- 2002


Critical Darling
Witherspoon is quickly becoming an A-list celebrity with the runaway successes of Legally Blonde and Sweet Home Alabama. Meanwhile, Phillippe quietly takes roles in the critically acclaimed films Igby Goes Down and Robert Altman's Oscar-winning ensemble drama Gosford Park. The New York Times lauds Phillippe's performance in Igby, recognizing how Phillippe, as the older brother Oliver, "finds a hint of vulnerability in this cold, condescending smoothie."


She's the Boss
While jointly presenting the award for Best Makeup at the 2001 Academy Awards with Witherspoon, Phillippe makes a joke about his wife's earning power. "Let me read it?" she asks him. "You make more than I do," he quips, pointing at the envelope. "Go ahead."
- 2003


Growing Pains?
Phillippe and Witherspoon add a son, Deacon, to the family. They take turns filming so one parent is always at home with the children. Both acknowledge the difficulties in being a young star couple. They talk openly about being in couples therapy and constantly working on their relationship. "We're normal people with normal problems," Witherspoon says to PEOPLE. Phillippe concurs, telling New York Daily News, "The biggest mistake is...having the marriage fall apart because of laziness."
- 2006


Celebrate Gold Times
When Witherspoon wins a Golden Globe for her portrayal of June Carter in Walk the Line, Phillippe celebrates, waving his arms in the air, screaming and jumping. In October, he explains his behavior to Rolling Stone, "I was plastered [at the Golden Globes]! Shirley MacLaine and I drank like crazy, just putting away bottles of wine and making fun of everyone." In the same interview, he also describes his desire to live in the Caribbean, "probably smoking herb."


More Than a Pretty Face
The actor plays an impressionable rookie, opposite Matt Dillon's racist cop, in Crash. The movie wins Best Picture the night Witherspoon takes home the Oscar for Best Actress. Phillippe tells the Los Angeles Times, "She's great at what she does. I am proud of her."


Soldier On
Phillippe turns in another critically acclaimed performance, this time as a leading man, in Clint Eastwood's war drama, Flags of Our Fathers. He plays one of the flag-raising heroes featured in the historic Iwo Jima photograph. Rolling Stone applauds his portrayal of John "Doc" Bradley, the film's "emotional center," as a "hauntingly implosive performance." Phillippe tells the Chicago Sun-Times, "This is the first film where I had this immediate feeling that my children will be proud of their father."


The Golden Couple Splits
After seven years of marriage, Phillippe and Witherspoon announce their separation, and Witherspoon later files for divorce. Phillippe, who is rumored to be involved with Australian costar Abbie Cornish, 24, issues an exclusive statement to PEOPLE: "I'm not a perfect person, but I'm not guilty of a lot of the things I have been accused of." In 2008, they finalize their divorce.
- 2008


Phillippe in Stop-Loss
Phillippe stars in Stop-Loss, with Cornish and Channing Tatum. In the film, which is written and directed by Kimberly Peirce (Boys Don't Cry), Phillippe plays a soldier who returns home and refuses to go straight back to Iraq.


Ryan Steps Out With Abbie
With ex-wife Witherspoon with Jake Gyllenhaal, Phillippe moves on with his love life as well, stepping out with Cornish at the 2008 Australian in Film Breakthrough Awards. "They were adorable," says a guest of the couple, who have been under the watchful eye of the media for months. "He had his arm around her and they were cozy and comfortable."
Photo Credits
BIOGRAPHY (top to bottom): Everett; John McCoy/LADN/WireImage; MWD/X 17; Kevin Mazur/WireImage; Mambo/ZUMA; Merie W. Wallace/Paramount; Everett Collection; Kevin Winter/Getty
- Name
- Ryan Phillippe
- Real Name
- Matthew Ryan Phillippe
- Birth Date
- September 10, 1974
- Birth Place
- New Castle, Del.
- Heart Monitor
-
Abbie Cornish, girlfriend (2007 to present)
Reese Witherspoon, ex-wife (1997 to 2006; divorced finalized in 2008)




