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

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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

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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