Miley Cyrus' wildest moments, from nearly nude Vanity Fair portrait to twerking with Robin Thicke

Miley Cyrus has been known to raise eyebrows with her risqué outfit choices and her bold dance moves.

The 26-year-old pop star — the daughter of famous singer-songwriter Billy Ray Cyrus — has been making headlines since she was a teenager. In recent years, Cyrus has shattered her wholesome Disney Channel child star image and opted to forge her own path.

She has been open about her previous use of marijuana and alcohol and has discussed her special relationship with Liam Hemsworth.


Here's a look back at some of Cyrus' wildest moments.

Nude Instagram post

In a March Instagram post, Cyrus posed completely nude while lounging on a beach chair — the desert behind her — in a floppy yellow hat.

"Festival season is here , I’m queer , and ready to party! 🌈🌈🌈 lets go summer 2019!" Cyrus captioned the sultry post.

"SNL" nip slip risk

Cyrus' daring outfit choice during her performance of "Nothing Breaks Like a Heart" on "Saturday Night Live" with Mark Ronson in December turned heads. The singer was nearly topless — wearing an open silver jacket that exposed her chest.

Fans watched as the star swayed during the song, questioning how the jacket managed to stay in place.


"Glue? Duct tape? What is happening?" one Twitter user asked.

"Me watching Miley Cyrus waiting for a wardrobe malfunction," another joked.

"NBC censors watching that #SNL Miley Cyrus performance be like..." one fan wrote, posting a GIF from "The Office."

VMA twerking session

Cyrus says her 2013 MTV Video Music Awards performance with Robin Thicke changed her life "forever."

"Not only was culture changed, but my life and career were changed forever," Cyrus said in a March interview with Wonderland magazine, per Entertainment Tonight. "It inspired me to use my platform for something much bigger."

During the award show, Cyrus stripped into a nude bikini on stage, stuck her tongue out and twerked on Thicke as he sang "Blurred Lines." She also held a foam finger, making suggestive movements with it throughout the performance.

“Robin is pi-ssed,” an inside source told Fox News at the time. “She was all over him, much more so than anything that was rehearsed.”

The performance sparked mixed reactions online, with some complaining about Cyrus' "disgusting" sexual gestures.

"They're overthinking it," Cyrus told the Hollywood Reporter in response to the negative feedback. "You're thinking about it more than I thought about it when I did it. I didn't even think about it, 'cause that's just me."

Mocking Lewinsky scandal

Cyrus shocked a crowd in Canada in 2014 when she brought a Bill Clinton impersonator on stage and dropped to her knees in an attempt to mock the former president's scandal with then White House intern Monica Lewinsky.

The singer simulated oral sex on the impersonator in front of fans during her debut concert for her "Bangerz" tour in February 2014, according to TMZ.

“Even though parents probably won’t think this, I think my show is educational for kids," Cyrus told HuffPost about the performance. “They’re going to be exposed to art most people don’t know about."

"Wrecking Ball" music video

Cyrus certainly "came in like a wrecking ball" in the music video for her hit song in 2013. The artist bared all, wearing nothing but brown boots in a portion of the video.

"I think the video is much more [than that]. If people get past the point I make, and you actually look at me, you can tell I look more broken than even the song sounds," Cyrus told Elvis Duran and the Morning Show after the video was released, according to E! News.

At the time, Cyrus described the video as portraying a "vulnerable" part of herself.

"For me, anything I do becomes such a big deal. I'm just having fun. Whatever people label it as it doesn't really matter. I always want to switch it up," she added.


Years later, Cyrus appeared to change her tune.

"That's something you can't take away. Swinging naked on a wrecking ball lives forever," she said on Westwood One’s "Zach Sang Show in May 2017. "Once you do that in the amass that I did, it's forever. I'm never living that down."

"I'm always the naked girl on the wrecking ball," she added. "I should have thought about how long that was going to have to follow me around."

2008 Vanity Fair shoot

Cyrus was criticized for posing in a racy portrait for renowned celebrity photographer Annie Leibovitz which was featured in Vanity Fair in 2008 when she was just a teenager.

Following backlash for the near-nude picture, which showed the then 15-year-old Disney Channel star wrapped in a satin bedsheet, Cyrus issued an apology to fans.

"I took part in a photo shoot that was supposed to be 'artistic' and now, seeing the photographs and reading the story, I feel so embarrassed," Cyrus said in a statement. "I never intended for any of this to happen and I apologize to my fans who I care so deeply about."

The backlash even prompted Leibovitz to clarify artistic decisions she made during the shoot.


"I'm sorry that my portrait of Miley has been misinterpreted," Leibovitz said in a statement at the time. "Miley and I looked at fashion photographs together and we discussed the picture in that context before we shot it. The photograph is a simple, classic portrait, shot with very little makeup, and I think it is very beautiful."

However, a decade later, Cyrus took back her apology for the Vanity Fair portrait in a profanity-laced tweet.

(Warning: this post contains crude language)

The Associated Press contributed to this report.