From PEOPLE Magazine Click to enlarge
For a man whose very first attempt at screenwriting won him an Oscar, Matt Damon can be astoundingly shortsighted. Just last year the star and coauthor of the award-winning Good Will Hunting was comparing himself—unfavorably—to Hollywood pal Matthew McConaughey. "I'm not as good-looking as him," he told Vanity Fair in December. "I'm certainly never going to be anyone's sex symbol."

Guess again, Matt. With Courage Under Fire, John Grisham's The Rainmaker and Hunting notched on his belt, the 27-year-old Harvard dropout with the adorable grin and tousled sandy hair is the big screen's new boy wonder. This summer alone, he's starring in Steven Spielberg's World War II adventure saga Saving Private Ryan and the gambling drama Rounders, and is set to shoot the Anthony (English Patient) Minghella murder thriller The Talented Mr. Ripley. "There's something so apple pie about him," Minghella told TIME in December. "You know he was the bestlooking kid in his school, won all the awards at track and field and dated the most popular girl."

Or girls. The 5'11" Boston native, whose parents (Nancy, a professor of early childhood education, and Kent, a stockbroker) divorced when he was 2, was a heartbreaker even in high school. "Matt always had girlfriends," says actor Casey Affleck, younger brother of Damon's Hunting coauthor and best-pal-from-childhood, Ben. Success hasn't changed that. After briefly dating Rainmaker costar Claire Danes and conducting a seven-month romance with Hunting's Minnie Driver, Damon is now linked with Winona Ryder. Those actresses' high style, though, hasn't rubbed off on Matt: Damon knocks around Hollywood in jeans and a T-shirt. "I don't think he's very appearance-conscious; he's more about comfort," says friend and School Ties costar Cole Hauser. "He is as regular a guy as there is."