14 Rolling Stone Covers That Immortalized 1999 In Pop Culture

14 Rolling Stone Covers That Immortalized 1999 In Pop Culture

Looking back at the people and things that mattered to us 15 years ago. posted on July 22, 2014, at 8:30 p.m.

1. The Hello Nasty-era Beastie Boys ruled.

For the record, they ALWAYS ruled.

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

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

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

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

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

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

Even that Teletubby was shocked.

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

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

And Kurt Cobain rolled over in his grave.

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

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

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

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

12. David Spade scored a cover and we all lost 😦

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

14. And Nic Cage made the cover, unironically.

And Nic Cage made the cover, unironically.

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