Entertainment Movies Bruce Willis's Career in Photos A look back at the beloved actor's successful career By Kate Hogan Updated on July 15, 2022 11:20 AM Share Tweet Pin Email Trending Videos 01 of 19 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 series Moonlighting, 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. 02 of 19 Die Hard, 1988 Moviestore/Shutterstock Three years later, Willis pretty much cemented his place in pop culture in the iconic film Die 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 fact not a Christmas movie. Willis led the sequels, 1990's Die Hard 2, 1995's Die Hard with a Vengeance, 2007's Live Free or Die Hard and 2013's A Good Day to Die Hard. 03 of 19 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. 04 of 19 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. 05 of 19 Death Becomes Her, 1992 Moviestore/Shutterstock In the early '90s satire, Willis starred as Dr. Ernest Menville, object of Meryl Streep and rival Goldie Hawn's affections. 06 of 19 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). 07 of 19 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. 08 of 19 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. 09 of 19 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 recalled to EW in 2017. "That was a contribution of mine, and he liked it." 10 of 19 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. 11 of 19 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. 12 of 19 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. 13 of 19 The Whole Nine Yards, 2000 Pierre Vinet/Morgan Creek/Kobal/Shutterstock The actor got to have a little fun opposite Friends' Matthew Perry as hitman Jimmy "the Tulip" Tudeski in this 2000 film. 14 of 19 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. 15 of 19 Over the Hedge, 2006 VICTOR R. CAIVANO/AP The actor has actually done quite a bit of voicework throught his career, including in this Dreamworks film that raked in more than $300 million. You can also hear him in Look Who's Talking, The Lego Movie 2 and Bruno the Kid, among other TV shows and movies. 16 of 19 The Expendables 2, 2012 Everett The actor was anything but expendable 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. 17 of 19 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. 18 of 19 G.I. Joe: Retaliation, 2013 Paramount Willis kept his action-star status up with this film, based on the TV show and characters of the '80s and '90s and costarring Dwayne "The Rock" Johnson and Adrienne Padalecki. 19 of 19 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.