Shanghai Surprise (1986)

Just one year after meeting and marrying Madonna, Sean Penn and The Material Girl herself teamed up for the mad dash comedy Shanghai Surprise in 1986. This crazy tale is about a sleazy con artist played by Penn who falls for a benevolent nurse played by Madonna. She's trying to secure some opium to help out her suffering patients, but is having trouble getting her hands on some. That's where Sean comes in. He has to fight off some dangerous baddies in order to get his hands on opium in the black market. We're Shanghai Surprised to see just how many times Sean Penn manages to get shirtless here. See his smooth sexy twenty-five year old bod in numerous shirtless scenes! This Penn will give you an inkblot in your boxers.