Flashing Back To The Most Popular Celebrities At The 1999 American Music Awards

It’s strange to think that the ’90s were decades ago. While to some extent the decade seems like it happened yesterday, certain trends give away the time that has flown by. For example, remember when Will Smith was known more for his music than he was for his acting? And whatever happened to the adorable and talented singer Brandy? Long gone are the days when Britney Spears was America’s sweetheart. All of these stars and more were at the 1999 AMAs, and you may be shocked to see how different they looked back then.

The Backstreet Boys In Their Prime

The Backstreet Boys pose together.
Ron Galella, Ltd./Ron Galella Collection via Getty Images
Ron Galella, Ltd./Ron Galella Collection via Getty Images

The natural place to start when looking at the late ’90s is with the boy band that just about every teenage girl was obsessed with. The Backstreet Boys were quick to rise to fame in the mid-’90s. By 1999, their third album had been their biggest one yet.

They are known today for being the best-selling boy band of all time and have shattered the record for albums to reach the top 10 as far as boy bands go. Best of all, they’re still on the charts, hitting number one in 2019 for their album DNA.

KISS Being Eccentric As Ever

Rockband KISS poses in full makeup.
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SGranitz/WireImage/Getty Images

KISS is one of those rare rockbands whose music and style just won’t fade. Formed in the early ’70s, they are one of the few bands to continue performing for decades. However, the band did take a momentary hiatus from their lavish makeup.

From the mid-eighties to the mid-nineties, the band rid themselves of the makeup and costumes that made them so recognizable. By the late ’90s, they were back to their eccentric, early ’70s ways. The band has made it on several lists ranking the best bands of all time.

Celine Dion For The Win

Celine Dion holds three AMAs.
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Ke.Mazur/WireImage/Getty Images

While Celine Dion was a Canadian teen star, it wasn’t until the ’90s that Americans really began to grasp how incredible this singer is at her job. By the mid-’90s she was ranking in the top selling albums in both English and French.

It was also during this decade that one of her most trademark songs “My Heart Will Go On” came out. As you can see, she’s struggling to juggle her three AMAs. However, Celine was just warming up. A decade later, she would embark on one of the highest-grossing concert tours of all time.

Snoop Dogg Looking Too Cool For School

Snoop Dogg wears a straight face and hold his arms open wide while being photographed.
Ron Galella, Ltd./Ron Galella Collection via Getty Images
Ron Galella, Ltd./Ron Galella Collection via Getty Images

While it seems like rap music never existed without Snoop Dogg, in reality it wasn’t until the ’90s that he hit the scene. Discovered by the renouned Dr. Dre, Snoop Dogg released his debut album in 1993.

By 1999, he looked like he’d been in the limelight forever. He had signed with a new record label and put out his fourth album. Little did anyone know, in 2012 Snoop would step back from rap in order to pursue reggae music under the new name Snoop Lion.

The Dixie Chicks Being Cute As A Button

The Dixie Chicks pose together.
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Though the Dixie Chick had formed a decade prior to the ’99 award ceremony, it wasn’t until ’98 that the women finally found commercial success. The ladies from Dallas, Texas spent years performing at small venues before getting picked up by a major label.

The three singles that put them on the map in 1998 were “There’s Your Trouble,” You Were Mine,” and “Wide Open Spaces.” However, the recognition they had recieved by the time they landed at this award show was minimal compared to the more than a dozen Grammys they’ve racked up since.

Carmen Electra Looking Electrifying As Ever

Carmen Electra smiles while wearing a form-fitting gray dress.
Jim Smeal/Ron Galella Collection via Getty Images
Jim Smeal/Ron Galella Collection via Getty Images

While Carmen Electra is known nowadays for her acting, she actually began her career as a singer. In fact, it was the legendary Prince who produced her breakout album. By the late ’90s, she gained notoriety as a dream girl on the show Baywatch.

It was also around this time that Electra began modeling, further popularizing her image. Though you wouldn’t guess it based on this photo alone, she had just lost both her mother and her sister the year before and was approaching a divorce. The resilient celebrity didn’t let her personal life get in the way of her career, and is still acting today.

The Mowry Twins Blowing Kisses

Tia and Tamera Mowry blow kisses to the camera.
Patrick McMullan/Getty Images
Patrick McMullan/Getty Images

Tia and Tamera Mowry were two of the most admired faces of Disney Channel’s television shows, which expanded into the adolescent territory in the ’90s. As the stars of the show Sister, Sister, the twins spent their teen years performing as the sassy twins you had to love.

This year marked the finale of their hit show. However, they would go on to star with their little brother in the Disney film Seventeen Again the following year. The twins have dabbled in television ever since, even landing their own reality show.

NSYNC Was A Rising Star

The group NSYNC poses together while holding an AMA award.
Frank Trapper/Corbis via Getty Images
Frank Trapper/Corbis via Getty Images

NSYNC was like the little brother of the Backstreet Boys. Not only were they neck and neck with the Backstreet Boys for the top boy band title of the ’90s, but they also formed in the same exact town as their rivals: Orlando, Florida.

Though they hit the scene three years after the Backstreet Boys, NSYNC was quick to crank out hit after hit. This shouldn’t come as a surprise considering the fact that the band also had the same manager as the Backstreet Boys, Johnny Wright.

98 Degrees Was Hotter Than Ever

The group 98 degrees poses for a photo.
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Long before Nick Lachey was featured on reality TV as the husband (now ex-husband) of Jessica Simpson, he was in a vocal group called 98 Degrees. The group also included his brother Drew, the shortest of the group, and friends Jeff Timmons and Justin Jeffre.

In an effort to be discovered, the group snuck into a Boys II Men concert where they sang live for a radio station covering the concert, attracting the attention of a music manager. While their fame was short-lived, in 1999 they were still hot off a collaboration with Stevie Wonder for the movie Mulan, a song called “True to Your Heart.”

Whitney Houston And Friends

Babyface, Whitney Houston, and Wyclef Jean pose together for a photo.
Ron Galella/Ron Galella Collection via Getty Images
Ron Galella, Ltd./Ron Galella Collection via Getty Images

That smiling face in the center belongs to the late and great Whitney Houston. Her fame exploded in the mid-’80s, but her acting career perked up in the ’90s. Her first starring role was in The Bodyguard, which featured her iconic song “I Will Always Love You.”

A couple of years later, Houston starred in Waiting to Exhale, that soundtrack of which was written and produced by Babyface, the gentleman to the left. To the right is Wyclef Jean, a rapper, musician, and actor who broke out with his solo career in 1997 and cowrote Houston’s song “My Love Is Your Love.”

Extra Sweet Brandy

The singer Brandy smiles for a photo.
Ron Wolfson/Getty Images
Ron Wolfson/Getty Images

By the mid-’90s, Brandy was a teen idol who was compared to Aaliyah, Janet Jackson, and Mary J. Blige. Her soft but raspy voice was easy to recognize and her look was both innocent and approachable. Her first album earned several awards and had a handful of hits such as “Baby.”

Brandy’s close relationship with Whitney Houston, her idol, blossomed at the end of the decade and earned her the lead in Rodger and Hammerstein’s made-for-TV movie, Cinderella. Brandy has since been in and out of the spotlight and made her debut on Broadway in 2015 as the lead in the musical Chicago.

Goo Goo Dolls Were All That

Members of the band Goo Goo Dolls pose with slight smirks.
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Goo Goo Dolls had released several albums by the late ’90s, but it was singles like “Name” and “Slide” that made them a commercial success. “Iris” remained on the Billboards for almost a solid year, which explains why if you’ve heard it, it’s probably already stuck in your head.

Their popularity landed them a guest spot on popular ’90s shows like Charmed and Beverly Hills, 90210. The band continued to have a steady stream of success after the ’90s and is still touring and releasing new albums.

Paula Abdul Was An Idol Before Idol

Paula Abdul poses in a sleek, pink dress.
Jim Smeal/Ron Galella Collection via Getty Images
Jim Smeal/Ron Galella Collection via Getty Images

Long before Paula Abdul was a judge on American Idol, she was a singer and dancer. She was pegged by the famed Jackson family during a Lakers game while cheerleading. After building her resume as a celebrity choreographer, she turned to singing.

She had two successful albums in the ’90s, all while continuing to choreograph music videos and movies. In 1995, she also released a dance workout video. Abdul has since appeared in various competition shows. Her most recent single was “I’m Just Here for the Music,” which made it onto the Billboard chart in 2009.

Will Smith Was At The Top Of His Music Game

Will Smith smiles while holding up two AMAs.
GERARD BURKHART/AFP via Getty Images
GERARD BURKHART/AFP via Getty Images

Will Smith began his career as a rapper in the ’80s, but it wasn’t until The Fresh of Bel-Air that his commercial fame erupted. Throughout the ’90s, Smith starred in the show while establishing himself as a rising Hollywood actor.

In 1997, Smith returned to his music with the successful hit “Men in Black,” which accompanied the movie of the same name. He also released his first solo album, Big Willie Style, which included “Gettin’ Jiggy Wit It,” Smith’s first song to hit number one on the Billboard Hot 100.

Third Eye Blind And Their Famous Fan Girl

Rockband Third Eye Blind poses in front of actress Charlize Theron.
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SGranitz/WireImage/Getty Images

Shortly after forming in San Francisco, Third Eye Blind became a commercial success. Just think of the song “Semi-Charmed Life” and you’ll realize how much they infiltrated the ’90s culture. In 1999, the band had released their second album, Blue, which was nearly as successful as the first had been.

As if their smash hits weren’t fame-inducing enough, the lead singer also dated actress Charlize Theron. It was in the late ’90s that Theron’s success was just starting to take off. Unfortunately, the two split in 2001; it’s alleged that the band’s third album is in large part about her.

The Goofy Wayans Brothers

Marlon and Shawn Wayans grip one anothers hands while posing for a photo.
Ron Galella, Ltd./Ron Galella Collection via Getty Images
Ron Galella, Ltd./Ron Galella Collection via Getty Images

Marlon Wayans and Shawn Wayans are the two youngest of several Wayans in the entertainment industry. While you may recognize them for their hilarious acting roles, such as the two leads in the movie White Chicks, they are also writers and producers.

In the late ’90s, the brothers were mostly known for starring in the comedy show The Wayans Bros. which aired from 1995 until 1999. Prior to that, they performed in the popular sketch show In Living Color. The brothers have written, produced, and starred in a handful of films since.

Britney Spears Looking Angelic

Britney Spears has crimped hair framed by a sparly headband while wearing a pink dress.
Ron Galella, Ltd./Ron Galella Collection via Getty Images
Ron Galella, Ltd./Ron Galella Collection via Getty Images

Britney Spears was initially rejected from The Mickey Mouse Club for being too young but landed her spot a few years later after appearing in several commercials. By 1997, Britney Spears was ready to embark on a solo career. Ironically, she was rejected by labels who doubted she would be a success without a group.

In 1999 her debut album …Baby One More Time landed at number one on the Billboard 200. The following year, her album Oops!… I Did It Again solidified her commercial success. She gradually moved away from her innocent look and became the Britney we know today.

The Untouchable Sugar Ray

The member of Sugar Ray pose next to one another and the lead singer points to the camera.
Ron Galella, Ltd./Ron Galella Collection via Getty Images
Ron Galella, Ltd./Ron Galella Collection via Getty Images

The ’90s wouldn’t have been the same without the fun-loving song “Fly” by rockband Sugar Ray. Given the hits pop sound, it’s hard to believe that Sugar Ray started out as a nu metal band in the ’80s. By the ’90s, the had adapted to their softer, catchier style.

In 1999, the band responded to the assumption that “Fly” would be a one hit wonder by titling their next album 14:59, a reference to their presummed 15 minutes of fame. They beat the odds with more hits such as “Someday” and, in their following album, “When It’s Over.”

Everclear Was Making Moves

The three musicians in the rockband Everclear pose next to one another.
Ron Galella, Ltd/Ron Galella Collection via Getty Images
Ron Galella, Ltd/Ron Galella Collection via Getty Images

Everclear knocked it out of the park in the ’90s with all three of their first albums reaching platinum status. However, their success came after a host of ups and downs, including frontman Art Alexakis forming the bankrupted Shindig Records.

Nevertheless, the band found commercial success, largely due to their 1996 hit “Father of Mine.” Though their songs didn’t make it to the very top of the Billboard charts, the band still won the Billboard’s Modern Rock Band of the Year Award in 1998.

Cher Looking Way Too Good For This

Cher wears an odd headpiece and has her arms crossed and a straight face.
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SGranitz/WireImage/Getty Images

Though Cher was in her fifties during the ’90s, her fame was far from reaching its peak. In fact, she was back on top in 1998 for her upbeat album Believe, which made her one of the first artists to successful utilize Auto-Tune.

The album’s title track was popular across the world, reaching number one in nearly two dozen countries. On top of that, Cher had established herself as an actress, starring in movies like Moonstruck and Mermaids. The superstar is still on top of the world today, working on new albums and an autobiography.