Popsugar Celebrity Award Season Miley Cyrus's Best MTV VMAs Moments From Twerkgate to Her Unique Style Choices: Miley Cyrus Knows What's Good at the VMAs 18 August 2020 by Grayson Gilcrease Image Source: Getty / Jeff Kravitz Some of the most interesting VMA moments over the years have included Miley Cyrus, and here's hoping 2020 won't be any different. Although her twerked-out rendition of "We Can't Stop" is a tough act to follow, from the looks of her "Midnight Sky" music video, it may just get topped. In preparation of her performance on Aug. 30, we thought it was time to take a look back at some of the times where she was just being Miley — or rather, her best moments at the VMAs. Related: Miley Cyrus Seemingly Makes Reference to Her Publicized Romances in "Midnight Sky" 2008: Taylor Swift Interviewed Miley Cyrus and Katy Perry Image Source: Getty / Kevin Mazur On behalf of MTV, Taylor interviewed both Miley and Katy in "fashion central." 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 lost out 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 presented best rock video along with Shaun 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 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 Onstage For "Blurred Lines" Image Source: Getty / Jeff Kravitz 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 collaborator Snoop Dogg. She was featured on his 2013 song "Ashtrays and Heartbreaks." 11 / 32 2014: Miley Cyrus Seated With Sam Smith Image Source: Getty / MTV/MTV1415 Miley took a moment for a picture with Sam Smith, who was nominated that evening for best male video and artist to watch for "Stay With Me." He also performed the song during the 2014 VMAs. 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, which is 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 video of the year 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 and posed 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 Callout Image Source: Getty / Kevin Mazur/MTV1415 After Nicki won best hiphop 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 Agatha 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 Elemente-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 Versace Medusa pink bra and metallic pink tuxedo pants. 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 performance was introduced by members of the Happy Hippie Foundation, which is a nonprofit organisation 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 Balienciaga; 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 2015: Miley Cyrus Posed Backstage With a Moonman Image Source: Getty / picture alliance The 2015 award was designed by Jeremy Scott and would be renamed to "Moon Person" in 2017. The singer hosted the 2015 awards and wasn't nominated. 28 / 32 2017: Miley Cyrus Performed "Younger Now" Image Source: Getty / Randy Shropshire/MTV1617 Although nominated for "Malibu," Miley performed "Younger Now" alongside older couples reliving their younger days in a nod to her music video. 29 / 32 2017: Miley Cyrus Was a Rockabilly Fantasy Image Source: Getty / John Shearer During her performance of "Younger Now," Miley ditched her poodle skirt in favour of a cute pinup look. 30 / 32 2017: Miley Cyrus Posed With Millie Bobby Brown Image Source: Getty / Christopher Polk/MTV1617 Miley's look would've done Elvis Presley proud as she posed with Millie Bobby Brown after her performance of "Younger Now." 31 / 32 2019: Miley Cyrus Performed "Slide Away" Image Source: Getty / John Shearer Miley's rendition of "Slide Away" was emotional and heartfelt as the song is believed to be based on her relationship with ex-husband Liam Hemsworth. 32 / 32 Award SeasonNostalgiaMTV VMAsMusicMiley CyrusRed Carpet