2000

Bruce Willis

April 27

He'll Be There for You

Willis plays the father of Ross' (David Schwimmer) 20-year-old girlfriend in three episodes of the sitcom Friends. Matthew Perry suggests Willis, his costar in The Whole Nine Yards, for the part. Willis donates his Friends paycheck to several charities, and kisses Jennifer Aniston in one scene.

2001

June 29

Off Off Off Off Broadway

On the stage of the 250-seat Liberty Theater in Hailey, Idaho, Willis – who cofounded the small theater company in his adopted hometown – performs in the Sam Shepard drama True West. His debut performance, which takes place just three days after his 42-year-old brother Robert's death from cancer, is attended by Moore and her boyfriend, Oliver Whitcomb, as well as his daughter Scout, 9, who presents Dad with a bouquet of roses after the show.

2003

February 26

Here's Bruce!

"This has always been my dream," says comic Brian Kiley on CBS's Late Show, "to be on The Bruce Willis Show." Willis, who is supposed to be on as a guest, gets roped into hosting after David Letterman comes down with an eye infection. He holds his own, interviewing CBS news anchor Dan Rather about his exclusive interview with Saddam Hussein and welcoming Kiley, Carmen Electra and musical guest John Mayer.

Bruce Willis

June 18

All in the Family

Willis parties with Demi Moore, her beau Ashton Kutcher, and their daughters at the premiere of Charlie's Angels: Full Throttle. At the afterparty, Willis sits near Moore while she perches herself on Kutcher's lap. "I liked Ashton right away," Willis tells PEOPLE. "We just kind of hit it off. For me, as long as she's happy, I know the kids are going to be happy."

Bruce Willis

September

Burning Hot

Moore isn't the only one to find a younger playmate. After several movie dates with kids and popcorn at each other's houses, Willis and Brooke Burns, the 25-year-old host of the NBC reality show Dog Eat Dog head to Costa Rica, where she's shooting the movie Death to Supermodels. The pair – who date until May 2004 – hit a slew of hot spot destinations from Paris to Vegas during their whirlwind romance. But with Willis' schedule and Burns filming her television series North Shore in Hawaii, the distance proves too much for the relationship to overcome.

2005

Bruce Willis

March 11

Scary Scenario

In Hostage, Willis plays a former hostage negotiator, rescuing his kidnapped daughter, played by real-life daughter Rumer. "I was just physically and emotionally drained at the end of that night," Willis tells PEOPLE about filming the scene where she's tied up and crying for help. "Actors sometimes have to go to horrible places. Just imaging having one of my children held hostage is my worst nightmare."

2006

Bruce Willis

September 23

Action Resurrection

Willis begins filming the fourth installment of his Die Hard franchise, Live Free or Die Hard, with Justin Long (right). This time around, his John McClane character saves the country from computer-geek terrorists, but director Len Wiseman keeps Willis in classic brawling mode.

2007

April

Bruce's Busy Spring

Willis celebrates his 52nd birthday before the release of two new films. In the Quentin Tarantino-Robert Rodriguez double feature Grindhouse, Willis plays gun-totting Lt. Muldoon, and he stars opposite Halle Berry in the cat-and-mouse thriller Perfect Stranger.

Bruce Willis

June

Vanity Fair's Coverboy

Willis, 52, appears on the cover of Vanity Fair's June issue, in which he discusses his bond with ex-wife Demi Moore, 44, and her husband Ashton Kutcher, 29. "Demi is the mother of my children and Ashton is the stepfather of my children," he says (Willis and Moore have daughters Rumer, 18; Scout, 15; and Tallulah, 13). "I'm thrilled that Ashton turned out to be such a great guy. I love Demi, and I know she loves me." Next up for the action star: the highly-anticipated sequel, Live Free or Die Hard, slated for June 27.

Photo Credits

BIOGRAPHY (top to bottom): Everett Collection; Kevin Winter/Getty; Carlo Allegri/Getty; Miramax/Everett; Twentieth Centuy Fox; Courtesy Vanity Fair Magazine

Edited by Mai Dinh, Janet Murphy