Ryan Phillippe
From the daytime soap to teen idol, Ryan Phillippe was the smirking heartthrob who could play both the innocent and the seducer. I Know What You Did Last Summer introduced him; Cruel Intentions cemented him as the defining rich, dangerous charmer of his moment. He married Reese Witherspoon in 1999 and became one of the era's most visible celebrity couples before their 2006 separation.
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.
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Cruel Intentions
A sharp, seductive update of Laclos' 1782 novel Les Liaisons dangereuses transplanted to Manhattan's prep-school elite, starring Sarah Michelle Gellar and Ryan Phillippe. Written and directed by Roger Kumble, it became a defining late-90s teen drama with genuine cultural impact.
Antitrust
A tech-industry thriller starring Ryan Phillippe as a young programmer recruited by a charming but sinister software CEO (Tim Robbins) who steals code and eliminates threats. Released with Microsoft's real antitrust battle still in the headlines, it became a cult artifact of the dot-com era despite critical and commercial failure.
Reese Witherspoon
The teenager with a critic's favorite first kiss who grew into the 2000s' defining star. Southern charm and comic precision built through the '90s—Fear, Freeway, Election—but then Legally Blonde detonated, and she owned the decade. Walk the Line proved she could do Oscar-worthy dramatic work. Married and divorced Ryan Phillippe in a trajectory as public as her career was inescapable.
Jessica Biel
The church-family daughter from 7th Heaven who shed her wholesome image and fought her way into 2000s movie stardom. Cast at fourteen as Mary Camden, she became one of The WB's defining faces—and by her early twenties she was headlining studio films like The Texas Chainsaw Massacre and Blade: Trinity.