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Can You Guess the Winners at the First Teen Choice Awards 20 Years Ago?

These were the stars taking over in 1999.

Twenty years ago, we connected to the the internet via dial-up, wore tons of choker necklaces, and were glued to the first-ever Teen Choice Awards. The surfboard-centric event saw performances from Britney Spears and *NSYNC, and multiple prizes were heaped upon the stars of The WB. Seems like yesterday, right? To find out how well you remember late '90s pop culture, take this quiz on the Teen Choice Awards winners from the inaugural ceremony in 1999.

Yes, it's time to brush up on your Backstreet Boys and get ready to find out who was the year's definitive "female hottie," the most beloved model, the voice behind the song of summer, and so much more. Much like the stars of Dawson's Creek, we know you don't wanna wait, so let's get started!

Who won the award for Choice Female Artist?

microphone, 1999 teen choice awards

Hint: This singer also starred in a popular live-action Disney princess movie remake.


brandy teen choice awards 1999

After taking on the lead role in the Whitney Houston-produced movie Cinderella, Brandy released her second studio album, Never Say Never, in the summer of 1998. Its chart-topping hits like "Have You Ever?" and "The Boy Is Mine" with Monica helped her win this award at the first Teen Choice Awards the following year.

Which band won Choice Rock Group?

rockers at rock concert

Hint: This iconic '90s trio is best known for their hit single about the smaller things in life.


blink 182 teen choice awards 1999

Alternative rock group Blink-182 entered the mainstream with the release of their third studio album, Enema of the State, in the summer of 1999. The newfound fame earned the band the surfboard for Choice Rock Group at the 1999 Teen Choice Awards. With breakthrough bangers like "What's My Age Again?" and "All the Small Things," the album went on to sell more than 15 million copies worldwide.

Who won Choice Female Hottie?

vintage mirror, 1999 teen choice awards

Hint: This star later became famous for her ability to connect with the supernatural.

Jennifer Love Hewitt!

jennifer love hewitt, teen choice awards 1999

Shortly after stealing hearts in the 1998 high school comedy Can't Hardly Wait, Jennifer Love Hewitt walked away with the award for Choice Female Hottie at the first Teen Choice Awards—and hardly anyone was surprised. After all, who could forget her iconic entrance as Amanda Beckett during the movie's massive graduation party?

Who took home the Choice Music Album award?

piles of cds on the table, 1999 teen choice awards

Hint: This group's first hit was titled "I Want You Back."


nsync teen choice awards 1999

During the era of fanny packs and frosted tips, *NSYNC was the boy band to listen to—and given the success of their self-titled debut album in 1997, it's no surprise that they took home the Choice Music Album award at the first Teen Choice Awards ceremony.

Which Hollywood star walked away with the award for Choice Hissy Fit?

close up of the hands of a couple arguing with woman pointing finger at man, etiquette mistakes

Hint: This superstar's breakthrough role was opposite Keanu Reeves.

Sandra Bullock!

sandra bullock teen choice awards 1999

Before she was the ultimate mother figure in The Blind Side or scaring audiences in Bird Box, Sandra Bullock was playing the dysfunctional Sarah Lewis in the 1999 rom-com Forces of Nature, alongside Ben Affleck. The movie may not have won critics over, but teens loved Bullock's performance enough to grant her the Teen Choice Award for Choice Hissy Fit.

Who won Choice Love Song?

Couple Holding Hands

Hint: Before Clueless, Alicia Silverstone was known for appearing in multiple music videos for this artist.


aerosmith teen choice awards 1999

Though Aerosmith has been a notable name in rock music since they formed in the early 1970s, they were still going strong in the late 1990s. Their hit "I Don't Won't to Miss a Thing," from the feature film Armageddon—which starred Steven Tyler's daughter, Liv Tyler—earned them a place in the hearts of teenagers everywhere. They even took home the Teen Choice Award for Choice Love Song.

Who was named Choice Model?

model studio, 1999 teen choice awards

Hint: This stunner knows the art of smiling with her eyes.

Tyra Banks!

tyra banks 1999 choice awards

Tyra Banks began modeling when she was just 15 years old—and by the time she was in her 20s, she was gracing the covers of Sports Illustrated and GQ as well as working as a Victoria's Secret model. So it's no surprise that Banks won the first Teen Choice Award for Choice Model in 1999.

Who won Choice Breakout Group?

concert, 1999 teen choice awards

Hint: This former group featured none other than Jessica Simpson's ex.

98 Degrees!

98 degrees teen choice awards 1999
Featureflash Photo Agency /

Nick Lachey got his start alongside brother Drew in the boy band 98 Degrees. And a year after they released their second studio album, 98 Degrees and Rising, in 1998, the group was honored with the first Teen Choice Award for Choice Breakout Artist.

Who was behind the Choice Song of the Summer?

pool dj, 1999 teen choice awards

Hint: This age-defying superstar is proud to call the Bronx her home.

Jennifer Lopez!

jennifer lopez 1999 teen choice awards

Jennifer Lopez made waves with her debut single, "If You Had My Love," which she released in 1999. Thanks to its success, J-Lo became the first artist since Britney Spears to top the Billboard Hot 100 with their first single. And her track also earned her the Choice Song of the Summer award at the Teen Choice Awards that year.

Who won Choice Pro Wrestler?

wrestling ring

Hint: This professional wrestler can be found in a lot of Adam Sandler movies.

"Stone Cold" Steve Austin!

steve stone cold austin, 1999 teen choice awards

Before he was known as "Stone Cold," wrestler Steve Austin was performing under the name "Stunning" in the early '90s. But by 1999, he had ditched his former moniker for "Stone Cold" and was taking home awards like the 1999 Choice Pro Wrestler award at the Teen Choice Awards.

Which star was named Choice TV Actress?

person turning off tv

Hint: This actress is can slay all day.

Sarah Michelle Gellar!

sarah michelle gellar teen choice awards 1999

Twenty years ago, Sarah Michelle Gellar was busy slaying vampires on Buffy the Vampire Slayer. And by the time the Teen Choice Awards aired in 1999, she was also blowing up the big screen with roles in I Know What You Did Last Summer, Scream 2, and Cruel Intentions. Her myriad roles landed her a place in teens' hearts all across America—and ultimately secured her the first-ever Choice TV Actress award.

Which on-screen pair gave us the Choice Sexiest Love Scene?

feet in bed, best sex positions

Hint: This actress was also known for her lead role in Josie and the Pussycats.

Rachael Leigh Cook and Freddie Prinze Jr.!

rachael leigh cook, teen choice awards

At the 1999 Teen Choice Awards, Rachael Leigh Cook won Choice Sexiest Love Scene alongside Freddie Prinze Jr. for their work in She's All That. The movie stars Cook as a socially awkward teen who, in the process of getting a Cinderella-esque makeover, falls for the popular soccer captain (played by Prinze Jr.).

Who had the Choice Single of the Year?

radio station

Hint: This singer got their start early as a cast member on The Mickey Mouse Club.

Britney Spears!

britney spears teen choice awards

In the late 1990s, Spears was the "Teen Queen," as Rolling Stones aptly named her. She released her debut album, …Baby One More Time, at the beginning of 1999, and its title track was later released as the lead single. Not only did this catchy song win Spears the first Choice Single of the Year award, but music critic Amanda Murray noted on Sputnikmusic that it "will be long remembered as one of the cornerstones of pop music in general." All hail Queen Britney!

Who was the Choice Female Athlete?

gold medal on the table,

Hint: At the age of 15, this athletic superstar became the youngest winner of an individual medal at the 1998 Nagano Olympic games.

Tara Lipinski!

tara lipinsky 1999 teen choice awards

Tara Lipinski took home the gold at the 1998 Winter Olympics at just 15 years old. And given how monumental her win was, it's no surprise that the skater also took home the award for Choice Female Athlete at the inaugural Teen Choice Awards the following year.

Which show won Choice TV Drama?

save 40 percent of your paycheck

Hint: This series made one of Tom Cruise's former wives a household name.

Dawson's Creek!

dawsons-creek-meredith-monroe 1999 teen choice awards

The world was introduced to Dawson's Creek in 1998, and it became so beloved that it not only took home the first ever Teen Choice Award for Choice TV Drama, but also ran with high accolades through 2003. And for more beloved television shows, check out The 50 Best One-Season TV Shows in Television History.

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Kali Coleman
Kali Coleman is a Senior Editor at Best Life. Her primary focus is covering news, where she often keeps readers informed on the ongoing COVID-19 pandemic and up-to-date on the latest retail closures. Read more
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