HOT GALLERY: Check Out Gossip Girl Stars Before They Ruled The Upper East Side

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Blake Lively, Eighth Grade Yearbook Photo, 2001, John Muir Middle School, Burbank, California

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Blake Lively as Serena van der Woodsen on Gossip Girl

Serena has it all: beauty, money, intellect, and handsome men. But personal, professional, and academic happiness has seemed to elude her through the years. Finally fed up with the way Gossip Girl ruins the lives of those she loves, she’s took a stand with her own blog. By the end of the series, after many a love interest, Serena finally figures out her true love and her career path.

chace crawford yearbok high school young 2003 photo

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Chace Crawford, Senior Year Yearbook Photo, 2003, Trinity Christian Academy, Addison, Texas

chace crawford yearbok high school young 2003 gossip girl tv photo

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Chace Crawford as Nate Archibald on Gossip Girl

As a member of the Vanderbilt family, Nate has weathered his share of success and scandals. Now at the helm of the Spectator, Nate makes the editorial choice to publish Dan's serialized articles which threaten the publication.

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Ed Westwick at 2006 CW Upfronts

ed westwick cw up front 2006 gossip girl tv 2011 photo

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Ed Westwick as Chuck Bass on Gossip Girl

This dapper Brit hides his accent well as the entitled and charismatic ladies’ man Chuck Bass. Although once a self-centered playboy, Chuck has grown up over the years, realizing there’s more to life than booze and beautiful women—there’s also Blair. He was willing to give up on their love so she could find happiness, but the pair never could stay away from one another.

leighton meester yearbook high school young 2002 photo

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Leighton Meester, Sophomore Year Yearbook Photo, 2002, Beverly Hills High School, Beverly Hills, California

leighton meester yearbook high school young 2002 gossip girl tv 2011 photo

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Leighton Meester as Blair Waldorf on Gossip Girl

For a time, Blair switched her signature headband for a royal tiara after she married Prince Louis of Monaco. After their divorce, other flings and struggling to begin her fashion design career, Blair made her way back to Chuck.

michelle trachtenberg yearbook high school young 2001 photo

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Michelle Trachtenberg, Sophomore Year Yearbook Photo, 2001, Notre Dame High School, Sherman Oaks, California

michelle trachtenberg yearbook high school young 2001 gossip girl tv 2011 photo

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Michelle Trachtenberg as Georgina Sparks on Gossip Girl

Georgina does not come into lives unnoticed, and she has a particular talent for upending the lives of Manhattan’s elite. Her previous schemes included telling Dan he fathered her child—and her teaming up with the rest of the gang to do their dirty work ended the series with a bang.

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Penn Badgley, Seventh Grade Yearbook Photo, 1999, Charles Wright Academy, Tacoma, Washington

penn badgley yearbook young 1999 gossip girl tv 2011 photo

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Penn Badgley as Dan Humphrey on Gossip Girl

“Lonely Boy” lost Serena, lost the son he thought was his, and lost the fleeting possibility of romance with Blair. He did find literary success with the publication of his first book but alienated friends and family when they discovered it was about them. If possible things got worse for Dan, but by the end of the series, he got everything he wanted.

taylor momsen yearbook high school young 2007 photo

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Taylor Momsen, Eighth Grade Yearbook Photo, 2007, Herbert Hoover Middle School, Rockville, Maryland

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Taylor Momsen as Jenny Humphrey on Gossip Girl

Jenny Humphrey morphed from daddy’s girl to Brooklyn baddie over the course of a few seasons. Jenny set her sights on toppling Blair and Serena but ended up taking herself down instead. Jenny may have been written out of the show, but her mean girl ways will not be forgotten as easily.