By Neia Balao
6:42am PST, Nov 23, 2020
Who can forget when Justiney — err, Justin Timberlake and Britney Spears — hit the red carpet at the 2001 AMAs in their coordinating denim looks? From Britney's floor-length patchwork jean dress to Justin's denim suit and cowboy hat, the chart-topping sweethearts definitely drew attention. This outrageous AMAs fashion moment happened just one year before their infamously messy breakup in 2002.
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One of the most memorable moments of the 2011 AMAs? When Justin Bieber and Selena Gomez made a rare red carpet appearance as a couple. While their relationship would go on to have its fair share of highs and lows, these two teens were young and in love back in the day. That evening, Justin was up for favorite pop/rock male artist.
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At the 1996 AMAs, Mötley Crue rocker Tommy Lee and then-wife Pamela Anderson — who was pregnant with son Brandon Thomas Lee at the time — hit the red carpet together.
Remember when these two dated? Charlize Theron attended the 1999 American Music Awards with Third Eye Blind singer Stephan Jenkins, whom she dated for three years until 2001. What we can't get over in this pic? Charlize's purple fur-trimmed jacket!
Beyonce attended the 2003 American Music Awards with baby sister Solange, whose discography includes 2016's "A Seat at the Table" and 2019's "When I Get Home." That year, Bey was up for three AMAs: favorite soul/R&B album, favorite female soul/R&B artist and fan's choice.
Once upon a time, John Legend and Chrissy Teigen were just dating! The beloved Hollywood couple is seen here at the 2010 AMAs a little more than a year before the "All of Me" hitmaker asked the model to be his bride while on holiday in the Maldives in 2011.
At the 2014 American Music Awards, former boybander Lance Bass hit the red carpet alongside his then-fiancé, actor Michael Turchin. The couple married less than a month later.
Back in the day, Kendall Jenner and Kylie Jenner were best known for their minor appearances on "Keeping Up With the Kardashians." Nowadays, they've both crafted impressive and lucrative careers as the world's highest paid model and a self-made beauty mogul billionaire, respectively. The Jenner sisters are seen here at the 2013 AMAs.
Talk about a "Party of Five" and "Brotherly Love" crossover! Jennifer Love Hewitt attended the 1996 American Music Awards with then-boyfriend Joey Lawrence. The couple, however, called it quits that same year.
Admit it, you couldn't get enough of MTV's "Newlyweds: Nick and Jessica." Nick Lachey and Jessica Simpson attended the 2000 American Music Awards and looked absolutely smitten with one another. They got engaged two years later in October 2002.
Another unforgettable duo? "High School Musical" co-stars Vanessa Hudgens and Ashley Tisdale, who attended the 2006 American Music Awards together (in coordinating white dresses, no less). Their breakout film had debuted on the Disney Channel just 10 months prior.
The year was 2012, and Jordin Sparks and Jason Derulo attended the American Music Awards together. But their love didn't last: After three years of dating, they called it quits in 2014.
"Beautiful Soul" singer Jesse McCartney once dated "Arrow" actress Katie Cassidy (she even starred in his music video for "She's No You"!). They hit the red carpet together at the 2005 American Music Awards. Alas, all good things must come to an end — their romance, which lasted just over two years, fizzled out in 2007.
Enrique Iglesias, who was nominated for favorite Latin artist at the 2000 American Music Awards, attended the show with then-rumored girlfriend Shannon Elizabeth. The "American Pie" actress starred as the romantic interest in Enrique's video for "Be With You" in 2001.
We're so happy Ryan Sutter accepted her final rose! Trista Rehn — the first star of "The Bachelorette" — attended the 2003 AMAs with then-fiancé Ryan. The reality television pair — who are still together today! — married a month later in December 2003.
Some couples are easier to forget than others… like country star LeAnn Rimes and "10 Things I Hate About You" actor Andrew Keegan, who dated from 1998 to 2001. Their romance reportedly fizzled out after Andrew became interested in "Coyote Ugly" star Piper Perabo, whose singing voice was replaced by LeAnn's in the film. Yikes.
Former "Hannah Montana" star Miley Cyrus posed for photos on the red carpet with mom Tish Cyrus ahead of the 2007 American Music Awards. Five days after the award show, Miley celebrated her Sweet 16 birthday.
Seeing double! Of course "Sister, Sister" stars Tia Mowry and Tamera Mowry were each other's dates! The adorable twins donned very '90s gowns for the 1999 American Music Awards.
Blink-182 drummer Travis Barker attended the 2005 American Music Awards with his then-wife, Miss USA 1995 Shanna Moakler, who was pregnant with their second child, Alabama, at the time. The pair's love didn't last forever — they divorced in 2008.
While their love is definitely stronger than ever, there was a time when Faith Hill and Tim McGraw could be considered newlyweds! The country darlings are seen here at the 1997 American Music Awards a little more than three months after they tied the knot. That evening, Faith — who was pregnant with their first child at the time — was up for favorite female country artist.
Dua Lipa and Anwar Hadid had only been dating for only a few months when they attended the 2019 American Music Awards, where Dua performed her hit single "Don't Start Now."
An iconic duo if we've ever seen one: Daryl Hall and John Oates, who are famously known for '80s hits like "You Make My Dreams Come True," "Private Eyes" and "Kiss on My List," attended the 2003 American Music Awards together in absolute style (we love a coordinating black-jacket moment).
"Robot Chicken" co-creator and voice actor Seth Green showed up to the 2009 American Music Awards with actress-model Clare Grant. They met in 2006 and went on to tie the knot in 2010.
We love a sibling moment! "The Boy Is Mine" hitmaker Brandy, who was nominated for favorite female soul R&B artist that year, attended the 1997 American Music Awards with her younger brother, Ray J.
"Sabrina the Teenage Witch" and "Drive Me Crazy" star Melissa Joan Hart was heart-eyes for her then-fiancé, musician Mark Wilkerson, at the 2003 American Music Awards. Six months later, they tied the knot.
At the 2018 American Music Awards, "How I Met Your Mother" actress Cobie Smulders attended with her husband, "Saturday Night Live" star Taran Killam. The pair married in 2012 and share two daughters.
Before she went on to become a presenter on E!'s "Fashion Police" and appear on shows like "Dancing with the Stars," "Australia's Got Talent" and "Project Runway," Kelly Osbourne and younger bro Jack were stars on the MTV reality show "The Osbournes." The English siblings are seen here at the 2003 AMAs.
