Word: actorly
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Dates: during 1990-1999
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...them acquire a 25% stake in then troubled Disney, pocketing a reported $50 million for himself in the process. His work with Disney helped him befriend Hollywood heavyweights like Michael Eisner and Michael Ovitz, and in 1994 he joined the Beverly Hills crowd by buying the old estate of actor Sidney Poitier. In 1989 he helped finance a $3.65 billion leveraged buyout of Minnesota-based Northwest Airlines, investing about $12 million of his own money. Today much of his fortune is based on the 11.4 million shares he holds in the company...
...they saw in Damon the same thing Hollywood does--an all-American beer-drinking dude, with an appealing self-assurance. The 27-year-old actor's gambling strategy was to raise, raise, raise--an approach that suited a wealthy young man whose annual salary just went north of $1 million, but whose cards weren't what you'd call a sure thing. Long after lower-paid mortals folded, Damon continued to bet like a winner; he'd arrived at the table with $200 and left only $20 poorer, which of course did nothing to deter the amiable grin that rarely...
...reminiscent of De Niro's weight gain for Raging Bull, Damon dropped 40 lbs. for a two-day scene opposite Denzel Washington. It created an anorexia-like medical condition (from which he only recently recovered), but the intensity of his performance convinced the industry that Damon was a serious actor...
...that time Damon had taken steps to ensure that Hollywood would take notice of more than his acting. With Stallone-like hubris, he and best friend Ben Affleck--another hot actor, who starred in Chasing Amy and grew up two blocks away from Damon--wrote the screenplay for Good Will Hunting, based on a play Damon had started writing as a Harvard student. (He still has two semesters to go for his degree.) Damon and Affleck attached themselves to the project as stars. The script--about the struggles of a young working-class math genius in South Boston--sold...
...making his lofty ambitions clear as early as 1993, when, after small but memorable performances in the 1992 film School Ties and 1993's Geronimo: An American Legend, he was offered a part in the Sharon Stone movie The Quick and the Dead--a highly coveted job for an actor still sleeping on a friend's couch. But Damon didn't like the script and wanted to pass. "You know what I did last night? I watched Bullitt," he remembers telling his agents. "Robert Duvall drives a cab in that movie, and he has, like, four lines...