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The Washington Post concluded, "Damon, constantly flashing his newscaster's teeth and flaunting a fake, 'Masterpiece Theatre' dialect, comes across like someone who got lost on the way to an audition for a high school production of The Pirates of Penzance." The film focuses on petroleum politics and the global influence of the oil industry.
Damon says starring in the film broadened his understanding of the oil industry and that he hoped the people would talk about the film afterward.
He co-starred with Edward Norton in the 1998 poker film Rounders, where he plays a reformed gambler in law school who must return to playing big stakes poker to help a friend pay off loan sharks.
Despite meager earnings at the box-office, the film has developed a cult status over the years.
He continued to garner praise from critics for his roles as the eponymous character in Saving Private Ryan (1998), the antihero in The Talented Mr.
Ripley (1999), a fallen angel in Dogma (1999), an energy analyst in Syriana (2005), and a corrupt Irish-American police officer in The Departed (2006).
The latter also won him a Golden Globe Award for Best Actor.
Damon said that before The Bourne Identity he was jobless for six months, and many of his films during that period under-performed at the box-office.
He has been involved in charitable work, including the ONE Campaign, H2O Africa Foundation, Feeding America, and
Damon is married to Luciana Bozán Barroso, and they have three daughters together.
Damon then portrayed antihero Tom Ripley in The Talented Mr.
Ripley (1999), a role for which he lost 25 pounds (11 kg).Nor does he strike any sparks with [Penelope] Cruz." During this period, Damon joined two lucrative film series—Ocean's Trilogy (2001–2007) and Bourne (2002–2016)—and produced the television series Project Greenlight (2001–2005, 2015).