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A couple of self-evident truths: Bruce Willis is one of the coolest men Hollywood has ever produced. There is a confidence and effortlessness to how he carries himself, how he dresses, and how he wears a baseball cap that makes other men look at Willis and think: I want to be like that guy. These photos from the last several decades demonstrate that effortless cool. The other aspect of Willis fueling this cool factor—and it's the other self-evident truth—is that he's appeared in some excellent movies, many of which have incredible repeat value. Die Hard. Pulp Fiction. Armageddon. 12 Monkeys. The Sixth Sense. Moonrise Kingdom. To name but a few. On March 30, 2022, Willis's daughter, Rumer, announced that her dad was suffering from aphasia, a condition affecting his cognitive abilities and that he would be stepping away from acting. It's a heartbreaking announcement, and we wish Willis all the good health in the world.
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Bob Riha Jr//Getty Images
Backstage at the Emmy Awards in L.A. on September 21, 1986.
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Ron Galella//Getty Images
Arriving at rehearsals for the '86 Emmy Awards.
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Jeff Kravitz//Getty Images
At the 1988 Democratic Celebrity Caravan in Los Angeles.
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Michael Ochs Archives//Getty Images
With this then-wife Demi Moore for the premiere of Chances Are in L.A. on March 8, 1989.
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Jim Smeal//Getty Images
At Bar One Nightclub in Beverly Hills on June 16, 1990.
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Jim Smeal//Getty Images
At China Club in Hollywood on June 26, 1990.
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Ron Galella, Ltd.//Getty Images
Walking into CNN Hollywood Studios for a taping of "Larry King Live" on May 17, 1991.
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Ron Galella//Getty Images
At the Carlyle Hotel in New York City on October 21, 1991.
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Mark Reinstein//Getty Images
Performing on stage at the grand opening of Planet Hollywood in Washington, DC, on October 3, 1993.
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Mark Reinstein//Getty Images
Same night, taking off (or putting on?) his pants.
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Lawrence Schwartzwald//Getty Images
On roller skates on Columbus Avenue in New York City on April 30, 1994.
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Stephane Cardinale - Corbis//Getty Images
At the Pulp Fiction party during the 47th Annual Cannes Film Festival in May 1994.
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Ron Galella, Ltd.//Getty Images
At the American Cinematheque Award Salute to Bruce Willis on September 23, 2000 in Beverly Hills.
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Bobby Bank//Getty Images
Exiting the Broadhurst Theatre in New York City on February 14, 2016.
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Rich Fury//Getty Images
At the Comedy Central Roast of Bruce Willis on July 14, 2018 in Los Angeles.