1. Chris Rock hosted the best MTV Video Music Awards
Let’s see: Diana Ross jiggled Lil Kim’s boob (pictured), Lauryn Hill won Video of the Year, Afeni Shakur and Voletta Wallace presented the award for Best Rap Video, and Britney Spears and ‘N Sync performed for the first time.
2. 10 of the greatest teen movies were released
All the teen stars appeared in all the teen movies that year, including 10 Things I Hate About You, American Pie, Cruel Intentions, Drive Me Crazy, Drop Dead Gorgeous, Election, Jawbreaker, Never Been Kissed, She’s All That, and Varsity Blues.
3. TLC returned
Five years after the release of CrazySexyCool, TLC returned with a number one album, FanMail, which included major radio hits such as ‘No Scrubs’ and ‘Unpretty.’ The band was everywhere that year and picked up several awards along the way.
4. Latin music invaded radio
Ricky Martin led the way for latin influence in pop music with the wildly successful English-language self-titled debut. Marc Anthony, Enrique Iglesias, and Santana all had major hits in the same year that Jennifer Lopez (pictured) officially added “slash singer” to her resume.
5. Haley Joel Osment saw dead people
The Sixth Sense was released in theaters, launching a craze for twist-endings in movies while giving us one of the best lines in pop culture delivered by a then-adorable child actor.
6. Brandi Chastain stripped on field
During the FIFA Women’s World Cup final against China, U.S. soccer player Brani Chastain scored the winning penalty kick and subsequently whipped her jersey off during an on-field celebration.
7. Gwyneth won the Oscar
Before she was the GOOP, Gwyneth earned critical acclaim for her turn as Viola De Lesseps in Shakespeare in Love. She eventually won the Oscar for Best Actress and gave a touching acceptance speech.
8. “The West Wing” debuted
On September 22nd, audiences sat down to watch the premiere of the Aaron Sorkin drama, The West Wing, which would go on to air for seven seasons and revive Rob Lowe’s acting career. Dulé Hill also appeared in the teen flick, She’s All That.
9. David Cone pitched a perfect game
On July 18th, David Cone pitched a perfect game against the Montreal Expos in the last no-hitter to date by a Yankee.
10. Susan Lucci finally won that damn Emmy
After 19 nominations, the star of All My Children finally took home the statue.
11. Britney bared all on the cover of Rolling Stone
1999 saw the debut of several teen pop stars, including Christina Aguilera and Jessica Simpson, but none of them rocketed to the top like Britney Spears did. Already scoring with ‘…Baby One More Time,’ the singer exploded when she appeared on the cover of Rolling Stone.
12. Bill Clinton was acquitted
After lengthy impeachment proceedings regarding Bill Clinton’s involvement in the Monica Lewinsky scandal, the president was acquitted of all charges of perjury and obstruction of justice.
13. “The Last Supper” was restored
After 21 years of restoration, Leonardo da Vinci’s The Last Supper was put back on display for the public.
14. Destiny’s Child still had its original lineup
The group released their sophomore album, The Writing’s On The Wall, and apparently LaToya Luckett and LaTavia Roberson should have seen the signs. Less than a year later, the two were infamously replaced in the music video for ‘Say My Name.’
15. Napster launched
Napster revolutionized the Internet and changed the way consumers get music. However, Napster tried to go legal and hasn’t been the same since. :(
16. “Family Guy” premiered
The show premiered after the Super Bowl XXXIII on January 31st. Though it was canceled during its initial run, the show became a cult hit on DVD and was eventually relaunched on FOX.
17. Everyone joined a fight club
Fighting never looked so sexy or was so secretive.
18. Neo took the red pill
The Matrix led us all to question our “reality” in this sci-fi epic.
19. Kiernan Shipka was born
The child star of Mad Men, Miss Sally Draper, was born. TV was forever thankful.