Stars at their very first MTV VMAs | Gallery

Recognize this young lady? It’s Ariana Grande on the red carpet at her very first MTV Video Music Awards back in 2013. The pop star rocked a floral minidress by Kenley Collins but was without her now-signature ponytail that night. Ari sang “Baby I” and “The Way” at the pre-show that year. In honor of the 2020 MTV VMAs on Aug. 30, Wonderwall.com is bringing you photos of more stars on their very first Video Music Awards nights. Keep reading for more…

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The MTV Video Music Awards were held in South Florida in 2005 — and Rihanna arrived ready for the Miami heat! The star rocked a crop top, white jeans and heels at her first VMAs outing where she also performed her first hit, “Pon de Replay,” at the preshow. 

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Beyonce attended her very first MTV VMAs 20 years ago! Yep, the superstar attended as a member of Destiny’s Child with fellow members Kelly Rowland and Michelle Williams then took home a Moonman for best R&B video for “Say My Name.” 

Drake performed at his inaugural VMAs in 2010. The rapper, who was up for two Moonmen, delivered his hit “Fancy.”

The Backstreet Boys arrived at their first VMAs in 1998. That year, the guys won best group video for “Everybody (Backstreet’s Back).” 

In 2009, Lady Gaga attended her very first VMAs. The pop star arrived wearing Jean Paul Gaultier and left with three Moonmen: She won for best new artist and her “Paparazzi” video won for best special effects and best art direction.

1999 was the first year the MTV VMAs were blessed with Britney Spears’ presence. She performed that night with then-boyfriend Justin Timberlake’s group *NSYNC.

The same year Britney Spears attended the VMAs for the first time, so did her fellow pop star Christina Aguilera. Xtina was on hand to present best rock video with Tommy Lee. 

Kanye West had a very special date for his first time at the MTV VMAs — his mother, Donda! The rapper brought his mom along to the 2004 ceremony, where he performed a medley of his tunes: “Jesus Walks,” “All Falls Down” and “Through the Fire.” 

Jennifer Lopez’s first time at the MTV Video Music Awards was more than two decades ago! She attended the 1998 ceremony as a presenter, as her debut album “On the 6” wouldn’t be released for another year.

*NSYNC’s first time at the VMAs took place in 1999 when they performed alongside Britney Spears in a memorable medley performance. They had three nominations that night as well, though they lost out in every category.

Can you believe Taylor Swift didn’t win a Moonman at her first VMAs? Yep, 2008 marked the star’s inaugural MTV Video Music Awards appearance. She was up for best new artist but lost to Tokio Hotel. 

In 2012, One Direction wowed at their first ever VMAs. They won in every category in which they were nominated, taking home three Moonmen. They also performed their hit “One Thing” that night.

Usher arrived at the 1998 MTV VMAs as a first-time attendee. He performed his song “My Way” at the pre-show and was up for best R&B video for his song “You Make Me Wanna.” 

In 2010, Nicki Minaj arrived at her first MTV VMAs in this peachy jumpsuit paired with metallic blue pumps and hot pink hair. It was one of the first times she’d appeared on the network. She performed on the pre-show with will.i.am, presented best male video with Katy Perry and was even up for best new artist. 

Selena Gomez walked her first VMAs carpet in 2010 in this slinky silver number by Reem Acra. 

“American Idol” winner Kelly Clarkson was on hand for the VMAs for the first time in 2002. The singer rocked jeans, a white blouse and a lengthy necklace for the occasion, where she presented best new artist alongside “Idol” runner-up Justin Guarini and the show’s judges, Simon Cowell, Paula Abdul and Randy Jackson. 

The Jonas Brothers walked their first MTV Video Music Awards red carpet in 2008 in complementary suits. They performed their hit song “Lovebug” during the show, where they were nominated for two Moonmen.

Eminem was a winner at his first MTV VMAs! He picked up the Moonman for best new artist in 1999 thanks to the success of his song “My Name Is.” 

Katy Perry attended her first VMAs back in 2008. That year, she was up for best new artist — though she lost to Tokio Hotel. The video for her debut song, “I Kissed A Girl,” also picked up four nominations. 

JAY-Z arrived at his first VMAs in 1999. He won best rap video for “Can I Get A…,” which he performed in a medley of his tunes during the show.

Miley Cyrus attended her first VMAs in 2008 as a best new artist nominee. She was up for her song “7 Things” alongside stars like Katy Perry and Taylor Swift, but they all lost out to Tokio Hotel.

2013 marked the ladies of Fifth Harmony’s first time at the big show. Camila Cabello, Ally Brooke, Normani Kordei, Dinah Jane and Lauren Jauregui walked the VMAs red carpet together for the first time that night.

Shawn Mendes stepped onto his first VMAs red carpet in 2015. He looked sharp in a leather jacket, gray T-shirt, black jeans and boots. 

The 2008 MTV VMAs marked Demi Lovato’s first time at the show. She rocked this Herve Leger bandage dress, which was all the rage that year.

Bruno Mars looked sharp at his first ever VMAs back in 2010. That year, he was up for one Moonman for his work on B.o.B’s song “Nothin’ on You,” which helped him make it big.