- 2009: Starred in the film, "Surrogates," which is based on the comic book of the same name
- 2007: Reprised role of John McClane in "Live Free or Die Hard," the fourth installment in the popular Die Hard action franchise
- 2007: Co-starred in Nick Cassavetes' "Alpha Dog," an independent feature about a real-life drug dealer
- 2006: Received a star on the Hollywood Walk of Fame (October)
- 2006: Starred as an infamous assassin, opposite Josh Hartnett, in the thriller "Lucky Number Slevin"
- 2005: Co-starred in "Sin City," an adaptation of Frank Miller's graphic novel; co-directed by Miller and Robert Rodriguez
- 2004: Reprised role as Jimmy 'The Tulip' Tudeski in "The Whole Ten Yards"
- 2003: Had lead in the action thriller, "Tears of the Sun," co-starring Cole Hauser and Monica Bellucci
- 2002: Was executive producer of "The Crocodile Hunter: Collision Course"
- 2002: Executive produced and starred in the Showtime adaptation of Sam Shepard's play "True West"
- 2002: Starred alongside Colin Farrell in "Hart's War"
- 2001: Co-starred with Billy Bob Thornton and Cate Blanchett in the comedy, "Bandits"
- 2000: Played Jimmy 'The Tulip' Tudeski, a hit man on the lam, in the comedy "The Whole Nine Yards"
- 2000: Made three-episode guest appearance on the NBC sitcom, "Friends," as a love interest for Rachel (Jennifer Aniston)
- 2000: With Arnold Rifkin, formed Cheyenne Enterprises
- 2000: Re-teamed with Shymalan for the film, "Unbreakable"
- 1999: Played Dwayne Hoover in Alan Rudolph's lackluster, "Breakfast of Champions"; Willis bankrolled project with brother David receiving producing credit
- 1999: Made uncredited guest appearance as a shrink on an episode of FOX's "Ally McBeal"
- 1999: Played the starring role in M. Night Shymalan's supernatural thriller, "The Sixth Sense"
- 1998: Played oil driller Harry Stamper in the Michael Bay-directed, "Armageddon"
- 1998: Portrayed US General William Devereaux in Edward Zwick's "The Siege"
- 1997: Starred in Luc Besson's sci-fi actioner "The Fifth Element"
- 1995: Played the lead role in Terry Gilliam's "Twelve Monkeys"
- 1995: Reprised his signature role of John McClane in the sequel "Die Hard With a Vengeance"
- 1994: Won critical praise for his supporting turns in Quentin Tarantino's "Pulp Fiction" and Robert Benton's "Nobody's Fool"
- 1994: Starred in and helped produce Richard Rush's disappointing "Color of Night"
- 1992: Appeared as himself in Robert Altman's "The Player"
- 1992: Cast against type as the milquetoast doctor in "Death Becomes Her"; stepped into role when Kevin Kline dropped out
- 1991: First screen credit as writer (provided story) for "Hudson Hawk"; also co-wrote "The Hudson Hawk Theme"
- 1991: Co-founded Planet Hollywood, along with actors Arnold Schwarzenegger and Sylvester Stallone
- 1991: First film with director Alan Rudolph, "Mortal Thoughts"; played a wife-beating bad guy; then-wife Demi Moore co-starred
- 1990: Again provided the voice of Mikey for the sequel, "Look Who's Talking Too"; also co-wrote the song "Daddy's Coming Home"
- 1990: Reprised role of McClane in "Die Hard 2: Die Harder"
- 1989: Won praise for his portrayal of a Vietnam veteran in Norman Jewison's "In Country"
- 1989: Voiced the thoughts of baby Mikey in the feature "Look Who's Talking"
- 1988: First film as producer, "Sunset"; also played the role of Tom Mix; second film with Edwards
- 1988: Breakthrough film role as John McClane in "Die Hard"
- 1987: Made feature film acting debut in Blake Edwards' "Blind Date"
- 1987: Headlined the HBO special, "Bruce Willis: The Return of Bruno"
- 1986: Released debut album, The Return of Bruno, which included the hit single "Respect Yourself"
- 1985: Debuted as a series regular, playing David Addison opposite Cybill Shepherd, in ABC's "Moonlighting" ; earned Golden Globe (1986, 1988) and Emmy (1986) nominations for Lead Actor in a Drama Series
- 1984: Breakthrough stage role, replaced Ed Harris, in the Off-Broadway production of Sam Shepard's "Fool for Love"
- 1980: Got a part in Dennis Watlington's play "Bullpen" and performed in it for four years in various venues
- 1980: First screen appearance, an uncredited walk-on, in "The First Deadly Sin"
- 1977: Made theater debut in the off-Broadway production of "Heaven and Earth"
- Formed Night Owl Promotions
- Worked as a bartender at NYC restaurants Chelsea Central and Cafe Central and the nightclub Kamikaze
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