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Willis was originally cast as Terry Benedict in Ocean's Eleven (2001) but dropped out to work on recording an album.In Ocean's Twelve (2004), he makes a cameo appearance as himself.He filled in for an ill David Letterman on his show February 26, 2003, when he was supposed to be a guest.On many of his appearances on the show, Willis stages elaborate jokes, such as wearing a day-glo orange suit in honor of the Central Park gates, having one side of his face made up with simulated buckshot wounds after the Harry Whittington shooting, or trying to break a record (parody of David Blaine) of staying underwater for only twenty seconds.Willis also worked with his eldest daughter, Rumer, in the 2005 film Hostage.In 2007, he appeared in the thriller Perfect Stranger, opposite Halle Berry, the crime/drama film Alpha Dog, opposite Sharon Stone, and reprised his role as John Mc Clane in Live Free or Die Hard.This marked Willis's second collaboration with director Robert Rodriguez, following Sin City.Willis has appeared on the Late Show with David Letterman several times throughout his career.

However, due to the 2007 Writers Guild of America strike, the film was cancelled.That same year, he starred in Mike Judge's animated film Beavis and Butt-head Do America with his then-wife Demi Moore.In the movie, he plays a drunken criminal named "Muddy Grimes", who mistakenly sends Judge's titular characters to kill his wife, Dallas (voiced by Moore).He is known for his role of John Mc Clane in the film Die Hard film series (1988–2013).Willis has appeared in over 60 films, including Death Becomes Her (1992), Pulp Fiction (1994), 12 Monkeys (1995), The Fifth Element (1997), Armageddon (1998), The Sixth Sense (1999), Unbreakable (2000), Sin City (2005), Red (2010), Moonrise Kingdom (2012) The Expendables 2 (2012) and Looper (2012).

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