15 Years Later: Looking Back on Vanity Fair‘s Young Hollywood

In Hollywood, there’s always a battle for attention. The legends and icons are forced to fend off the pretty young things that pop up every year. But sometimes, a generation of starlets and studs are more than just pretty faces — they are the new Hollywood. They transform into talented, award-winning actors who take over both the big and small screen. They include the likes of Jonah Hill, Carey Mulligan, Emma Watson and Shailene Woodley, all of who have been featured in Vanity Fair’s Young Hollywood series.

While there have been a number of hits featured in the magazine of the years, there have also been a number of misses — Vinessa Shaw and Sarah Wynter anyone? Like them, we want to know where they are all now.

Starting with 1999 — the unofficial “Young Hollywood” issue — we look back on the hottest, youngest, brightest, freshest faces of the past 15 years.

The Class of 1999

  • [Photo Credit: Vanity Fair]

  • [Photo Credit: Getty Images]

  • [Photo Credit: Getty Images]

  • [Photo Credit: Getty Images]

  • [Photo Credit: Getty Images]

  • [Photo Credit: Getty Images]

  • [Photo Credit: Getty Images]

  • [Photo Credit: Getty Images]

  • [Photo Credit: Getty Images]

  • [Photo Credit: Getty Images]

  • [Photo Credit: Getty Images]

  • [Photo Credit: Getty Images]

  • [Photo Credit: Getty Images]

  • [Photo Credit: Getty Images]

  • [Photo Credit: Getty Images]

While technically not called “Young Hollywood,” the class of 1999 was the youngest crop of stars to grace the cover of Vanity Fair’s traditional Hollywood issue. Among the new faces featured were Kate Hudson, Julia Stiles and Leelee Sobieski. Over all, the issue had a good track record with a number of surprises to pop nearly a decade after appearing in the magazine.

The Highs: Monica Potter, who would pop with the Freddie Prinze Jr rom-com, Head Over Heels, before becoming the emotional center of NBC’s dramedy, Parenthood. A longterm investment turned out to be Norman Reedus, who after building buzz for The Boondock Saints became a fan favorite as Daryl on The Walking Dead.

The Lows: Missteps included Vinessa Shaw, who just picked up minor supporting roles in a string of films following Eyes Wide Shut, and Sobeiski, who started off promising but practically disappeared.

>>>Next: The Class of 2000

The Class of 2000

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Among the fresh faces featured in the class of 2000 were a number of teen film breakout stars, including Selma Blair, Jordana Brewster, Chris Klein, and Paul Walker. This group was the true definition of “Young Hollywood” at the time. The stars were in practically ever hit teen comedy, on every red carpet and collecting all the MTV Movie Awards. Yet, not all of them were able to remain relevant.

The Highs: Penelope Cruz went from It Girl to legitimate actress after she won an Oscar for Vicky Christina Barcelona. Paul Walker cemented his status as Hollywood’s most laid back actor and lead in the long-running Fast and Furious series before his death.

The Lows: As one of the freshest faces, Sarah Wynter was a relative unknown when she was featured in the issue and remained so even though she had recurring roles on 24 and Californication.

>>>Next: The Class of 2003

The Class of 2003

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In an issue dedicated to teen stars, Vanity Fair’s 2003 issue turned into the who’s who of the post-Disney and Nickelodeon world. Everyone from Lindsay Lohan to Aaron Carter were among the stars featured in the issue, “It’s Raining Teens!” Though, it wasn’t hardly raining — it was pouring. However, this class turned out to be filled with the most dysfunctional group of actors yet. Amanda Bynes (Twitter meltdowns), Aaron Carter (alcohol), Shia LaBeouf (arrested), Solange Knowles (elevator fight), and Lohan (rehab) all became examples of how not to behave.

The Highs: The cast of Harry Potter. Daniel Radcliffe, Rupert Grint and Emma Watson turned out to be the most stable and hardworking young stars of 2003. Both Radcliffe and Watson have made their mark in Hollywood by transforming into credible adult stars.

The Lows: Aside from the deliquents, some of the other misses included Alexis Bledel, Aaron Meeks, Christian Millian, Kyla Pratt, and Alexa Vega failed to live up to their promise.

>>>Next: The Class of 2008

The Class of 2008 Pt. 1

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The 2008 issue introduced America to a more stable crop of young actors. The cast of Gossip Girl, indie stars Olivia Thirlby and Josh Peck, and big screen breakouts Amanda Seyfried and Kristen Stewart defined “Bright Young Hollywood” with a renewed sense of focus on credible stars with big hits under their belts.

The Highs: Emma Stone went from budding star to A-List with parts in The Amazing Spider-Man, Crazy Stupid Love, and The Help. Other standouts included Kat Dennings who became the star of Two Broke Girls, Jonah Hill who has delivered hit after hit and Amber Heard, who

The Lows: Misfires turned out to be the now defunct Jonas Brothers, Summer Bishil and Jessica Szohr.

The Class of 2008 Pt. 2

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In an alternative to the Hollywood Issue, Vanity Fair gathered together the 10 Fresh Faces of 2008. These names weren’t necessarily “young” but they were certainly “fresh.” Ladies like Amy Adams, American Ferrera, Anne Hathaway, and Ellen Page transitioned out of the teen films into adult roles. Suddenly they were delivering on what the past several issues promised.

The Highs: Amy Adams turned out to be an Oscar favorite, picking up nomination after nomination.

The Lows: Jessica Biel went from star on the rise to Mrs. Justin Timberlake.

>>>Next: The Class of 2010

The Class of 2010

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Two years after “Bright Young Hollywood,” Vanity Fair followed up with a declaration, we were entering “A New Hollywood!” Among the stars represented were some alums of previous issues, including Seyfried, Stone, and Evan Rachel Wood. New entries included even newer stars, such as Abbie Cornish, Rebecca Hall, and Anna Kendrick.

The Highs: Carey Mulligan has turned out to be a reliable actress, starring in hit after Indie darling after Oscar favorite.

The Lows: Kristen Stewart only because of her affair with Snow White and the Huntsman director Rupert Sanders, which brought her career to a brief halt.

>>>Next: The Class of 2014

The Class of 2014

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While it’s too early to tell just where the class of 2014 will end up, there are a number of promising selections in the group. Among the breakout stars are Dylan O’Brien and Shailene Woodley.

The Highs: Woodley who is the star of Divergent and The Fault in Our Stars and O’Brien who is the current star of MTV’s hit series Teen Wolf.

The Lows: Too early to tell.