Damon graduates from Cambridge Rindge & Latin High, where he was active in theatre and friends with Ben Affleck. The pair held "business lunches" in the cafeteria to plot their careers. Damon attends Harvard, majoring in English literature. Just 12 credits shy of getting his degree, he drops out to pursue acting. First gig: a one-liner in 1988's Mystic Pizza with Julia Roberts.
Damon moves to L.A., where he rooms with Affleck and Affleck's brother Casey, and auditions for films such as Primal Fear (the part went to Edward Norton) and To Die For (Joaquin Phoenix won out). When he wasn't auditioning, Damon "sat around, ate Cheerios, played video games and scribbled in his notebook," Casey later tells PEOPLE. The scribbling eventually becomes Good Will Hunting, which they sell in 1994 to Miramax for $600,000.
School Ties, a film about a '50s prep school for boys and anti-Semitism, stars a group of hot young actors, including Brendan Fraser, Chris O'Donnell, Affleck and Damon.
Courage Under Fire starring Meg Ryan and Denzel Washington is released and features Damon in his breakthrough performance as a Gulf War veteran addicted to heroin. Damon drops 40 pounds in 100 days, eating only chicken, egg whites, steamed broccoli and plain baked potatoes, then running 12 miles a day. "By the end of it, if I stood up, I didn't have any energy," he tells PEOPLE.
In his first starring role, Damon appears as a crusading lawyer in a film adaptation of John Grisham's The Rainmaker, directed by Francis Ford Coppola and also starring Claire Danes, Danny DeVito, Danny Glover and Virginia Madsen. Damon plays a lawyer, fighting for a cancer patient who falls victim to a crooked insurance company and is unable to afford medical treatment.
With Damon and Affleck in lead and supporting roles respectively, Good Will Hunting is released in time for awards season and grabs nine Oscar nominations, including two for Damon (Best Actor and Best Original Screenplay with Affleck). Damon is suddenly Hollywood's "it" boy, winning a Golden Globe for best screenplay with Affleck for Good Will Hunting.
Affleck's girlfriend Gwyneth Paltrow introduces Damon to Winona Ryder at a New Year's Eve party, and they date until April 2000. But girlfriend of seven months, Good Will Hunting costar Minnie Driver, claims to have found out of her breakup from Damon's January 12 appearance on The Oprah Winfrey Show, where he said, "I care about her a lot. We kind of decided it wasn't meant to be." Driver calls the breakup "fantastically inappropriate."
Damon loses to Jack Nicholson in the Best Actor category, but he and Affleck win the best screenplay Oscar. Instead of taking girlfriends Paltrow and Ryder, Affleck and Damon take their mothers. Two months later, he makes PEOPLE's Most Beautiful list, and receives honorable mention in the magazine's annual Sexiest Man Alive issue in 2002, 2004, 2005 and 2006.
Steven Spielberg's World War II adventure Saving Private Ryan is released with Damon in the title role. The film nabs five Academy Awards including Best Director, eventually earning more than $216 million. In 1999, Damon and Affleck, through their Pearl Street production company, executive-produce The Third Wheel, which stars Luke Wilson and Denise Richards. But the film is shelved and released straight to DVD.
The Talented Mr. Ripley opens with Damon starring opposite Paltrow and Jude Law, as Tom Ripley, a charming young American in Italy who falls in love with his friend, then decides to kill him in order to take his place. It's an eerie turn for Damon, and a hugely successful film.
BIOGRAPHY (top to bottom): Phil Penman/Splash News; PHOTOFEST; 20th Century FOX/Everett; Miramax/Everett; Anna Belle/Star Max; Jim Smeal/WireImage; Hal Garb/AFP/Getty; David James/Dreamworks; Phil Bray/Paramount/Miramax