1996

Brad Pitt

October

You're Money, Baby

Pitt scores a reported $17.5 million up front from Universal Pictures to star in the upcoming feature Meet Joe Black. It's his first mega-star-worthy paycheck after receiving $10 million for each of his previous two films.

1998

May

Not Just Friends

Pitt and Friends star Jennifer Aniston go on a first date brokered by their respective managers. While neither will reveal who asked for it, both seem pretty happy with the result. While they initially go out of their way not to be photographed together, the pair eventually admit that they are indeed a couple, with Pitt reluctantly telling Oprah Winfrey in October, "Uh, we met through friends."

1999

Brad Pitt

October 15

Box-Office Knockout

Pitt appears as Tyler Durden in the hyper-violent Fight Club. To fully get in shape for the role – a sleazy, leather-jacket-wearing waiter who runs an underground slugging joint – Pitt practiced boxing and tae kwon do for months. He also temporarily had caps pried off his front teeth and replaced with snaggles. "My girl likes them," he says to PEOPLE.

2000

Brad Pitt

July 29

I'll Be There for You

Among friends, fireworks and 50,000 flowers, Aniston and Pitt tie the knot on a Malibu bluff, reading marriage vows they composed themselves. Pitt promises to "split the difference on the thermostat" while Aniston pledges to always make his "favorite banana milkshake." Pitt's brother Doug, 33, serves as best man. Aniston chooses two bridesmaids: high school friend Andrea Bendewald, 30, and documentary filmmaker Kristin Hahn-Stringer, 31, one of the first friends Aniston made in L.A. Famous guests include Courteney Cox Arquette and husband David Arquette, Edward Norton, Salma Hayek and Melissa Etheridge.

Brad Pitt

November 13

We're Bringing Sexy Back

Pitt is the first man to be named PEOPLE's Sexiest Man Alive twice. "Brad was always gorgeous," says assistant managing editor Elizabeth Sporkin, who oversaw the issue, "but commitment has amped up his inner glow." Pal George Clooney joins him in the honor in 2006.

2001

March 02

Pretty Man...and Woman

Pitt appears in The Mexican with Julia Roberts, marking the first time the two A-list stars have ever shared the screen together. It won't be the last: they'll team up with George Clooney and Matt Damon later in the year for the remake of Ocean's Eleven.

Brad Pitt

November 22

The Famous Spouse

Playing a formerly dorky high school friend of David Schwimmer's character on Friends, guest star Pitt is invited to Thanksgiving dinner, where he squares off against Aniston's character, an old adversary. It is Pitt's only appearance on the show, although he is a frequent fixture on the set, often playing video games with Schwimmer or talking cars with Matt LeBlanc.

2003

Brad Pitt

March

Pitt Wears Short Skirts

Playing the ancient Greek warrior Achilles, Pitt begins filming Troy in a variety of locations, including Mexico and Malta. With production costs coming in around $185 million, it will be the most expensive picture Pitt has participated in, although it isn't the elaborate set that takes the most adjustment. "Let's just say that the skirt took a few weeks to get used to," he tells London's Sunday Times. "It's not even like a kilt. With a kilt, you've got a bit of length, but those Greeks liked the mini." Despite Pitt's overexposure, Troy will be a commercial disappointment when it premieres in May 2004, grossing $133 million domestically.

2004

Brad Pitt

January

Intrigue and Espionage

Shooting begins on the spy action movie Mr. & Mrs. Smith. It doesn't take long for the tabloids to print reports emerging from the set about real-life sparks between Pitt and the film's other title actor, Angelina Jolie. "We try as hard as we can just to stay away from [the gossip]," Aniston says in May. "We try to laugh, of course." Pitt's brother Doug tells PEOPLE, "It's crap. Total crap."

Brad Pitt

November

We Are the World

Pitt travels to South Africa to meet with former president Nelson Mandela and call attention to the country's AIDS epidemic before flying to Ethiopia on behalf of a Third World lobby group. "I've spent a wonderful week traveling this beautiful continent," he says in a statement, "listening to the people and learning about the AIDS crisis, the extreme poverty and what people in America can do to help." Continuing their work as social advocates, Pitt and Aniston lend their support to One Voice, a group promoting Middle East peace. Earlier in the year he campaigns for John Kerry and stem cell research.

Photo Credits

BIOGRAPHY (top to bottom): Everett; 20th Century FOX; Michael Sanville/Zuma; Danny Feld/AP; Warner Bros./Everett; Daniel Mayer; EPA/Landov

Name
Brad Pitt
Real Name
William Bradley Pitt
Date of Birth
December 18, 1963
Birth Place
Shawnee, Okla.
Relationships
Angelina Jolie, wife (2005 to present)
Jennifer Aniston, ex-wife (1998 to 2005)
Gwyneth Paltrow, ex-girlfriend
(1995 to 1997, engaged)
Jitka Pohlodek, ex-girlfriend (1993 to 1995)
Juliette Lewis, ex-girlfriend (1990 to 1993)
Robin Givens, ex-girlfriend (1989)
Jill Schoelen, ex-girlfriend (1988)
Children
Maddox Chivan, adopted son (8/5/01)
Pax Thien, adopted son (11/29/03)
Zahara Marley, adopted daughter (1/8/05)
Shiloh Nouvel, daughter (5/27/06)
Knox Leon, son (7/12/08)
Vivienne Marcheline, daughter (7/12/08)
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Edited by Julia Wang

Brad Pitt

Celebrity Central / Top 25 Celebs

 

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