23. Shanghai Surprise (1986)
Director: Jim Goddard
Stars: Sean Penn, Madonna, Paul Freeman, Richard Griffiths
Lame Love Song: "Breath Away From Heaven," George Harrison
Love Conquers: Chinese Organized Crime
You are probably shocked to hear that Sean Penn and Madonna didn't exactly light up the screen together, even though they were newlyweds at the time. Things were far more exciting off-screen, as Penn landed in jail the year of film's release for assaulting a friend of Madonna's and attacking an extra on the set of At Close Range.
Though Sean Penn and Madonna didn't make it in the end, they were lucky enough to go on to have a number of destructive Hollywood relationships damaging the personal and professional lives of those involved.