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After Ripley, for which he lost 25 lbs. in order to appear pale and skinny, Damon spent a month learning to ride and bulking up for his portrayal of an 18-year-old cowboy in All the Pretty Horses, which will be released in late 2000. When Ripley director Anthony Minghella visited Damon on that set, he barely recognized him. "He was like the more successful, more centered, more handsome, just generally more masculine and surefooted cousin of Ripley," he says. And as Damon conducted a barrage of press interviews for Ripley, he was squirming under a brace because he had separated a rib while swinging a golf club for yet another role, as a World War I veteran who finds enlightenment through his caddy in The Legend of Bagger Vance, which is being directed by Robert Redford. "Matt seems to work on a process of 'If it doesn't hurt, it can't be right,'" says Minghella. Damon shrugs off the compliment. "I just don't think there's an excuse for not working as hard as you can," he says.
Ironically, the star and the guilt-ridden murderer have something else in common. Both Ripley and Damon work their way through conversations like poachers in Yellowstone. They sense they're being watched, so they constantly observe themselves. Halfway through talking about the responsibilities of fame and how it should be used for good, Damon breaks off. "Oh God," he says. "I sound like Miss America." He seems to have an acute sense of what others, particularly reporters, want to hear. He talks sports with the guys. He does classic movie routines with the show-biz old-timers. To a thirtysomething female, he talks mostly about his mother.
The glaring difference between Ripley and Damon is that Damon has managed to pull off what Ripley doesn't: he has achieved the trappings of privilege and success, but not, it seems, at the expense of his soul. Partly this is thanks to the support of his friends, most famously his childhood buddy Affleck, with whom he has been so closely entwined in the public eye that they now try to avoid speaking about each other to the press. ("It's not like we're bitching ex-husbands, or anything," Damon says.) More important, it's thanks to his family. They're quite a clan: liberal, intellectual, active in social causes, politically sophisticated. "They're the most fun, most interesting people," says Skylar Ulrich, the former girlfriend who was the model for the role Minnie Driver played in Good Will Hunting, and who's now a doctor, married to Metallica drummer Lars Ulrich. "They're really tight knit, and yet they're very individual."