Win It All (2017)
Eddie Garrett agrees to watch a duffel bag for an acquaintance who is heading to prison. When he discovers cash in the bag, he's unable to resist the temptation and winds up deeply in debt. When the prison release is shortened, Eddie suddenly has a small window of time to win all the money back.
Director: Joe Swanberg
Writers: Jake Johnson, Joe Swanberg
Stars: Keegan-Michael Key, Jake Johnson, Joe Lo Truglio