14 Rolling Stone Covers That Immortalized 1999 In Pop Culture

Looking back at the people and things that mattered to us 15 years ago.

1. The Hello Nasty-era Beastie Boys ruled.

For the record, they ALWAYS ruled.

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2. Lauryn Hill ruled the world — or at least our CD walkman.

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3. Jennifer Aniston talked about being Brad Pitt’s girlfriend.

*Sigh* I guess she’s always had to talk about her love life. ¯\_(ツ)_/¯

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4. The most late ’90s thing ever made the cover: frosted tips!

Oh, Sugar Ray’s Mark McGrath made the cover, too.

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5. Britney Spears shocked everyone by posing in this iconic Lolita-esque shoot.

Even that Teletubby was shocked.

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6. We were introduced to chka-chka Slim Shady.

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7. The Backstreet Boys were “the new teen spirit.”

And Kurt Cobain rolled over in his grave.

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8. Angelina Jolie wasn’t just hot, she was also a “devil doll” — whatever that means.

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9. Somehow Jar Jar Binks was labeled a superstar?!

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10. Yeah baby, Mike Myers brought Austin Powers back.

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11. Ricky Martin got wet while talking about sex, love, marriage, and yoga.

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12. David Spade scored a cover and we all lost :(

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13. Brad Pitt proved he could look sexy even while dressed like a late 1960s housewife.

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14. And Nic Cage made the cover, unironically.

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