Why Sebastian Valmont From Cruel Intentions Looks So Familiar

"Cruel Intentions" became a sleeper hit with audiences when released in 1999, the $10.5 million-budgeted film pulling in more than $70 million worldwide (via Box Office Mojo). The movie, written and directed by Roger Kumble, is an updated retelling of the 1782 novel "Les Liaisons dangereuses" by Pierre Choderlos de Laclos and the 1988 English adaptation "Dangerous Liaisons" (via Telegraph). 

The lasting impact of the New York City-set tale of love and manipulation is evidenced by the fact that it has spawned an entire franchise: Following the 1999 cult film, there was a straight-to-video (blast from the past!) prequel and sequel, the prequel written and directed by Kumle again, with the sequel actually coming courtesy of a script from "Deadpool" co-writer Rhett Reese. A pilot for a sequel series was also produced, but unfortunately did not move forward in 2016 (per Deadline).

More evidence of the movie's lasting success is the breakout stardom of its young cast. Sarah Michelle Gellar, Selma Blair, Reese Witherspoon, and others all went on to major roles in future projects. It's likely they are all familiar in one way or another to most viewers, and that also goes for the film's leading man, Ryan Phillippe, who you certainly recognize from other projects.

Like so many actors, Ryan Phillippe began his acting journey in the world of soaps. He appeared on 13 episodes of the long-running "One Life to Live" as the character Billy Douglas from 1992 to 1993.

The role was significant for the series as it was the show's first openly gay character, and Phillippe has revealed since that taking on the role caused friction with his parents. "I was shunned at that point ... I mean, this was 1992 and I was playing a gay teenager and I was in a Christian school. They weren't happy about it," he told KFC Radio (via Soap Central).

Despite being told it was a "risky" role at the time, Phillippe made a splash with the character and managed to stand out in constant melodrama of soaps enough for him to make his way to the big screen.

After a few years of small roles in some major releases, including Ridley Scott's "White Squall" and Tony Scott's "Crimson Tide," Phillippe got a chance to be one of the leads in a movie that would go on to become a massive box office success and bring back the slasher genre in a major way.

In 1997, Phillippe starred in "I Know What You Did Last Summer," a movie that would earn over $120 million worldwide (via Box Office Mojo). The film injected new life into the horror genre, inspiring countless ripoffs, two straight-to-video sequels, and even a recent Amazon TV series. The cast of the Kevin Williamson-penned movie was full of future stars, including Sarah Michelle Gellar, and Jennifer Love Hewitt. As for Phillippe, he starred as Barry Cox, a bratty rich kid and one of a group responsible for a man's death ... and later hunted for burying the incident. Phillippe would, of course, go on to reteam with Gellar, his one-time wife, on "Cruel Intentions," a very different take on the "bratty rich kid" persona Phillippe introduced here.

Following years of experimenting on various projects and with his image in various projects like 2001's "Gosford Park," Ryan Phillippe managed to shed his slasher and melodramatic past in the eyes of critics by joining the ensemble cast of 2004's "Crash."

Phillippe starred as Tom Hansen, a Los Angeles cop who finds his moral line and subconscious prejudices tested in just one of many stories that make up the film. The movie has its detractors, but it made a splash when it debuted at the Cannes Film Festival and would go on to win the Academy Award for Best Picture (per Variety). While Phillippe wasn't singled out by the Oscars, he and the film's other performers, including Brendan Fraser and Sandra Bullock, won Outstanding Performance by a Cast from the Screen Actors Guild Awards. Phillippe would continue showing off his dramatic chops around this time in films like 2006's "Flags of Our Fathers," directed by Clint Eastwood.

Ryan Phillippe would once again reinvent himself in 2010 by dabbling in a new genre with "MacGruber," one of a handful of film adaptations of "Saturday Night Live" running sketches. In the comedy film, Phillippe starred as Dixon Piper, a straight man of sorts to Will Forte's MacGruber, a parody of the MacGyver persona. "MacGruber" did not exactly light the world on fire when it was released in 2010, not even earning back its $10 million budget in theaters (via Box Office Mojo).

"MacGruber" has stood the test of time, though, and went on to earn a pretty big cult following, with the cast — also featuring Kristen Wiig and Val Kilmer — especially getting praise from fans. Demand for a follow-up reached such a fever pitch that "MacGruber" was brought back last year for a TV series with the Peacock streaming service, with Phillippe getting back in on the laughs.

Ryan Phillippe began his career in soaps, broke out with a slasher flick, jumped in and out of highly-praised comedies and dramas. So, what is left for the filmmaker to do? Action, of course.

Phillippe had dabbled in the action genre in the past with cult films like director Christopher McQuarrie's "The Way of the Gun," but his first big hit in the genre was as former Marine sniper Bob Lee Swagger in "Shooter," a series that ran for three seasons on USA Network. Produced by Mark Wahlberg, the show serves as a reboot of the 2007 film by the same name, moving on from the movie and adapting further books in the "Swagger" series by Stephen Hunter.

"Shooter" had a strong debut for its network in 2016, bringing in 1.4 million viewers (per Deadline). What was shocking about the series was how action-heavy it became and how much Phillippe was called on to do. He proved himself up to the task, but the show was unfortunately canceled after a leg injury cut Season 2 short and kept viewers waiting on Season 3 (via Deadline).

Since starring on and producing the show, Phillippe has continued dabbling in action movies, starring opposite Casper Van Dien in 2020's "The 2nd," also produced by Phillippe, and Scott Adkins in 2021's "One Shot."