Happening indeed. Last fall, Damon starred as a young Southern lawyer in John Grisham's The Rainmaker, directed by Francis Ford Coppola. Then came Hunting, a December release about an emotionally troubled mathematical genius. The film scored nine Oscar nominations, including two for Damon (Best Actor and original screenplay), and one for Williams as Best Supporting Actor. "I can't even comprehend this," Damon said after getting the news. In September, Damon finished filming Steven Spielberg's next film, the WWII drama Saving Private Ryan, with Tom Hanks.
Damon worked hard for his piece of the celluloid. After years playing small supporting roles, he won a part as a heroin addict in 1996's Courage Under Fire and was so desperate to make an impression that he lost 40 pounds. "I was looking for something to set me apart: 'Look at what I'll do, I'll kill myself!' " he told Vanity Fair. "Directors took note of it." As did his costars. "It was amazing to watch his discipline," says Lou Diamond Phillips. "He kept to a diet of steamed chicken breast and steamed vegetables, and that's it. Matt likes to eat, so this was a huge undertaking for him." His family was less impressed. "He was obsessive about it," says his brother Kyle, 30, an artist. "I'm genuinely worried about him. I know he will sacrifice himself for other people." In fact, when filming was over, Damon told PEOPLE in 1996, he had to take "medication to right my body."
Now that he has been anointed one of Hollywood's up-and-comers, such excesses are no longer necessary. And though he spent a week working at a Memphis bar to prep for Rain maker's bartending scenes, he is no longer an all-work-and-no-play kind of guy. During Rainmaker's filming in late 1996 and early '97, he briefly dated Claire Danes, 18, who played his love interest. And he recently ended a seven-month relationship with Minnie Driver, his Hunting costar (and Best Supporting Actress nominee). "I care about her a lot," he said on Jan. 12's Oprah Winfrey Show. "We kind of decided it wasn't meant to be." Since then, he has been dating actress Winona Ryder, to whom he was introduced by Affleck's girlfriend, Gwyneth Paltrow.
Sensitive guy or serial heartbreaker? Let's just say Damon knows how to turn on the charm. Rainmaker's assistant casting director Anne Marie Caskey thought he had a crush on her during filming. "But then I realized he was just trying to catch on to my Memphis accent." Still, says Pamela Chapman, who played money-hungry Vera Birdsong in Rainmaker, "I couldn't believe he was from the North because he had such extremely good manners." The Boston native learned them largely from his mother, Nancy Carlsson-Paige, a professor of childhood education at local Lesley College, who raised her two sons in a Cambridge, Mass., cooperative (the boys' father, Kent Damon, a stockbroker who is divorced from their mother, lived nearby). "We didn't rebel much," says Kyle. "We didn't do drugs, stay out late or bad-mouth our parents."
As a child, says Carlsson-Paige, Damon was a natural performer. "He wore a superhero towel around his neck day in and day out for a couple of years," she says. A natural athlete who occasionally break-danced for money in Harvard Square, Damon was extremely popular at the public high school Cambridge Rindge & Latin. "He was the guy who sat in the back of the bus always making out with his girlfriends," says actor Casey Affleck, the younger brother of Damon's childhood friend Ben Affleck. After graduating in 1988, Damon—whose first film role was a one-liner in that year's Mystic Pizza—headed to Harvard University as an English major but dropped out after three years to pursue acting. He moved to L.A., bunked with the Affleck brothers and began making the audition rounds. When not auditioning for roles in Primal Fear (the part went to Edward Norton) and To Die For (Joaquin Phoenix won out), "basically, Matt sat around, ate Cheerios, played video games and scribbled in his notebook," says Casey. The scribbling turned into Good Will Hunting, and when Damon won the Rainmaker role—beating out Norton this time—Miramax sat up and took a renewed interest in the project.
Damon seems unaffected by his turn of fortune. "He makes fun of it himself," says Williams. "He's going to do great." Damon remains close to family—he brought Mom to the New York premiere of Hunting—and friends. "Matt's the first guy I'd call," Ben Affleck told Winfrey, "if I woke up in a hotel room with a dead hooker." He's also companionable in less theatrical circumstances. "Whenever he comes through town, he just wants to watch a movie or play video games or go to a bar," says old pal Aaron Stockard. But in one respect, says Stockard, Damon has changed: "He picks up the bill more often."
ELIZABETH LEONARD and CHAMP CLARK in Los Angeles, JENNIFER LONGLEY and TOM DUFFY in Cambridge and JANE SANDERSON in Memphis