2000s

Chace Crawford

Chace's University Days

Crawford, the son of a dermatologist, works as a model while attending Trinity Christian Academy. After graduation in 2003, he heads west to Malibu's Pepperdine University. "Everyone else knew what they wanted to do," Crawford tells Teen Vogue in 2007. "But not me – I was the lone wolf." He eventually tries his hand at auditioning for commercials.

2006

Chace Crawford

September 04

The Covenant

Crawford lands his first major role in the supernatural thriller, The Covenant (right). He plays one of the four males leads, which includes the equally gorgeous Taylor Kitsch of NBC's Friday Night Lights. The film opens at No. 1, grossing more than $23 million.

2007

Chace Crawford

September 19

Gossip Girl: Being Nate Archibald

Crawford dons prep school blazers and khakis to play conflicted hunk Nate Archibald in Gossip Girl, The CW's adaptation of the juicy novels by Cecily von Ziegesar. The teen drama follows a group of rich New York City Upper East Siders. "I'm proud to be part of a show that's kind of redefining what it means to be a hit show with today's younger generation that is very media-savvy," Crawford (pictured with onscreen girlfriend Leighton Meester) tells the Los Angeles Times. The series costars Blake Lively (Serena), Penn Badgley (Dan), Ed Westwick (Chuck) and Taylor Momsen (Jenny).

Chace Crawford

October

A Coy Connection: Chace & Carrie

Crawford, 22, is spotted out on the town in New York City with country music sensation and American Idol winner Carrie Underwood (right), 24, but the singer downplays the relationship. In April 2008, Underwood confirms a split: "We've parted ways. I actually haven't spoken to him in over a month." PEOPLE reports that sources say Underwood broke Crawford's heart, but he was the one who decided it wasn't meant to be.

2008

Chace Crawford

March

Gossip Boys Cover Out!

With Gossip Girl costars Ed Westwick (left) and Penn Badgley (right), Crawford appears on gay and lesbian lifestyle magazine Out. The magazine calls the show a "cultural phenomenon whose early adopters weren't actually teenage girls but rather gay men trapped in arrested development or seeking to vicariously prolong their youth." Later that month, former 'N Sync star JC Chasez dismisses online speculation that he and Crawford are more than friends as a lie and "outright stupid."

Chace Crawford

April 28

Gossip Girl Cast Covers New York!

The cast of Gossip Girl strips down for a tantalizing cover of New York magazine, which calls the teen soap, "the most awesomely awesome show ever." Of the coverage about his relationship with Underwood, Crawford tells the magazine, "I wasn’t ready for all that craziness. I didn’t realize what that was going to entail." That week, the entire cast also lands on PEOPLE's Most Beautiful List.

Photo Credits

BIOGRAPHY (top to bottom): Splash News Online; Everett Collection; CW; INF; courtesy New York Magazine

Edited by Mai Dinh, Janet Murphy