With Damon in the lead, and Affleck, Minnie Driver, and Robin Williams in crucial supporting roles, Good Will Hunting became a sleeper hit in 1997, scoring nine Oscar nominations, including nods for Best Actor (Damon), Best Supporting Actor (Williams), Best Supporting Actress (Driver), Best Director (Gus Van Sant), and Best Picture. While Damon lost out to Jack Nicholson in the acting category, he and Affleck took home the award for Best Original Screenplay, an achievement that kicked both their careers into high gear.

In 1998, Damon played the title role in Steven Spielberg’s World War II epic Saving Private Ryan, one of the most acclaimed films of the year. As the stubborn young Ryan, Damon held his own opposite the movie’s star, Tom Hanks, who played the leader of a small group of men sent to find Ryan and send him home for the sake of his mother after all four of his brothers are killed. That same year, he starred as an earnest law student and reformed poker player in Rounders, also featuring Edward Norton and John Malkovich.

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.