Skip To Content
    Posted on Jul 7, 2016

    21 Photos From The 1999 Teen Choice Awards That Will Make You Wish You Had A Time Machine

    It was the year of all your faves.

    1. NSYNC looked like a mess while posing on the red carpet with Gloria Estefan. (#NeverForget "Music of My Heart")

    Sgranitz / WireImage

    Was JC Chasez expecting it to rain?

    2. Pink showed up looking like a badass. 🙌

    Jim Smeal / WireImage

    3. While Freddie PrinzeJr. showed up in Larry King cosplay.

    Jim Smeal / WireImage

    4. Jennifer Love Hewitt posed with LFO on the red carpet...

    Sgranitz / WireImage

    In case you forgot (but, really how could you?) she was also the star of their "Girl On TV" music video.

    5. ...and she also wore a dress that EVERY girl wore to senior prom in 1999.

    Sgranitz / WireImage

    6. While Melissa Joan Hart appropriated a sari — but to be fair, so did everyone in the late '90s.

    Frank Trapper / Getty Images

    7. Blink-182 was still together!

    Barry King / WireImage

    Why couldn't they stay together for us kids?!

    8. Tyrese fixed his fly in the press room.

    Ron Galella / WireImage

    9. While Ashton Kutcher pulled his pants down to show off his Calvin Klein underwear.

    S. Granitz / WireImage

    10. Ashton also posed with 1999 "It Boy" Carson Daly!

    Jeff Kravitz / FilmMagic, Inc

    11. Jason Biggs and Alyson Hannigan had just starred in American Pie.

    Jeff Kravitz / FilmMagic

    12. Wilmer Valderrama looked excited to be there! Well, at least Mila Kunis did.

    Jim Smeal / WireImage

    13. Christina Aguilera was just becoming known 'cause of "Genie In A Bottle."

    Ron Galella, Ltd. / WireImage

    14. Luke Perry and Ian Ziering were still on Beverly Hills, 90210.

    Jeff Kravitz / FilmMagic, Inc

    Thankfully not still playing teenagers.

    15. 98 Degrees looked like Structure sales associates.

    Jim Smeal / WireImage

    16. Vitamin C was probably there to sing "Graduation (Friends Forever)."

    Ron Galella / WireImage

    17. Daisy Fuentes felt up Jordan Knight's pecs.

    Frank Trapper / Getty Images

    GET. IT. DAISY.

    18. Sandra Bullock and Matthew McConaughey were a thing.

    Vinnie Zuffante / Getty Images

    19. Britney Spears slayed on the red carpet dressed in pants made of old disco balls.

    Frank Trapper / Getty Images

    20. She even posed in a photo with Buffy herself, Sarah Michelle Gellar. #ICONIC

    Jeff Kravitz / FilmMagic, Inc

    21. And finally, Jennifer Lopez looked the SAME as she does now.

    S. Granitz / WireImage

    Nostalgia Trip

    Take a trip down memory lane that’ll make you feel nostalgia AF

    Newsletter signup form