Damon rejoined his friend Affleck (fresh from the summer action blockbuster Armageddon) in Dogma (1999), a sharp, irreverent comedy written and directed by Kevin Smith and also featuring the comedian Chris Rock. Near the end of 1999, he took on his riskiest role to date—that of Tom Ripley, a working-class young man who tastes the good life and will do anything to make it his own, in Anthony Minghella’s lush adaptation of Patricia Highsmith’s dark novel, The Talented Mr. Ripley. Costarring Jude Law as Dickie Greenleaf, the golden object of Ripley’s affection, and Gwyneth Paltrow as Greenleaf’s equally golden girlfriend, The Talented Mr. Ripley earned somewhat mixed reviews, but critics singled out both Damon’s and Law’s performances for praise. (Law received an Oscar nomination for Best Supporting Actor.)

In 2000, Damon lent his voice to the animated space epic Titan A.E., which met with a mediocre reception among critics and audiences. Later that year, he headlined an adaptation of Cormac McCarthy’s novel All the Pretty Horses (2000), as well as the golf comedy-drama The Legend of Bagger Vance (2000), directed by Robert Redford and costarring Will Smith.

Damon has been romantically linked in the past to costars Claire Danes and Minnie Driver. A two-year romance with the actress Winona Ryder ended in the spring of 2000.

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