Madonna & Sean Penn, Shanghai Surprise (1986)
The Material Girl and Hollywood's bad boy met and married in a whirlwind 1985 romance triggered, indeed, on the set of her music video for ''Material Girl.'' The next year, they costarred in Shanghai Surprise, which bombed at the box office and was nominated for six Razzie Awards (with Madonna winning for Worst Actress). In the movie, Madonna played a 1930s medical missionary who seeks Penn's help in locating a stash of opium.
Box Office: A paltry $2.3 million
Relationship Longevity: The marriage lasted perhaps longer than it should have, finally dissolving in 1989. In an intriguing twist, Madonna called Penn the true love of her life in the 1991 documentary Truth or Dare. This probably came as a surprise to Madonna's then-boyfriend Warren Beatty, whom she met on the set of 1990's Dick Tracy. She also starred in another box office disaster, 2002's Swept Away, directed by her then-husband Guy Richie. Suffice it to say, showmances have not been good to Madonna.
—Darren Franich
Image Credit: Everett Collection
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