Miley Cyrus's Best MTV VMAs Moments

2008: Taylor Swift Interviewed Miley Cyrus and Katy Perry

Image Source: Getty / Kevin Mazur

On behalf of MTV, Taylor interviewed both Miley and Katy. All three were nominated for best new artist.

1 / 32

2008: Miley Cyrus Was Nominated For Best New Artist

Image Source: Getty / Kevin Mazur

Miley attended the show with her mom, Tish, that year, although she lost out on the award to Tokio Hotel.

2 / 32

2008: Miley Cyrus Lost Best New Artist to Tokio Hotel

Image Source: Getty / Kevin Mazur

Although Miley lost out to Tokio Hotel for best new artist, she posed for a picture with the group backstage.

3 / 32

2011: Miley Cyrus Debuted a More Grown-Up Look

Image Source: Getty / Gregg DeGuire

The singer arrived to the VMAs wearing Roberto Cavalli, and the dress earned her a place on Rolling Stone's best-dressed list.

4 / 32

2011: Miley Cyrus and Shaun White Presented Best Rock Video

Image Source: Getty / Jeff Kravitz

Miley wasn't nominated for any awards that evening. Instead, she and Shaun presented the best rock video award to Foo Fighters for "Walk."

5 / 32

2012: Miley Cyrus Debuted a New Look With Her Platinum Pixie Cut

Image Source: Getty / Frederick M. Brown

She attended the show with her sister, Brandi Cyrus. Like in 2011, she wasn't nominated.

6 / 32

2012: Miley Cyrus and Mac Miller Introduced Pink's Performance

Image Source: Getty / Lester Cohen

The pair introduced Pink's mashup performance of "Get the Party Started" and "Blow Me (One Last Kiss)."

7 / 32

2013: Miley Cyrus Posed on the Red Carpet With Mike Will Made It

Image Source: Getty / Dimitrios Kambouris

Mike Will Made It is the producer of Miley's song "We Can't Stop," which was nominated for best female video, best pop video, best editing, and song of the summer that year.

8 / 32

2013: Miley Cyrus Performed "We Can't Stop"

Image Source: Getty / Jeff Kravitz

Now known as the "twerk heard round the world," Miley's performance of "We Can't Stop" was seen as a departure from her Disney days. She performed in a bear-themed one-piece surrounded by some trippy teddy bears.

9 / 32

2013: Miley Cyrus Joined Robin Thicke on Stage For "Blurred Lines"

After her performance of "We Can't Stop," she stripped down to a latex two-piece and twerked on Robin Thicke as he performed "Blurred Lines." She later told MTV that she "doesn't pay attention to the negative" and both she and Robin knew they were going to make history with the performance.

10 / 32

2014: Miley Cyrus Posed on the Red Carpet With Snoop Dogg

Image Source: Getty / Christopher Polk

Miley stopped to pose with Snoop Dogg. She was featured on his 2013 song "Ashtrays and Heartbreaks."

11 / 32

2014: Miley Cyrus Sat With Sam Smith

Image Source: Getty / MTV/MTV1415

Miley took a moment for a picture with Sam, who was nominated that evening for best male video and artist to watch for "Stay With Me." He also performed the song during the ceremony.

12 / 32

2014: Miley Cyrus Was Kissed by Ariana Grande

Image Source: Getty / Christopher Polk/MTV1415

The pair shared this absolutely adorable moment, with Miley winning video of the year and Ariana winning best pop video.

13 / 32

2014: Jesse Helt Accepted Miley Cyrus's Video of the Year Award

Image Source: Getty / MTV/MTV1415

Miley had Jesse, who was homeless at the time, accept the award on her behalf. During his speech, he explained how people watching could donate to My Friend's Place, a homeless shelter in Los Angeles.

14 / 32

2014: Miley Cyrus Posed Backstage With Her Video of the Year Award

Image Source: Getty / PA Images

Miley won the award for "Wrecking Ball."

15 / 32

2015: Miley Cyrus Arrived in Style

Image Source: Getty / Frank Trapper

She wore a custom Versace silver harness-like top and skirt as she arrived at the 2015 awards.

16 / 32

2015: Miley Cyrus Posed With Her Family Before the Show

Image Source: Getty / Larry Busacca

Miley couldn't pass up a moment with her family, posing with Tish Cyrus, Braison Cyrus, Noah Cyrus, Billy Ray Cyrus, and Brandi Cyrus.

17 / 32

2015: Miley Cyrus Started the Show Off in Sequins

Image Source: Getty / Michael Tran

She wore a jumpsuit by The Blonds.

18 / 32

2015: Miley Cyrus Reacted to Nicki Minaj's Call-Out

Image Source: Getty / Kevin Mazur/MTV1415

After Nicki won best hip-hop video, she turned to Miley and said, "Back to this b*tch that had a lot to say about me the other day in the press. Miley, what's good?" To which Miley responded, "Nicki, congratu-f*cking-lations."

19 / 32

2015: Miley Cyrus Was Essentially a Walking Rainbow

Image Source: Getty / Lester Cohen

She dared to be square in a piece by Ágatha Ruiz de la Prada.

20 / 32

2015: Miley Cyrus Was Totally Tinselfied

Image Source: Getty / Michael Tran

At one point during the show, Miley described the VMAs red carpet as "Christmas in August," so it was only fitting she wore a custom Prada tinsel jacket.

21 / 32

2015: Miley Cyrus Took Futuristic to a New Level

Image Source: Getty / Michael Tran

Miley's Fifth Element-esque vinyl dress was by Mamadoux.

22 / 32

2015: Miley Cyrus's Daring Dotted Dress Stole the Spotlight

Image Source: Getty / Michael Tran

Much like her red carpet look, Miley's dotted ensemble was custom Versace.

23 / 32

2015: Miley Cyrus Was Pretty in Pink

Image Source: Getty / Michael Tran

Miley showed her love for Versace during her hosting gig, wearing a pink bra and metallic pink tuxedo pants from the brand.

24 / 32

2015: Miley Cyrus Came in Like a Disco Ball

Image Source: Getty / Michael Tran

Switching things up from Versace, Miley changed into a full-mirror look designed by Prada.

25 / 32

2015: Miley Performed "Dooo It!"

Image Source: Getty / Michael Tran

Miley's performance was introduced by members of the Happy Hippie Foundation, a nonprofit organization founded by Miley that fights injustice facing homeless youth, LGBTQ+ youth, and other vulnerable populations. During her performance, she was supported by famous drag performers wearing custom BCalla.

26 / 32

2015: Miley Posed Backstage With Drag Performers

Image Source: Getty / Jeff Kravitz/MTV1415

Miley's "Dooo It!" performance wouldn't have been complete without backup from Alexis Mateo, Alyssa Edwards, Amazon Ashley, Barbie's Addiction, Cake Moss, Carmen Carrera, Courtney Act, Cupcake Canne, Delta Work, Gia Gunn, Jaidynn Diore Fierce, Jasmine Masters, Jessica Wild, Jiggly Caliente, Laganja Estranja, Mariah Paris Balenciaga, Melissa Befierce, Miss Fame, Monica Beverly Hillz, Pandora Boxx, Pearl, Porkchop, Shangela, Sonique, Tammie Brown, Trinity K. Bonet, Violet Chachki, Vivacious, Vivienne Pinay, and Willam.

27 / 32