Quicksand (1950)

Dan (Mickey Rooney) is a nice guy who needs $20 for a hot date with waitress Vera (Jeanne Cagney). He sneaks the sum from his boss, fully intending to pay it back later by collecting from a buddy who owes him. The friend never makes good on the money, so Dan pulls a small con for the cash. However, this petty crime lands Dan in hot water, and he finds himself committing a more serious transgression to buy his way out of trouble. But this is just the start of a very unlucky pattern.