Stars at their very first MTV Video Music Awards – Wonderwall

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It’s one of the most entertaining shows of the year — the wild and unpredictable MTV Video Music Awards!

In honor of the 2023 MTV VMAs on Sept. 12, 2023, Wonderwall.com is bringing you photos of big stars attending the VMAs for the very first time. Let’s start with this singer…

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” during the pre-show that year.

Keep reading to see more stars at their very first MTV VMAs…

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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.” 

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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.

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Music star Alicia Keys was just 20 when she attended her first MTV Video Music Awards in 2001. That evening, she took home the Moonman for best new artist in a video for “Fallin’.”

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Avril Lavigne showed off her surprised face when she took home the Moonman for best new artist in a video for “Complicated” at the 2002 MTV Video Music Awards — which also happened to be the first one she attended! She donned her then-signature outfit: a white tank, baggy cargo pants, a ton of studded wristbands and a loose-fitting tie around her neck.

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Former Disney teen queen Hilary Duff made her MTV Video Music Awards debut in 2003. While she wasn’t nominated that year, she earned a best pop video nod in 2004 for “Come Clean.”

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

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

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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 singer rocked a crop top, white jeans and heels at her first VMAs outing, where she also performed her first hit, “Pon de Replay,” during the preshow. 

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Pop singer and “Newlyweds” star Jessica Simpson walked her first MTV Video Music Awards red carpet in 2001.

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In 2004, Ashlee Simpson made her MTV Video Music Awards debut in a chic strapless Jennifer Nicholson dress. She earned her first VMA nod the following year for best pop video for “Pieces of Me.”

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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.

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

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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.

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Beyonce attended her very first MTV VMAs more than 20 years ago in 2000! Yep, the superstar attended as a member of Destiny’s Child with fellow singers Kelly Rowland and Michelle Williams — then took home a Moonman for best R&B video for “Say My Name.” 

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Nelly Furtado showed up to her first MTV Video Music Awards ceremony in 2001 in an all-blue ensemble. The Canadian singer-songwriter had to wait five more years before earning her first three MTV VMA nominations: best pop video, best female video and best dance video for “Promiscuous Girl.”

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In 2009, Lady Gaga attended her very first MTV 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.

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

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Can you believe Taylor Swift didn’t win a Moonman at her first MTV VMAs, which was in 2008? She was up for best new artist but lost to German rockers Tokio Hotel. (Fun fact: Heidi Klum’s third husband, Tom Kaulitz, is in that band!)

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

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When did R&B singer JoJo make her MTV Video Music Awards debut? In 2004, the same year she made history as the youngest best new artist nominee!

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

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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 preshow with will.i.am, presented best male video with Katy Perry and was even up for best new artist. 

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

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“American Idol” winner Kelly Clarkson was on hand for the MTV 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. 

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Jesse McCartney and Katie Cassidy were dating when they attended the 2005 MTV VMAs in Miami in 2005 when he was up for best pop video for “Beautiful Soul.” It was his first time there, but Katie had previously attended in 2002.

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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.

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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.” 

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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.

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Miley Cyrus attended her first MTV 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.

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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 that night.

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Olivia Rodrigo graced the MTV Video Music Awards red carpet with her presence for the first time in 2021! In addition to turning heads in her gorgeous corseted Jean Paul Gaultier dress, she took home three Moonmen that night for best new artist, song of the year and push performance of the year for “drivers license.”

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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. 

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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. 

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Look at that hair! Pink‘s MTV Video Music Awards debut in 2000 was one of the show’s most memorable! That year, she was nominated for best new artist in a video for “There You Go.”