1980s: Moonlighting, Die Hard and rise to fame in 1989 Willis was cast as David Addison Jr. in the television series
Moonlighting (1985–1989), competing against 3,000 other actors for the position. His starring role in
Moonlighting, opposite
Cybill Shepherd, helped to establish him as a comedic actor. During the show's five seasons, he won an
Emmy Award for Outstanding Lead Actor in a Drama Series and a
Golden Globe Award for Best Actor – Television Series Musical or Comedy. The advertising campaign paid Willis US$5–7 million over two years. Willis chose not to renew his contract when he decided to stop drinking alcohol in 1988. In 1987, Willis obtained his first lead role in the
Blake Edwards film
Blind Date, co-starring with
Kim Basinger and
John Larroquette. and the film grossed $138,708,852 worldwide. Following his success with
Die Hard, Willis 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 (1989) and the sequel Look Who's Talking Too'' (1990). In the late 1980s, Willis enjoyed moderate success as a
recording artist, recording an album of pop-blues,
The Return of Bruno, credited to Willis's fictional
alter ego, Bruno Radolini, supposedly an influential blues musician. The album included the hit single "
Respect Yourself" using
the Pointer Sisters as guest vocalists. The LP was promoted by a
mockumentary featuring scenes of "Bruno" performing at famous events including
Woodstock. Willis released a version of
the Drifters song "
Under the Boardwalk" as a second single; it reached No. 2 on the
UK Singles Chart, but was less successful in the US. Willis returned to the recording studio several times.
1990s: Die Hard sequels, Pulp Fiction and dramatic roles 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). and propelled Willis to the first rank of Hollywood action stars. At one point,
Die Hard 2 and
Ghost, starring Willis's then wife
Demi Moore, would occupy the number one and number two spots at the box office, a feat that would not be accomplished again for a married Hollywood couple until 2024. In the early 1990s, Willis's career suffered a moderate slump, as he starred in
flops such as
The Bonfire of the Vanities (1990) and
Hudson Hawk (1991), although he did find box office success with
The Last Boy Scout (1991). He gained more success with
Striking Distance (1993) but flopped again with
Color of Night (1994): 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.
Maxim also ranked his sex scene in the film as the best in film history. In 1994, Willis also had a leading role in one part of
Quentin Tarantino's acclaimed
Pulp Fiction; 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),
The Fifth Element (1997) and
The Jackal (1997), the latter of which was a box-office success despite negative reviews. These were followed by
Mercury Rising (1998) and
Breakfast of Champions (1999), which were also poorly reviewed. In 1998 his voice and likeness were featured in the
PlayStation video game
Apocalypse. Willis was involved in
Broadway Brawler as both producer and lead actor. That production failed, and as compensation he was contracted for three films:
Armageddon,
The Sixth Sense and ''
Disney's The Kid. Both Armageddon
and The Sixth Sense'' were critical and commercial successes, with the former being the highest-grossing film of 1998 worldwide.
2000s '' In 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
Friends star
Matthew Perry, and Russ Duritz in ''
Disney's The Kid opposite Emily Mortimer. 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 2006, he lent his voice as RJ the Raccoon in Over the Hedge. 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 the director
Robert Rodriguez, following
Sin City. Willis appeared on the
Late Show with David Letterman several times throughout his career. He filled in for an ill
David Letterman on his show on February 26, 2003, when he was supposed to be a guest. On many of his appearances on the show, Willis staged 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
birdshot wounds after the
Harry Whittington shooting, or trying to break a record (a 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-wind turbine 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 (1993's National Lampoon's
Loaded Weapon 1, 1994's
Pulp Fiction, 1995's
Die Hard with a Vengeance, 2000's
Unbreakable, and 2019's
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 2006, he appeared in the crime/drama film
Alpha Dog, opposite
Sharon Stone. In 2007, he appeared in the
thriller Perfect Stranger, opposite
Halle Berry, and reprised his role as
John McClane in
Live Free or Die Hard. Subsequently, he appeared in the films
What Just Happened (2008) and
Surrogates (2009), 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 canceled. 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.
2010s '' co-star
Sylvester Stallone As of 2010, Willis was the eighth highest-grossing actor in a leading role and 12th-highest including supporting roles. Willis starred with
Tracy Morgan in the 2010 comedy
Cop Out, directed by
Kevin Smith, about two police detectives investigating the theft of a baseball card. Willis appeared in the music video for the song "
Stylo" by
Gorillaz. Also in 2010, he appeared in a cameo with the former
Planet Hollywood co-owners and 80s action stars
Sylvester Stallone and
Arnold Schwarzenegger in the film
The Expendables. Willis played the role of CIA agent "
Mr. Church". It was the first time the three action stars had 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. Willis next starred in
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. Willis starred alongside
Bill Murray,
Edward Norton, and
Frances McDormand in
Moonrise Kingdom (2012). Filming took place in
Rhode Island under the direction of
Wes Anderson, in 2011. Willis returned, in an expanded role, in
The Expendables 2 (2012). He appeared alongside
Joseph Gordon-Levitt in the sci-fi action film
Looper (2012), as the older version of Gordon-Levitt's character, Joe. Willis teamed up with
50 Cent in a film directed by
David Barrett called
Fire with Fire, starring opposite
Josh Duhamel and
Rosario Dawson, about a fireman who must save the love of his life. Willis also joined
Vince Vaughn and
Catherine Zeta-Jones in
Lay the Favorite, directed by
Stephen Frears, about a Las Vegas cocktail waitress who becomes an elite professional gambler. The two films were distributed by
Lionsgate Entertainment. Willis reprised his most famous role, John McClane, for a fifth time, starring in
A Good Day to Die Hard, which was released on February 14, 2013. In an interview, Willis said, "I have a warm spot in my heart for
Die Hard..... it's just the sheer novelty of being able to play the same character over 25 years and still be asked back is fun. It's much more challenging to have to do a film again and try to compete with myself, which is what I do in
Die Hard. I try to improve my work every time." That same year, Willis reprised his role as Frank Moses in
Red 2. On October 12, 2013, Willis hosted
Saturday Night Live with
Katy Perry as a musical guest. In 2015, Willis made his
Broadway debut in
William Goldman's adaptation of
Stephen King's novel
Misery opposite
Laurie Metcalf at the
Broadhurst Theatre. His performance was generally panned by critics, who called it "vacant" and "inert". Willis was the subject of a
roast by
Comedy Central in a program broadcast on July 29, 2018. Willis played himself in a cameo in the 2019 film
The Lego Movie 2: The Second Part.
2020s: Critical decline, health problems and retirement In the final years of his career, Willis starred in many low-budget
independent thrillers and science fiction films. Most of the films were released
direct-to-video and were widely panned.
Chris Nashawaty of
Esquire described the direct-to-video films as "a profitable safe harbor" for older actors, similar to
The Expendables. Willis would often earn US$2 million for two days' work, with an average of 15 minutes' screentime per film. He nonetheless featured heavily in the films' promotional materials, earning them the derogatory nickname "
geezer teasers". Those working on the films later said Willis appeared confused, did not understand why he was there and had to be fed lines through an
earpiece. The Golden Raspberry Awards retracted its Willis category, deeming it inappropriate to give a Razzie to someone whose performance was affected by a medical condition. At the time of his retirement, Willis had completed 11 films awaiting release. ==Business activities==