11 Riveting Teen People Covers That Immortalized 1999

A look back to 15 years ago when all we cared about were frosted tips and crop tops.

1. December 1998/January 1999: Jennifer Love Hewitt and Brandy assumed people still cared about what they did last summer.

PLUS: SUGAR RAY! They had important news about SUGAR RAY.

2. February 1999: Justin Timberlake’s ramen noodle hair and the rest of NSYNC gave their most intimate interview ever.

Also, I believe this is when we first began asking questions about Chris Kirkpatrick’s hair.

3. March 1999: Alicia Silverstone opened up about her past problems — which I think was code for regretting her appearance in Batman and Robin.

4. April 1999: Lauryn Hill opened up about fame, all while rocking a ribbed turtleneck, an essential late-’90s fashion staple.

Also, we learned what was really going down in raves. Spoiler alert: DRUGS.

5. May 1999: Drew Barrymore brought assistant manager at the Gap realness to her cover shoot.

Plus they totally teased us with a very Cosmo article title, “Sex on the Job”, but it was about sexual harassment.

6. June/July 1999: In news to make you feel old: Nick Carter, Monica, and Britney Spears were all stars under 21.

7. August 1999: Will Smith tried to make Wild Wild West happen.

8. September 1999: 98 Degrees gave an exclusive interview, which I assume was about tank tops and frosted tips.

9. October 1999: Gotta be honest, Sarah Michelle Gellar looked kinda sleepy on the cover. Maybe she was daydreaming about how she would change the world.

10. November 1999: Jennifer Love Hewitt made an important style choice by wearing an oh-soooo-cute-then crop top with a long skirt on her cover.

11. December 1999/January 2000: Christina prepared us for the year 2000, by looking like she was wearing 1960s wallpaper.

Plus, we got “up close and very personal” with LFO and it was probably the last time we ever cared to.

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