- 1996


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
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


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


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.


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
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.


The Famous Husband
Playing a formerly dorky high school friend of Courteney Cox Arquette'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 David Schwimmer or talking cars with Matt LeBlanc.
- 2003
Trouble Signs?
Aniston forgets to thank Pitt during her acceptance speech for best actress in a TV comedy at the Golden Globes, prompting speculation that there may be a few cracks in their marriage.


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 Australia'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


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."
Photo Credits
BIOGRAPHY (top to bottom): Everett; 20th Century Fox; Michael Sanville/Zuma; Danny Feld/AP; Warner Bros./Everett; Daniel Mayer
- Name
- Brad Pitt
- Real Name
- William Bradley Pitt
- Birth Date
- 12/18/1963
- Birth Place
- Shawnee, Okla.
- Heart Monitor
-
Angelina Jolie, girlfriend (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)




