Ryan Phillippe

Phillippe got his first break on the ABC soap opera One Life to Live, on which he portrayed daytime's first gay teenager, Billy Douglas. The role, which he played from 1992 to 1993, won him both favorable notices and increasing recognition. After quitting the show to focus on his screen career, Phillippe got a small part in 1995 submarine action thriller Crimson Tide. More work -- and more boat-oriented action -- followed in 1996 with Ridley Scott's White Squall, in which Phillippe was given a prominent role alongside two other up-and-coming actors, Ethan Embry and Scott Wolf. After this mainstream, big-budget venture, Phillippe took a walk down the yellow brick road of independent filmmaking, first with his starring role as an abused trailer-park teen in Little Boy Blue (1997), and then in Gregg Araki's Nowhere (1997), as the latest of Araki's trademark ultra-horny boys.

Phillippe's major screen break came with his role in the formulaic 1997 slasher pic I Know What You Did Last Summer, in which he starred alongside fellow Next-Big-Things Jennifer Love Hewitt, Freddie Prinze Jr., and Sarah Michelle Gellar. The film's success, coupled with Phillippe's exposure from previous films, was enough to propel him into two leading roles in 1998, first as a blue-haired club baby in Playing by Heart, and then as a starry-eyed bartender in the critically disembowelled 54, a film which showcased Phillippe's abs over his acting.

Following 54, Phillippe opted to play a naïve dope farmer in the obscure Homegrown (1998), in which he co-starred with Billy Bob Thornton and Hank Azaria. This preceded his next big break as the petulantly seductive trust-fund brat Sebastian Valmont in 1999's Cruel Intentions, a film that was essentially a present-day, all-teen adaptation of Choderlos de Laclos' Les Liaisons Dangereuses. Co-starring Sarah Michelle Gellar as his scheming stepsister and Phillippe's real-life wife-to-be Reese Witherspoon, the film proved to be one of the year's most guilty pleasures, winning Phillippe further acclaim in the hearts and minds of lust-struck women and men alike.

Subsequently teetering on the brink of all-out superstardom, Phillippe faltered a bit with the late summer 2000 action thriller The Way of the Gun, co-starring Benicio Del Toro. Though some saw the film as a smartly penned meditation on violence, others brushed it aside as just another post-Tarantino study in excess, and the film faded quickly from the box-office radar -- with the following year's AntiTrust dissipating almost immediately following its January 2001 release. But the tables turned for Phillippe in the years to come, with involvement in films that consistently found dual favor with critics and audiences -- and thus helped the young actor transition from a widespread reputation as a heartthrob to a reputation as an immensely gifted dramatist graced with a succession of plum roles (and suggested a keen instinct for script selection). This turnaround began with the actor's participation in director Robert Altman's critically worshipped mystery comedy Gosford Park. Phillippe (as Henry Denton) was not among the top-billed members of the ensemble cast, but his work shone brightly alongside such luminaries as Maggie Smith, Michael Gambon, Helen Mirren, and Kristin Scott Thomas -- no small feat for a relative newcomer.

The following year, Phillippe drew raves for his work in Burr Steers's sleeper hit Igby Goes Down (2002) -- a commercial and critical indie darling -- as the spoiled, conceited older brother of the title character. Thereafter, Phillippe's screen activity declined just a bit (perhaps because of his off decision to father and raise additional children with wife Witherspoon), but he also became increasingly selective. His star rose higher with 2005's Best Picture winner Crash, directed by Paul Haggis. A Gaghan-esque muckracking drama with a massive ensemble cast that included the gifted Don Cheadle, Matt Dillion, and Brendan Fraser, the picture meditated on modern-day racism through multiple interlocking stories that unfold throughout the City of Angels.

2006 marked a fortuitous year for Phillippe. He secured a leading role in director Clint Eastwood's Flags of Our Fathers, the American half of the director's two-part dramatization of the Battle of Iwo Jima (as Bradley, a man who learns of his father's heroism in that conflict decades later). In that same year's Lionsgate release Five Fingers, helmed by neophyte Laurence Malkin, Phillippe plays the difficult role of a brilliant Dutch pianist abducted by terrorists and threatened with having his fingers lopped off one by one. At about the same time, Phillippe signed on (alongside Chris Cooper and Laura Linney) to play Eric O'Neill in director Billy Ray's Breach, which the studio slated for a 2007 release. The picture -- a docudrama -- concerns real-life FBI turncoat Robert Hanssen (Cooper). Phillippe plays the "mole" assigned to catch Hanssen in the act.

Also in the fall of 2006, the busy Phillippe had to contend with drama in his personal life in the form of a highly public divorce from Witherspoon, announced that October. ~ Rebecca Flint Marx, All Movie Guide