Gigli

This gangster rom-com bombed at the US box office, and currently has the dubious honour of being the worst movie in the Internet Movie Database. The titular Gigli, a gangster, is ordered to kidnap the mentally-retarded brother of a prosecutor, to give his boss some leverage in court. The boss, not trusting Gigli, sends a female (lesbian) gangster to keep him company. Naturally boy meets girl and one thing leads to another...