Famous Celebrities and Their Daring R-Rated Movie Debuts

Matt Damon

Damon also made his R-rated film debut in Mystic Pizza alongside Julia Roberts in 1998. Damon was only 17 at the time of filming. He plays the role of Roberts’ rich new boyfriend’s younger brother.

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The More You Know

  • Peter O’Toole was nominated for eight performance Oscars and didn’t win a single one.
  • While filming Wall Street: Money Never Sleeps, Shia LaBeouf invested $20,000 in the stock market and ended up making more than $400,000.
  • For 'Fight Club' (1999), Brad Pitt had pieces of his front teeth chipped off to play Tyler Durden. He also took soap-making classes, boxing, taekwondo, and grappling lessons with Edward Norton to prepare for the role.
  • "Psycho" was the first time a flushing toilet was shown on screen.
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