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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).In the former's first installment, Steven Soderbergh's 2001 ensemble film Ocean's Eleven, which is a remake of the Rat Pack's Ocean's 11 (1960), he co-starred as thief Linus Caldwell.
Variety said of his work in All the Pretty Horses: "[Damon] just doesn't quite seem like a young man who's spent his life amidst the dust and dung of a Texas cattle ranch.
Damon, alongside Affleck and others, produced the documentary series Project Greenlight, aired on HBO and later Bravo, which helps newcomers develop their first film.
The series was nominated for the Primetime Emmy Award for Outstanding Reality Program in 2002, 20.
Damon is also known for his starring roles as Jason Bourne in the Bourne franchise (2002–2016) and as a con man in the Ocean's trilogy (2001–2007).
For his supporting role as the rugby player Francois Pienaar in Invictus (2009) and his leading role as an astronaut stranded on Mars in The Martian (2015), Damon received Academy Award nominations for Best Supporting Actor and Best Actor, respectively.