back to top

Why 1999 Was The Best Year Ever

Life was just more awesome then.

Posted on

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.

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.

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.

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.


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.

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.

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.

"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.


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.

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.


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.'

"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.