There might not be a celebrity in Hollywood that has had a more significant transition under the public eye than Miley Cyrus. You most likely fell in love with her when she was rocking out on Hannah Montana, but as you’ll learn from this list it didn’t take long for her to start rocking out with alcohol, drugs and of course, a lack of clothing. Not that you’re going to be left complaining about all the fantastic photos that we’ve compiled for you below.
We’re jumping way back to Cyrus’ first ever film role, to one of her most recent and captivating Instagram posts that help explain why she’s one of the most popular and talked about celebrities.
Included are details about her love life with fellow celebrity Liam Hemsworth, her musical and acting successes (and failures), her biggest controversies – which are also often her most scandalous moments – and all the various life experiences that helped turn Miley into the person she is today.
Included are also quotes from Miley and her father who helps explain why he doesn’t mind the world looking at his daughter without clothes on and what Miley’s aspirations are when it comes to marijuana and yoga.
There isn’t a Miley Cyrus fan out there who won’t enjoy going through this list, so feel encouraged to comment and share the list on social media!
16. Her First Two Film Roles
Miley Cyrus growing up in the spotlight is perhaps no more evident than the fact that we open up the list with an incredibly young Cyrus in the television drama Doc (where her father was a lead) and the Tim Burton directed Big Fish when she was 11 years old. As a fun fact, she is listed in the credits for Big Fish as Destiny Cyrus, which is her actual first name.
Cyrus had her name legally changed to Miley when she was 18 and has said in past interviews that she had been nicknamed Miley when she was a baby and her father Billy Ray Cyrus noticed how she was always smiling.
15. Her Days On Hannah Montana
When Miley Cyrus was starting out on Hannah Montana, she had a father that was well aware that show business can be a brutal business. Miley opened up in a past interview about what some of his fears were,
“He wasn’t worried about me going crazy – my dad isn’t like that, and my parents trust us and know us. It was more about the heartbreak of work. There’s a lot of stress, and the company is putting all those millions, depending on a child.”
He wasn’t worried about you going crazy Miley? Let’s just save Billy Ray some years of therapy and tell him now that he definitely doesn’t want to get to the end of this list where her wild and “crazy” side is absolutely going to get exposed including wearing pasties on Jimmy Kimmel, pole dancing and twerking all up on Santa.
14. Her First Tour (2007)
When Miley Cyrus was making the transition from Hannah Montana into Miley Cyrus in the public eye, one of the main ways she did this was by releasing her 2nd album entitled Hannah Montana 2: Meet Miley Cyrus which was half the soundtrack of the newest season of Hannah Montana, and half Miley being Miley.
Cyrus used this opportunity to also tour for the first time, including representing “both personalities” over the course of her concert.
It ended up being a huge success, earning over $50 million and when the concert DVD was released it also made over $70 million.
13. Pole Dances At 2009 Teen Choice Awards
Miley Cyrus knew that all eyes were going to be on her when she took to the stage at the 2009 Teen Choice Awards and elected to start swinging around on the pole with some very short shorts. Cyrus was 16 years old at the time but had plenty of reason to celebrate, taking home 6 awards at that year’s show.
While some critics bashed Miley for embracing her raunchier side (ha, if only they knew what the future held), her father was vocal in his support,
“You know what? I just think that Miley loves entertaining people. She loves singing and songwriting. I always tell her to love what you’re doing and stay focused for the love of the art and not worry so much about opinion. I give my kids a lot of freedom to make the art they want to make and make it in their own voice. I think it’s important.”
12. The Last Song Bombs But Lets Her Meet Liam (2010)
The Last Song remains the biggest chance that Miley Cyrus had at making a name for herself as a strong leading actress. The movie was based on a Nicholas Sparks novel and while Sparks found gold with The Notebook, that was not the case as critics panned the movie; earning it a 20% rating on RottenTomatoes with the general consensus being, “As shamelessly manipulative as any Nicholas Sparks production, The Last Song is done no favors by its miscast and overmatched star, Miley Cyrus.”
If the movie does have a positive, it is what led Cyrus to meet her now-fiancé Liam Hemsworth, so at least you know their love connection in the film was genuine. Too bad it didn’t translate to a better connection with critics and fans. As a fun twist, it’s heavily reported that Ryan Gosling and Rachel McAdams who starred in the much more successful Sparks’ movie adaptation The Notebook hated working with each other.
11. Oscars Event – Red Carpet Debut With Liam (2010)
After meeting on the set of The Last Song, Cyrus and Hemsworth quickly became an item and made their “Hollywood debut” with the above photo that was taken at an Oscars event back in 2010. The two left little doubt as they also walked The Last Song premiere as a couple.
That same year Cyrus also spoke out to MTV News about her album “Can’t Be Tamed” and admitted that Hemsworth was a large source of inspiration for much of the album, “There are a lot of songs that are about Liam. All of them are about him in a way, but it’s also about past relationships that you gotta get over and move on and just about freeing yourself from anything that you feel holds you back.”
10. The Fake Engagement + Real One (2012)
We could spend a large portion of our time on Hemsworth and Cyrus’ back and forth relationship as they dated on and off from 2010-2011, so we’re just going to save you some time and jump ahead to 2012 with the non-real engagement, which was promptly followed by an engagement.
This photo was taken at The Hunger Games premiere in March and after speculation grew over the ring on “that finger”, Miley went to Twitter to say “I’m not engaged. I’ve worn this same ring on this finger since November! People just wanna find something to talk about! It’s a topaz people!”
Yet maybe people talking about it gave Liam some ideas because in June Liam did propose, leading Miley to say “I’m so happy to be engaged and look forward to a life of happiness with Liam.”
9. Controversial 2013 MTV VMA Performance With Robin Thicke
You know how you break up with someone and you want to do your best to not think about them? Liam definitely had a hard time with that as the last time they were photographed together in public (prior to re-hooking up later) was in 2013 and only weeks before Miley took to the stage in the above outfit.
As you’ve learned from this list, Miley Cyrus is no stranger to causing an uproar with the outfits she chooses to wear (or perhaps more fittingly not wear) on stage and her raunchy behavior. So naturally back in 2013 when she took to the stage alongside Robin Thicke, all eyes were glued to the TV.
They then got to see Miley strip down to the above outfit you see and twerk all over Thicke in a performance that one critic said resembled a bad acid trip.
It ended up being a huge positive for Cyrus’ career, however, as it was reported that it led to a flurry of social media activity (including 213,000 new Twitter followers) and was monumental in helping her single “Wrecking Ball” becoming the success it was, especially because it was released the same night.
8. Twerks With Santa (2013)
Ho Ho Ho, we’re sure the Santa in the above photo was definitely having himself a Merry Christmas after Miley Cyrus decided to take to the stage and twerk all over his junk. Cyrus elected to bring out her naughty side when she performed a Jingle Bell Ball Performance back in 2013. In fact, the man playing Santa is her assistant!
“I’m making him get on stage tonight because he’s not a very good assistant, but he’s a hell of a bad Santa. So that’s his new gig. He’s a little bit of an alcoholic, so he’ll get on stage, get drunk and just stumble around,” said Cyrus when talking about the performance.
7. MTV 2014 Video Of The Year
How fitting is it that one year after Miley Cyrus was stirring up controversy for stripping down on stage at the 2013 MTV Music Awards, that she would be back on that stage a year later and accepting an award for her song “Wrecking Ball” which won Video of the Year.
Perhaps in classic Miley Cyrus fashion, the music video also features Miley Cyrus strip down to her birthday suit; including swinging on a wrecking ball.
The video was viewed close to 20 million times in its first 24 hours, helping capture all the attention that was on Cyrus following her performance at the 2013 show.
When talking about the video, Cyrus said,
6. Showing Her Love Of Pasties On Jimmy Kimmel (2015)
Miley Cyrus is no stranger to stripping down to her birthday suit, but when she was asked to appear on the Jimmy Kimmel show back in 2015 she knew she had to dress at least slightly more appropriately. So perhaps that’s why she went for an outfit that featured her wearing only heart shaped pasties over her breasts.
Kimmel, perhaps understandably admitted during the interview that her outfit was making him blush but Cyrus had an easy solution on if she catches people looking,
“You could just be like ‘stop staring at my tits’ and then the convo keeps going.”
Cyrus, a supporter of the”Free the Nipple” movement also has the support of her father to keep baring it all
“He would rather me have my tits out and be a good person than having a shirt on and be a bitch. I’m showing my boobs and no one had a problem, but the nipples are covered so somehow that’s okay. America is actually fine with tits. It’s nipples they don’t like.”
5. Milky Milky Milk Tour Fake Body Parts (2015)
When you attend a Miley Cyrus concert, you can expect things to get pretty extreme. As was the case with her 2015 concert tour entitled Milky Milky Milk Tour which ran in only 8 cities and for one month but was able to bring in over $4.5 million in revenue.
Among the many eye-catching outfits that Cyrus would wear, one that garnered the most attention was one styled in S&M and featured Cyrus wearing fake breasts and rocking a prosthetic penis.
Cyrus, known for her fan interaction, also had no issue with fans shoving dollar bills in her mouth in between songs. Sounds like a pretty great way to get sick if you ask us, but when it comes to questioning Miley’s actions that is far from the craziest thing she’s done.
4. Shows Off Her Yoga Skills (April 2016)
You don’t have to look at Miley Cyrus’ Instagram page for long before it becomes very clear that Cyrus loves showing off her flexibility in a variety of yoga poses. The one above was posted back in April 2016 and featured the humorous caption “fri-namaste”.
Cyrus has also been open about her love of marijuana, leading some reports to say that she may be looking to combine her two loves
“Miley thinks it’s something that could legitimately catch on, especially with her name attached to it. Her motto is basically, bust your ass for an hour in yoga and then wind down with some [marijuana].”
3. Appears In Crisis In Six Scenes (September 2016)
Miley Cyrus may be plenty comfortable in a recording studio, but in 2016 she got to spend a large portion of her time hanging out with Woody Allen as she (alongside Woody) starred in his latest venture; a television program entitled Crisis in Six Scenes.
When talking about her appeal of working with Woody, Cyrus mentioned his dedication to not working too late,
“I loved working with Woody. You do like two takes. He just wants to go home and have dinner with his wife. One night it was 5:30, and the camera operator wanted to do another take. He goes, ‘I can’t dedicate my entire life to making movies.'”
2. Confirms Engagement To Liam Hemsworth (October 27th, 2016)
You’re not going to be able to complete the transition that Liam Hemsworth and Miley Cyrus went through without including the moment when she finally confirmed her engagement.
Taking to the Ellen show back in October, Miley confirmed that the two were in fact engaged again after rekindling things at the start of 2016; even if she wasn’t the biggest fan of the ring.
“This is really weird because this is like real jewelry and most of my jewelry is made out of gummy bears and cotton candy … they don’t look that good together because they kind of mix up. So sometimes I replace it with an actual unicorn or a Looney Tune. And [Hemsworth’s] kind of like, ‘What’s going on?’ I am like, ‘This isn’t really my aesthetic, but I’ll wear it because you love me.’”
1. Looking Good On Instagram In 2017
When you consider Miley Cyrus has over 65 million followers on Instagram, perhaps you’re not too shocked that one of our last photos is one of her most popular photos from 2017.
Needless to say, anything that she posts online gets plenty of traffic, which may be why she also admitted that she’s tried to move away from using Instagram herself,
“I don’t have Instagram on my phone anymore. This chick at the office, I gave her my password. I’ll send her a picture of me feeding the pig in a bikini: ‘Can you post, like, ‘Fuck yeah, pigs!’? Or, ‘High in a bikini!” I just don’t want to scroll. I don’t want to know what people are doing….I used to literally post four times on the hour obnoxiously, but that was in a heavy art phase.”
While she may not be blowing up on Instagram as much as her fans would hope, perhaps we’ll see some bikini pictures as the summer months roll in!