Becoming ... Brad Pitt

01 of 11

HIGH SCHOOL STAR

Even with those wings, as a senior at Springfield, Mo.'s Kickapoo High School, Pitt (in 1982) "always had a lot of dates" and was named best dressed, said classmate Mark Swadley.

02 of 11

SO SEXY

Pitt was named PEOPLE's Sexiest Man Alive in 1995, then again five years later. But it's not just because he's hot: "I know it sounds cliché," said Fight Club costar Helena Bonham Carter, "but what makes him really attractive is internal – his humor and caring and curiosity."

03 of 11

EYE CANDY

With a new girlfriend (Kalifornia costar Juliette Lewis) on his arm and a different look, Pitt exhibited the makings of a megastar leading man in 1991. "He's like a painting," Lewis said at the time. "I'd like nothing better than for him to become the next Robert Redford."

04 of 11

ON HIS WAY

A year after dropping out of the University of Missouri, Columbia, and heading to Hollywood, Pitt in 1987 gained roles on TV shows such as Dallas and Growing Pains. "I saw his picture in the casting office and I said, 'You have to hire him,'" recalls Pains star Tracey Gold. "It was just like, Hell-o, hell-o, my God!"

05 of 11

DISH-EVELED

For his roles in 1994's Legends of the Fall and Interview with the Vampire, Pitt grew his hair long – and kept it that way – proving he's got more than cookie-cutter leading-man looks. "He likes to appear a little sloppy and unshaven," said writer Karen Hardy-Bystedt, who interviewed Pitt for a book titled Before They Were Famous.

06 of 11

IT COUPLE

Pitt met Gwyneth Paltrow on the set of the 1995 thriller Seven and called her his "angel, the love of my life" at the 1996 Golden Globes. That December, Pitt proposed with a ring of his own design, but the pair (in 1997) split six months later.

07 of 11

BAD HAIR DAY?

Although he's one of Hollywood' most bankable stars, not all of Pitt's projects are sure things. For his role in the sci-fi film The Fountain, Pitt (in 2002) let his beard grow ... and grow, and grow, only to shave it off after dropping out of the film over a rumored disagreement with scriptwriter Darren Aronofsky.

08 of 11

ABS-OLUTELY FABULOUS

In his breakout role in 1991's Thelma amp Louise, Pitt displayed more than just his acting chops – his devilish grin and six-pack abs were impossible to miss. "Even though he's obviously a great-looking guy ... he's got great looks with a soul," said the film's casting director, Louis DiGiaimo. "And that's what I think comes across."

09 of 11

THAT'S AMORE

Ah, love! It certainly looks good on Pitt and Jennifer Aniston (in 2003), who, after being set up by their agents in 1998, married two years later.

10 of 11

BOLD MOVE

Pitt's role in the violent 1999 thriller Fight Club was a risky one. The film was released just five months after the Columbine shootings and amid Congressional calls for laws regulating violence in entertainment. Indeed, the public did not have the stomach for the film's gory fight scenes: It had a $63 million budget and grossed only $37 million.

11 of 11

WARRIOR GOD

Pitt worked out six days a week for eight months to achieve the body of Achilles (left), his character in the $200 million epic Troy. This month, Aniston joined him at the movie's New York premiere, amid rumors their marriage was in trouble, following photos of her kissing Friends co-star Matt LeBlanc and Pitt with Mr. amp Mrs. Smith co-star Angelina Jolie.