1999-2001

Penn Badgley

Soapy Roots

After performing in the Seattle Children's Theater, Badgley lands on an episode of Will & Grace. But it's his stint in Genoa City on The Young and the Restless as Phillip Chancellor IV that earns him a Young Artist Award nomination for Best Performance in a Daytime Series.

2002

Penn Badgley

September 19

The WB Rounds

In the WB's Do Over, a 15-year-old Badgley (pictured with costar Natasha Melnick) plays Joel, a 34-year-old reliving his life from the age of 14. Although the series fails, the network is good to Badgley. The teen actor appears in other short-lived series, including the 2004 family drama The Mountain and the 2006 sex-ed show The Bedford Diaries with Milo Ventimiglia. "It definitely felt like, 'What can we put Penn in this year because we want to keep him working for us?'" Badgley tells the New York Post in 2007. "There was a time when I felt a little cheesy, doing WB show after WB show – like it was repetitive."

2006

Penn Badgley

July 28

The Other Tucker

At 19, Badgley lands on the big screen in John Tucker Must Die, where he plays Scott, John Tucker's (played by Jesse Metcalfe) younger brother, who has a crush on Kate (played by Brittany Snow). The New York Times, which calls Badgley "wildly charismatic," says "The entire picture could hang on his cheekbones alone."

2007

Penn Badgley

September 19

XOXO, Gossip Girl

Surrounded by rich Manhattanites, Badgley plays Brooklyn outcast Dan Humphrey in the CW's Gossip Girl. "He casts himself out because he doesn't agree with the privileged kids' lifestyle," Badgley tells CosmoGIRL!, "but he's conflicted because he's in love with the girl who embodies all of that." The breakout hit costars Blake Lively, Leighton Meester, Chace Crawford, Ed Westwick and Taylor Momsen.

2008

Penn Badgley

March

The Boys Are Out

With Gossip Girl costars Crawford and Westwick, Badgley appears on Out. The gay and lesbian 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." Badgley says, "I?m kind of stunned by how seriously people in the media are taking our high-camp TV show."

Penn Badgley

April 28

GG Conquers New York

The cast of Gossip Girl, including newcomer Jessica Szohr, strips down for a tantalizing cover of New York magazine, which calls the teen soap, "the most awesomely awesome show ever." That week, the entire cast also lands on PEOPLE's Most Beautiful List. Tooting his castmates' horn, Badgley tells PEOPLE, "I assure you, we are all fun and charming as hell."

Penn Badgley

May

Blake & Penn Go Public

After months of swearing there's no romance with his Gossip Girl castmate Blake Lively, Badgley hits an afterparty following the Met's Costume Institute Gala with Lively on his arm. "I think she's incredible," he tells PEOPLE. "She's an amazing person and she's beautiful – so there's not a lot to dislike." But the real confirmation comes the following week when the pair is photographed canoodling in Cancun.

Penn Badgley

November

Badgley Spills the Details

The boys of Gossip Girl put their smoldering good looks to use on the November cover of Details. Badgley and costars Crawford and Westwick share their outrageous fan experiences, which seem destined to intensify as the second season nabs its highest ratings yet with 3.7 million viewers. "I get a lot of guys coming up to me who are like, 'Oh man, my wife loves the show,'" says Badgley. "Couple of drinks later they come up and they're like, 'You know what, I love Dan.' And they probably watch the show more than their wives."

2009

Penn Badgley

October 16

The Stepfather

Badgley stars as a reformed delinquent teen suspicious of his mom's fiancé in The Stepfather, a remake of the 1987 film. "It's a slower, simpler movie that draws you in and I think really terrifies you once you're in there," he tells MTV of the film which makes $11.5 million during its opening weekend. In 2010, he nabs another box office hit with the teen comedy Easy A.

2010

Penn Badgley

October

Penn & Blake's Split Decision

After dating for more than two years, Badgley and Lively call it quits, reps for both stars confirm to PEOPLE. The private actor once told Details magazine that mixing work and romance with his Gossip Girl costar was "wonderful and also something to grapple with."

Photo Credits

BIOGRAPHY (top to bottom): Everett Collection; Everett Collection; CBS; courtesy New York Magazine; NPG; Chuck Zlotnick/Columbia; INF

Edited by Julia Wang

Penn Badgley

Celebrity Central / Top 25 Celebs

 

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