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.