Ryan Phillippe

Born in New Castle, Delaware, Phillippe began his career on daytime television, playing Billy Douglas on ABC's One Life to Live (1992–93)—a role that made history as the first gay teenager on a daytime soap opera. His film breakout came with I Know What You Did Last Summer (1997), where he played Barry, establishing him as a rising talent in teen-oriented thrillers.

The late 1990s and early 2000s were his era. In 54 (1998), he played the bartender Shane O'Shea in a period dive into New York's nightlife. Then came the role that defined him: Sebastian Valmont in Cruel Intentions (1999), opposite Reese Witherspoon. With his smirk and his aristocratic scheming, he became the era's definitive rich, dangerous charmer—the seducer with a heart just wounded enough to be compelling. Witherspoon and Phillippe had met at her 21st birthday party in March 1997; they married on June 5, 1999, at the height of their mutual visibility, becoming one of Hollywood's signature couples. His roles in Antitrust (2001)—where he played Hollywood's go-to young programmer—and the ensemble turn in Gosford Park (2001) kept him at the center of the moment.

The couple separated in 2006, with the divorce finalized in 2007, marking the end of one of the era's most public partnerships. Though Phillippe appeared in Crash, the Best Picture Oscar winner released in 2005, that success came as his peak-era reign was fading. The 1990s and early 2000s had belonged to him; everything that followed was a recalibration.