28 Celebrity Moments From The 1999 Teen Choice Awards

A look back 15 years ago, to the very first Teen Choice Awards.

1. Pink arrived looking fierce and rocking that late ’90s cowboy hat trend.

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2. While Melissa Joan Hart showed up wrapped in a sari.

WireImage/ SGranitz

3. Vitamin C was not there to smile.

WireImage Ron Galella, Ltd.

C’mon Vitamin C, put a smile on your face!

4. Speaking of not smiling, Wilmer Valderrama looked like was he thrilled to be there, while his That’s ’70s Show co-star Mila Kunis looked adorable.

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5. Ashton Kutcher looked like he came in his That ’70s Show character, Kelso.

WireImage Ron Galella, Ltd.

6. NSYNC showed up in a whole lot of synthetic shiny clothing and frosted tips.

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While Chris Kirkpatrick showed up with that weird pineapple hairstyle.

7. America’s third favorite boy band, 98 Degrees, arrived in coordinating outfits.

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8. Tatyana Ali looked pretty in lavender.

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9. Alyson Hannigan looked like she was channeling Garbage’s Shirley Manson.

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10. And she took a moment to pose with her American Pie co-star Jason Biggs.

FilmMagic/ Jeff Kravitz

11. Steven Tyler was there too (along with his Aerosmith bandmate Joe Perry), bringing “cool mom” vibes to the show.

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12. While Freddie Prinze Jr. brought some goofy dad realness.

WireImage/ Jim Smeal

13. Christina Aguilera somehow managed to work both a large belly chain and pink pleather cheetah print skirt.

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14. Monica sparkled (literally, she looks she rolled around in gold glitter).

WireImage/ Jim Smeal

15. While her “Boy Is Mine” duet partner, Brandy, looked chic in white.

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16. Sandra Bullock and her then-boyfriend Matthew McConaughey were flirtatious backstage.

WireImage/ Jim Smeal

17. Tyra smized for her life.

WireImage Jim Smeal

18. TLC (or at least two-thirds of them) looked thrilled to be there.

FilmMagic, Inc/ Jeff Kravitz

19. Beverly Hills, 90210’s Luke Perry and Ian Ziering were probably there to receive a lifetime achievement award for playing teenagers for like 15 years.

FilmMagic, Inc/ Jeff Kravitz

20. Jennifer Lopez looked flawless (like always).

WireImage/ Barry King

Also, how has J.Lo not aged in 15 years?!

21. Sarah Michelle Gellar looked kick ass (of course).

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22. Tyrese zipped up his pants after almost flashing the camera.

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23. Rachel Leigh Cook was all that.

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24. Jordan Knight was there after reclaiming teen idol status with his solo hit “Give To You.”

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25. Blink-182 brought the love.

WireImage SGranitz

26. While Britney Spears brought pink disco ball pants.

Getty Images/ Brenda Chase

27. Jennifer Love Hewitt, the unofficial teen queen of 1999, showed up in every late ’90s girl’s dream prom dress.

WireImage/ Ron Galella, Ltd.

28. And she reunited on the red carpet with LFO, whose video for “Girl on TV” she starred in.

WireImage/ SGranitz

Relive the magic (?) of “Girl On TV”:

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