Willis had his first lead role in a feature film 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) as John McClane that catapulted him to movie star and action hero 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 leading 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, 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" featuring The Pointer Sisters. The LP was promoted by a Spinal Tap–like rockumentary parody featuring scenes of Willis performing at famous events including Woodstock. He released a version of the Drifters song "Under the Boardwalk" as a second single; it got to No. 2 in the UK Top 40 but was less successful in the U.S. Willis returned to the recording studio several times afterward.
Having acquired major personal success and pop culture influence playing John McClane in Die Hard, Willis reprised his role in the sequels Die Hard 2 (1990) and Die Hard with a Vengeance (1995). These first three installments in the Die Hard series grossed over US$700 million internationally and propelled Willis to the first rank of Hollywood action stars.
In the early 1990s, Willis's career suffered a moderate slump, as he starred in flops such as The Bonfire of the Vanities (1990). He gained more success with Striking Distance (1993) but flopped again with Color of Night (1994): another box office failure, it was savaged by critics but did well in the home video market and became one of the Top 20 most-rented films in the United States in 1995.
In 1994, he had a supporting role as Butch Coolidge in Quentin Tarantino's acclaimed Pulp Fiction, which gave a new boost to his career. In 1996, he was the executive producer and star of the cartoon Bruno the Kid which featured a CGI representation of himself. 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 then played the lead roles in 12 Monkeys (1995) and The Fifth Element (1997). However, by the end of the 1990s his career had fallen into another slump with critically panned films like The Jackal, Mercury Rising, and Breakfast of Champions, saved only by the success of the Michael Bay-directed Armageddon which was the highest-grossing film of 1998 worldwide. The same year his voice and likeness were featured in the PlayStation video game Apocalypse. In 1999, Willis then played the starring role in M. Night Shyamalan's film, The Sixth Sense, which was both a commercial and critical success
n 2000, 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, 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 the sequel, Ocean's Twelve (2004), he makes a cameo appearance as himself. In 2005, he appeared in the film adaptation of Sin City. In 2007, he appeared in the Planet Terror half of the double feature Grindhouse as the villain, a mutant soldier. 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. 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.
On April 12, 2007, he appeared again, this time wearing a Sanjaya Malakar wig. On his June 25, 2007, appearance, he wore a mini-turban on his head to
accompany a joke about his own fictional documentary titled An Unappealing Hunch (a wordplay on An Inconvenient Truth). Willis also appeared in 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.
Willis has appeared in five films with Samuel L. Jackson (National Lampoon's Loaded Weapon 1, Pulp Fiction, Die Hard with a Vengeance, Unbreakable, and Glass) and both actors were slated to work together in Black Water Transit, before dropping out. 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 McClane in Live Free or Die Hard. Subsequently, he appeared in the films What Just Happened and Surrogates, based on the comic book of the same name.
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.