Miley Cyrus – 22 Controversies and Crazy Moments

Remember that shocking Robin Thicke performance? Yeah, we also wish we could erase it from our memories.
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miley cyrus crazy moments

Content warning: This article contains mature themes.

“I know I used to be crazy / I know I used to be fun / You say I used to be wild / I say I used to be young.”

-You can say that again, Miley!

She’s over her “crazy phase,” and is now grown-up, collaborating with Beyoncé and well, buying herself flowers. But if there’s one fact about Miley Cyrus, it’s that she’s not shy of giving us the odd controversy.

Miley circa 2008-2015 was the scandalous ‘it-girl’ who broke headlines, turning her PG princess image into a twerking teenage rebel.

Although she’s no longer partying in the USA, this controversial celeb has a history of shocking us, from the moment she broke free from the Disney scene.

Having gone full circle with her teenage trials in the public eye, we’re diving into the past to dig out Miley Cyrus’ controversies and most crazy moments.

1. Miley Poses for Vanity Fair

Miley’s controversial past starts right here, in this absolutely gob-smacking moment, that we, quite frankly would rather delete from our memories.

At just 15-years-old, Miley poses for Vanity Fair, wearing nothing but a sheet. Being shirtless and showing her bare back, the Disney icon receives backlash for the scandalous shoot, forcing her to apologize, and making the magazine take down the image from its site. 

2. Miley Cyber Bullies Selena Gomez, Demi Lovato

Miley vs. Demi and Selena in 2008 – what a time to be alive.

Being a typical, naughty teen, Miley is caught mocking her Disney rivals, Demi Lovato and Selena Gomez in a “parody” video.

Alongside her BFF Mandy Jiroux, the Plastic Hearts singer is seen mimicking the stars and making fun of one of their videos.

Although the girls would later deny doing this with cruel intentions, they took the video down and apologized for their actions.

3. Miley is a Victim of the MySpace Hack

She may have been a not-so-innocent teen, but at the young age of 15, Miley fell prey to hackers.

Her MySpace account gets cracked into, leaking provocative photos of her posing for her then-boyfriend, Thomas Sturges. The hacker is later sentenced, but these photos still tarnish Miley’s squeaky-clean Disney persona.

miley cyrus dressed funny as a teenager
mileycyrus | Instagram

4. Miley Pole Dances at the Teen Choice Awards

While the pop princess transitions out of her Hannah Montana phase, she gives fans a little insight of what’s in store by dancing on a pole at her Party in the USA performance at the 2009 Teen Choice Awards.

That this was just the start of more wild controversies to come…

5. Miley Lap Dances for Her Producer

We know they say you should have good relations with your colleagues – but we’re pretty sure this is bordering on inappropriate…

In the summer of 2010, young Miley is captured “dirty dancing” on her producer in secret footage obtained by TMZ. The weird video which was soon removed, left many fans confused and a little sickened to say the least.

6. Miley’s Caught Bong Smoking

In shocking footage leaked in 2010, the teenage rebel is caught smoking a hallucinogenic herb, and heard asking for “more of that sh*t.”

Miley later realized what a bad example she was setting for her young fans and so apologized, saying she “isn’t perfect.”

7. Miley Cuts Her Long Hair

Miley’s signature sweet look takes a new hot turn, introducing a brand new chapter in her life. To bid good riddance to her pristine Disney image, the singer cuts off her luscious locks.

The daring star sports her iconic peroxide pixie cut and states that she’s “never felt more me.”

Despite many criticizing the look, (they really called her Draco Malfoy) Miley admits the transformation was to raise money for cancer.

miley cyrus cuts her hair short
mileycyrus | Instagram

8. Miley Performs at the 2013 VMAs

It’s 2013, and all is calm in the pop culture world – until this particular tongue-wagging star hits the stage at the MTV Video Music Awards.

Miley strips down into a latex two-piece and uses a foam finger to create provocative gestures, whilst twerking on 36 year-old singer, Robin Thicke.

While it isn’t Miley’s finest moment, this staple performance in music history is the first of many scandals to come…

9. Miley’s NSFW Terry Richardson Photoshoot

Fashion photographer, Terry Richardson, releases a series of provocative images for Candy magazine, sending shock-waves throughout the entire globe.

Miley leaves little to the imagination and even pushes the boundaries by wearing a strap-on. It’s no surprise that some begin naming her the worst role model ever.

miley cyrus posing scandalously
mileycyrus | Instagram

10. Miley’s ‘Wrecking Ball’ Video Breaks the Internet

If you thought Miley Cyrus’ controversies peaked at the VMAs, you’re wrong.

The girl-gone-wild steals headlines once more when she releases her music video for Wrecking Ball.

From swinging bare on a wrecking ball to licking a sledgehammer, this clip takes the singer’s provocativeness to a whole new level.

11. Miley Smokes on Stage

Come 2013, and it’s clear Miley’s innocent Disney persona is gone.

We all know the popular star isn’t shy of sharing her love for marijuana. But she takes her admiration to extremes when she lights, what appears to be a joint, on stage at the MTV EMA Awards.

12. Miley Calls her Dad Out for Cheating

Miley gives her family feud a global audience by threatening to leak their dirty laundry to her millions of followers.

Obviously, the ballsy star is just bluffing, as we’re still unaware of what issues actually went down in the Cyrus household at that time.

miley cyrus tweets about her dad cheating

13. Miley Kisses Katy Perry

In case you ever wanted to know this piece of important trivia, Miley and Katy locked lips during her Bangerz tour in 2014. And well, apparently it wasn’t the only time the pair shared a friendly kiss.

The pop icons have been friends since their teens, and it’s even speculated that Perry’s hit single, I Kissed a Girl was actually inspired by her close relationship with Miley.

katy perry and miley cyrus kiss
mileycyrus | Instagram

14. Miley Locks Lips with Alexander Wang

Surprisingly (or not), Miley makes headlines once again.

This time, her shocking outfit at Fashion Week raises eyebrows (which includes bright shades, lingerie pasties and NOTHING ELSE), and her make-out sesh with man of the hour, Alexander Wang gags everyone.

15. Miley Takes a Homeless Convict to the VMAs

Miley showcases her philanthropic side when she attends the 2014 MTV VMAs with a homeless man. The star accepts her award with Jesse Helt by her side, in efforts to make a plea for homeless youth in America

Helt, 22 at the time, met Miley at a nonprofit group that aims to help kids finds homes. But information comes to light that this guy actually has a criminal record and a warrant for his arrest.

At least she tried to do something good?

miley cyrus with a homeless man she took to the vmas
mileycyrus | Instagram

16. Miley Supports the “Free the Nipple Campaign”

She might be a wild one, but at least she fights for what she believes in.

The “Free the Nipple” campaign that advocates for gender equality goes viral in 2014. And guess who’s quick to jump on the bandwagon?

Miley drops jaws by taking to Instagram and sharing a selection of NSFW photos for the world to see.

miley cyrus wearing a crazy pink wig
mileycyrus | Instagram

17. Miley Uses Indecent Props on Stage

Miley makes sure her tour goes down in history by wearing prosthetic breasts and a strap-on during her Dead Petz tour.

From wearing provocative outfits to lighting up on stage, these controversial performances officially wipe out Miley’s squeaky-clean Hannah Montana phase.

miley cyrus in her don't call me angel video
mileycyrus | Instagram

18. Miley Strips Down for V Magazine

After a series of controversial performances and shoots, it was only a matter of time before this scandalous star done another shocking photoshoot.

The daring superstar bares it all for her behind-the-scenes photoshoot with V Magazine. Miley is captured posing in the buff for the magazine’s controversial ‘Diary of a Dirty Hippie’ edition in 2015, leaving many fans stunned.

19. Miley Fights With Nicki Minaj

The free-spirited popstar makes jabs at rap queen, Nicki Minaj by calling her “not nice” after her public feud with Taylor Swift. So what does the rapper do?

In what is one of Nicki Minaj’s most famous feuds, she calls Miley out on stage at the 2015 MTV VMA Awards saying, “back to this b*tch that had a lot to say about me in the press. Miley, what’s good?”

That must have stung like a bee! And it still goes down as one of the most epic celebrity feuds of all time!

20. Miley Pees in Public

Most celebs are papped getting drunk or tripping over. But, on her 23rd birthday, Miley is caught peeing in public.

Let’s just say there’s nothing that can humiliate this star…

21. Miley Is Accused of Cheating on Liam Hemsworth

Power couple, Miley and Liam Hemsworth shocked the nation when they married in December 2018, but struck the world dumb when they announced their divorce just eight months later.

Their split soon causes an even bigger media frenzy when Miley is spotted kissing Kaitlynn Carter, one day after her she announces her split from Liam.

But Miley made sure to address any cheating rumors, by tweeting, “I can admit to a lot of things but I refuse to admit that my marriage ended because of cheating.”

miley cyrus with Kaitlynn Carter
kaitlynn | Instagram

22. Miley Rants about Slut-Shaming

After much gossip and scandal about Miley’s relationships, the superstar sets the record straight with a lengthy post on social media.

Feeling “slut-shamed” for dating, the singer goes in during her outrage, which we must admit, has some truth in it. Miley rants about how the media treats her relationships, claiming that famous men aren’t treated the same when they date multiple women.

miley cyrus rants on twitter about slut-shaming
mileycyrus | Twitter

Has Miley Cyrus been problematic and excessive? Absolutely. But, who didn’t do a lot of stupid stuff in their late teens, early 20s?

Perhaps growing up in the spotlight took a toll on this scandalous celeb, but despite Miley’s crazy moments, she still remains supremely talented.

Now that she’s shaken off her bad girl persona, we’re witnessing her talent even more. Just watch her Grammy Awards performance, and you’ll realize she’s a vocal beast and fabulous entertainer.

Whether you love her or hate her, Miley Cyrus has surely made a mark on the entertainment world.


Tale Tellers

  • Joanna Zambas

    Joanna has a history in the fashion world; having studied lifestyle and fashion journalism at BA and MA level, she then proceeded to work in the hustle and bustle of fashion PR. These days you can find her working in the marketing sphere, content writing and religiously following the ins and outs of the entertainment world. She’s obsessed with celebrity style and the Kardashians – but who isn’t?!

  • Angela Stephanou

    After completing her BA in Communication, Media and Film studies, Angela launched Tell Tales Online, and now writes and oversees the content and strategy across the site. As a pop culture junkie, she follows more celebs than real-life people, her guilty pleasure is watching The Kardashians, but she's also a fan of Marvel and Game of Thrones.

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