01of 19Moonlighting, 1985ABC Photo Archives/Disney General Entertainment Content/GettyAfter starting out with smaller roles and theater work in N.Y.C., Bruce Willis entered the mainstream in 1985 in the seriesMoonlighting,alongside Cybill Shepherd. The dramedy about the pair’s private detective work lasted five seasons and earned Willis both an Emmy and Golden Globe Award.
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Moonlighting, 1985
ABC Photo Archives/Disney General Entertainment Content/Getty

After starting out with smaller roles and theater work in N.Y.C., Bruce Willis entered the mainstream in 1985 in the seriesMoonlighting,alongside Cybill Shepherd. The dramedy about the pair’s private detective work lasted five seasons and earned Willis both an Emmy and Golden Globe Award.
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Die Hard, 1988

Three years later, Willis pretty much cemented his place in pop culture in the iconic filmDie Hard,which has become perhaps the biggest piece of his on-camera legacy. Willis stars in the five-film series as New York City police detective John McClane — and in 2018 declared that the film is in factnota Christmas movie.Willis led the sequels, 1990’sDie Hard 2,1995’sDie Hard with a Vengeance, 2007’sLive Free or Die Hardand 2013’sA Good Day to Die Hard.
03of 19In Country, 1989Warner Bros/Kobal/ShutterstockIn 1990, Willis earned his fourth, most recent Golden Globe Award nomination for his role as Emmett Smith, a Vietnam veteran grappling with PTSD.
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In Country, 1989
Warner Bros/Kobal/Shutterstock

In 1990, Willis earned his fourth, most recent Golden Globe Award nomination for his role as Emmett Smith, a Vietnam veteran grappling with PTSD.
04of 19The Last Boy Scout, 1991Geffen Film Company/Kobal/ShutterstockDamon Wayans was Willis' costar in this buddy cop thriller that featured lots of explosions and has become a bit of a cult classic in the years since its release.
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The Last Boy Scout, 1991
Geffen Film Company/Kobal/Shutterstock

Damon Wayans was Willis' costar in this buddy cop thriller that featured lots of explosions and has become a bit of a cult classic in the years since its release.
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Death Becomes Her, 1992

In the early ’90s satire, Willis starred as Dr. Ernest Menville, object of Meryl Streep and rival Goldie Hawn’s affections.
06of 19Striking Distance, 1993Columbia/Kobal/ShutterstockWillis went the cop route again in this early ’90s thriller, which paired him with Sarah Jessica Parker. Through the years, he’s played opposite a whole bevy of talented leading ladies, including Halle Berry (Perfect Stranger), Sharon Stone (Alpha Dog) and even daughter Rumer Willis (Hostage).
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Striking Distance, 1993
Columbia/Kobal/Shutterstock

Willis went the cop route again in this early ’90s thriller, which paired him with Sarah Jessica Parker. Through the years, he’s played opposite a whole bevy of talented leading ladies, including Halle Berry (Perfect Stranger), Sharon Stone (Alpha Dog) and even daughter Rumer Willis (Hostage).
07of 19Pulp Fiction, 1994EverettWillis joined the all-star cast of the Quentin Tarantino classic as almost-past-his-prime boxer Butch Coolidge, taking a pay cut for the part but adding a new type of project to his résumé. He shared the screen with frequent collaborator Samuel L. Jackson, along with Uma Thurman and John Travolta.
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Pulp Fiction, 1994
Everett

Willis joined the all-star cast of the Quentin Tarantino classic as almost-past-his-prime boxer Butch Coolidge, taking a pay cut for the part but adding a new type of project to his résumé. He shared the screen with frequent collaborator Samuel L. Jackson, along with Uma Thurman and John Travolta.
08of 1912 Monkeys, 1995Polygram/Kobal/ShutterstockIn another celeb-heavy film, Willis played lead James Cole, a prisoner who time travels in an attempt to stop the release and spread of a deadly virus.
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12 Monkeys, 1995
Polygram/Kobal/Shutterstock

In another celeb-heavy film, Willis played lead James Cole, a prisoner who time travels in an attempt to stop the release and spread of a deadly virus.
09of 19The Fifth Element, 1997Columbia/Tri-Star/Kobal/ShutterstockWillis attempted to save humanity again in 1997 as Korben Dallas, alongside Milla Jovovich. “One of the things I remember is that [director Luc Besson] had for some reason dyed his hair blond. And I said, ‘You know what? I should dye my hair blond, have a little wig on my head.’ “Willis recalledto EW in 2017. “That was a contribution of mine, and he liked it.”
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The Fifth Element, 1997
Columbia/Tri-Star/Kobal/Shutterstock

Willis attempted to save humanity again in 1997 as Korben Dallas, alongside Milla Jovovich. “One of the things I remember is that [director Luc Besson] had for some reason dyed his hair blond. And I said, ‘You know what? I should dye my hair blond, have a little wig on my head.’ “Willis recalledto EW in 2017. “That was a contribution of mine, and he liked it.”
10of 19Armageddon, 1998Armageddon Cast.GettySure some found it cheesy, but the late-’90s blockbuster about a group of men sent to save Earth from a deadly asteroid made more than $500 million domestically — and Willis' role as selfless Harry Stamper left many a moviegoer in tears.
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Armageddon, 1998
Armageddon Cast.Getty

Sure some found it cheesy, but the late-’90s blockbuster about a group of men sent to save Earth from a deadly asteroid made more than $500 million domestically — and Willis' role as selfless Harry Stamper left many a moviegoer in tears.
11of 19The Sixth Sense, 1999Ron Phillips/Hollywood/Kobal/ShutterstockDo you see dead people? Willis' role as pscyhologist Malcolm Crowe came with one of the biggest twists of all time in the M. Night Shyamalan hit.
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The Sixth Sense, 1999
Ron Phillips/Hollywood/Kobal/Shutterstock

Do you see dead people? Willis' role as pscyhologist Malcolm Crowe came with one of the biggest twists of all time in the M. Night Shyamalan hit.
12of 19Friends, 2000Chris Haston/NBCWillis' three-episode stint as the father of Ross’s new girlfriend — and a brief love interest for Rachel — earned him his second Emmy Award.
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Friends, 2000
Chris Haston/NBC

Willis' three-episode stint as the father of Ross’s new girlfriend — and a brief love interest for Rachel — earned him his second Emmy Award.
13of 19The Whole Nine Yards, 2000Pierre Vinet/Morgan Creek/Kobal/ShutterstockThe actor got to have a little fun oppositeFriends’Matthew Perry as hitman Jimmy “the Tulip” Tudeski in this 2000 film.
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The Whole Nine Yards, 2000
Pierre Vinet/Morgan Creek/Kobal/Shutterstock

The actor got to have a little fun oppositeFriends’Matthew Perry as hitman Jimmy “the Tulip” Tudeski in this 2000 film.
14of 19Sin City, 2005Dimension Films/Kobal/ShutterstockWillis took a turn for the artsy when he joined the cast of Frank Miller and Robert Rodriguez’s dark drama as Detective John Hartigan.
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Sin City, 2005
Dimension Films/Kobal/Shutterstock

Willis took a turn for the artsy when he joined the cast of Frank Miller and Robert Rodriguez’s dark drama as Detective John Hartigan.
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Over the Hedge, 2006
VICTOR R. CAIVANO/AP

16of 19The Expendables 2, 2012EverettThe actor was anythingbutexpendable in the two-film franchise that costarred a serious slew of action stars including Sylvester Stallone, Jean-Claude Van Damme, Arnold Schwarzenegger and Jason Statham.
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The Expendables 2, 2012

The actor was anythingbutexpendable in the two-film franchise that costarred a serious slew of action stars including Sylvester Stallone, Jean-Claude Van Damme, Arnold Schwarzenegger and Jason Statham.
17of 19Moonrise Kingdom, 2012Indian Paintbrush/Kobal/ShutterstockWillis memorably joined the Wes Anderson family as Captain Sharp in the charming, quirky coming-of-age film that costarred Bill Murray, Edward Norton, Frances McDormand and Tilda Swinton.
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Moonrise Kingdom, 2012
Indian Paintbrush/Kobal/Shutterstock

Willis memorably joined the Wes Anderson family as Captain Sharp in the charming, quirky coming-of-age film that costarred Bill Murray, Edward Norton, Frances McDormand and Tilda Swinton.
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G.I. Joe: Retaliation, 2013
Paramount

19of 19Misery, 2015Joan Marcus/Polk and Co./APThe actor made a brief return to the stages of New York City alongside Laurie Metcalf in the Broadway adaptation of the Stephen King novel.
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Misery, 2015
Joan Marcus/Polk and Co./AP

The actor made a brief return to the stages of New York City alongside Laurie Metcalf in the Broadway adaptation of the Stephen King novel.
source: people.com