wheelchair, they set out to find the right target. Welcome to Collinwood was the first feature film from the writing and directing team of Anthony Russo and Joe Russo; filmmaker Steven Soderbergh and co-star George Clooney served as producers. ~ Mark Deming, All Movie Guide