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Bruce Willis' first major film roles was in the 1987 Blake Edwards film Blind Date, with Kim Basinger and John Larroquette. Edwards cast him again to play the real-life cowboy actor Tom Mix in Sunset (1988). However, it was his then-unexpected turn in the film Die Hard (1988) that catapulted him to movie star status. He performed most of his own stunts in the film, and the film grossed $138,708,852 worldwide. Following his success with Die Hard, he had a supporting role in the drama In Country as Vietnam veteran Emmett Smith and also provided the voice for a talking baby in Look Who's Talking, as well as its sequel Look Who's Talking Too.
In the late 1980s, Bruce Willis enjoyed moderate success as a recording artist, recording an album of pop-blues titled The Return of Bruno, which included the hit single "Respect Yourself",promoted by a Spinal Tap-like rockumentary parody featuring scenes of him performing at famous events including Woodstock. Follow-up recordings were not as successful, though Bruce Willis has returned to the recording studio several times. See Discography below.
In 2000, Bruce Willis won an Emmy for Outstanding Guest Actor in a Comedy Series for his work on Friends (in which he played the father of Ross Geller's much-younger girlfriend). He was also nominated for a 2001 American Comedy Award (in the Funniest Male Guest Appearance in a TV Series category) for his work on Friends. Also in 2000, Bruce Willis played Jimmy "The Tulip" Tudeski in The Whole Nine Yards alongside Matthew Perry. 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. In 2007, he appeared in the Planet Terror half of the double feature Grindhouse as the villain, a mutant soldier. This marks Willis's second collaboration with director Robert Rodriguez, following Sin City.
Bruce Willis has appeared on The Late Show with David Letterman several times throughout his career. 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, Bruce 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.
On April 12, 2007, Bruce Willis appeared again, this time wearing a Sanjaya Malakar wig. His most recent appearance was on June 25, 2007 when he appeared wearing a mini-turbine strapped to his head to accompany a joke about his own fictional documentary titled An Unappealing Hunch (a wordplay of An Inconvenient Truth). Bruce Willis also appeared on Japanese Subaru Legacy television commercials. Tying in with this, Subaru did a limited run of Legacys, badged "Subaru Legacy Touring Bruce", in honor of Willis.
Bruce Willis has appeared in four films with Samuel L. Jackson (National Lampoon's Loaded Weapon 1, Pulp Fiction, Die Hard with a Vengeance, and Unbreakable) and both actors were slated to work together in Black Water Transit, before dropping out. Bruce 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 marked his return to the role of John McClane in Live Free or Die Hard. Recently he appeared in the films What Just Happened and Surrogates, based on the comic book of the same name.
Bruce Willis was slated to play U.S. Army general William R. Peers in director Oliver Stone's Pinkville, a drama about the investigation of the 1968 My Lai Massacre. However, due to the 2007 Writers Guild of America strike, the film was cancelled. Willis appeared on the 2008 Blues Traveler album North Hollywood Shootout, giving a spoken word performance over an instrumental blues-rock jam on the track "Free Willis (Ruminations from Behind Uncle Bob's Machine Shop)". In early 2009, he appeared in an advertising campaign to publicize the insurance company Norwich Union's change of name to Aviva.
Bruce Willis starred with Tracy Morgan in the comedy Cop Out, directed by Kevin Smith and about two police detectives investigating the theft of a baseball card. The film was released in February 2010. Willis appeared in the music video for the song "Stylo" by Gorillaz. Also in 2010, he appeared in a cameo with former Planet Hollywood co-owners and '80s action stars Sylvester Stallone and Arnold Schwarzenegger in the film The Expendables.
Bruce Willis played the role of "Mr. Church". This was the first time these three legendary action stars appeared on screen together. Although the scene featuring the three was short, it was one of the most highly anticipated scenes in the film. The trio filmed their scene in an empty church on October 24, 2009. His most recent project was Red, an adaptation of the comic book mini-series of the same name, in which he portrayed Frank Moses. The film was released on October 15, 2010.
On October 12, 2011, it was announced that A Good Day to Die Hard would see a February 14, 2013 (Valentine's Day) release, with Bruce Willis reprising his most famous role of John McClane for a fifth time.
