Pop

With the first quarter of the 21st century coming to a close, Billboard is spending the next few months counting down our staff picks for the 25 greatest pop stars of the last 25 years. We’ve already named our Honorable Mentions and our No. 25, No. 24, No. 23, No. 22, No. 21, No. 20, No. 19, No. 18, No. 17 and No. 16 stars, and now we remember the century in Miley Cyrus — who at age 31 has already lived through several artistic lifetimes, generating numerous pop classics and countless unforgettable moments in the process.

For many artists, it’s their hit songs, pop culture-defining albums or chart successes that are easiest to pinpoint as landmarks for the most pivotal stages of their careers. But for Miley Cyrus, it’s hair. 

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Though she certainly has plenty of all the above accomplishments, the 31-year-old generational talent’s phases of life have always been irrevocably intertwined with what’s going on atop her head — from the blonde wig that made her famous in the mid 2000s to the bleached pixie cut that introduced the world to a very different Miley in 2012. It goes beyond the public’s obsession with beauty standards, which a thin, blue-eyed Cyrus would embody for the first several years of her career before rejecting that mold altogether; the singer’s hair has had a way of symbolizing where she’s at personally and artistically over the years.   

And where she’s been, in both regards, has been all over the map. From eager Disney Channel prodigy to unruly pop outlaw, freewheeling genre experimenter and mature modern hitmaker, Cyrus’ knack for earnest reinvention has sustained her through all the peaks and valleys of her career. With no shortage of chart hits and even more iconic culture-shocking moments, she’s endured as one of the century’s most significant pop stars – because no matter what style she’s trying out, at the end of the day, she’s always still just being Miley. 

Born Destiny Hope Cyrus on Nov. 23, 1992, in the Nashville metropolitan area of Tennessee, the most recognizable head of hair in the young star’s childhood wasn’t her own, but father Billy Ray’s signature mullet. Miley, who legally adopted her childhood nickname in 2008, grew up in a constellation of other stars before she would become one herself, with her dad becoming a country sensation in the ’90s for the massive crossover hit “Achy Breaky Heart” and her godmother being none other than Dolly Parton.

Seeing Billy Ray act on his early-’00s medical drama Doc inspired Miley to want to be a performer, too, leading her to audition for Disney Channel’s Hannah Montana at just 12 years old. After first reading for the part of sidekick Lily, the preteen was instead asked to try for the sitcom’s main character instead: Miley Ray Stewart, a Malibu teen who could transform at any moment to global pop sensation Hannah Montana, with a wig that somehow carried the same camouflaging powers as Clark Kent’s glasses. Billy Ray was cast as her character’s dad, their natural chemistry translating beautifully on screen.  

It’s hard to describe just how magnetic Cyrus was on that show. Here was a girl who could deliver a cheesy catch phrase — usually “Sweet niblets!” or  “Yeeee doggies!” — like a seasoned comedic actor, unafraid of appearing unattractive or goofy in service of a good bit with an innate power and resonance in her voice that was almost unnatural for her age. 

Miley Cyrus

Sam Emerson/Walt Disney Co./Courtesy Everett Collection

Miley Cyrus

Jeff Kravitz/FilmMagic

And you’d better believe that Disney capitalized on her raw talent. During Hannah Montana’s run from 2006 to 2011, the children’s network churned out four seasons of TV, five soundtrack albums, a feature film, a tour and a concert movie — not to mention countless clothing lines, lunch boxes, backpacks, accessories, makeup, blankets, throw pillows and Happy Meal toys plastered with Miley and Hannah’s shared face.  

All the while, Cyrus was essentially holding down two music careers at once, signing with Walt Disney Records for all things Hannah and then with Hollywood Records for her own work as Miley. Her first two albums, Hannah Montana and Hannah Montana 2/Meet Miley Cyrus both debuted at No. 1 on the Billboard 200. On the Best of Both Worlds Tour, she performed one half as herself and the other as her alter ego (the trek grossed more than $54 million, according to Billboard Boxscore). She scored numerous chart hits under Hannah — “Best of Both Worlds,” “Nobody’s Perfect” and 18 more tracks made the Billboard Hot 100 during the show’s run – which gave way to additional hits as Miley. Both “See You Again” and the Nick Jonas breakup anthem “7 Things” reached the Hot 100 top 10 and gave her credibility outside of the Disneyverse, leading pop fans to start taking her seriously outside of her lane as a kids’ TV star.   

As Miley and Hannah became increasingly inextricably linked, however, it got harder for the public to detangle Miley Cyrus from Hannah Montana, or even from Miley Stewart. Activities like posing bare-shouldered on the cover of Vanity Fair in 2008 or hitting a salvia bong the week of her 18th birthday in 2010 weren’t the mere antics of a maturing teenage girl, they were affronts to a squeaky-clean, million-dollar brand dependent on the adoration of little kids and the approval of their parents. This left Cyrus with few options for mapping out her career post-Hannah: risk spending the rest of her life living in her own character’s shadow or control the narrative by inelegantly demolishing that character and forcing the world to watch. We all know which route she chose – but first, attempts at a more seamless transition were made.  

In 2009, the same year Hot 100 No. 4 hit ballad “The Climb” and barn-raising dance tune “Hoedown Throwdown” came out for Hannah Montana: The Movie’s soundtrack, Cyrus dropped the 7-track EP The Time of Our Lives, featuring what is still one of her most beloved and easily recognizable hits: “Party in the U.S.A.” The Dr. Luke-produced quasi-patriotic banger immediately became Cyrus’ biggest home run so far, exploding on pop radio and reaching No. 2 on the Hot 100 thanks to its charming lyrics and infectious main hook. (Seriously, how does one not sing along to that “Yeah-ee-ah-ee-ah-ee-ah” in the chorus?) The track also offered a glimpse at what her post-Disney pop music career might’ve looked like for the next decade if she’d wanted it: polished, widely palatable and performed by the same Miley Hannah Montana fans knew and loved, just with a more mature sound and maybe slightly shorter shorts

But then, she got on stage at that year’s Teen Choice Awards and innocently performed the track on top of a prop ice cream cart, holding onto a silver bar so as not to fall off while dancers pushed her around. Except, the masses didn’t see it that way: The showcase sparked global gasps and pearl-clutching over what scandalized audiences interpreted as a risqué pole dance. One famous tabloid headline asked if Miley was “turning into Britney.” Instead of coming to her defense, her network quickly released a statement: “Disney Channel won’t be commenting on that performance, although parents can rest assured that all content presented on the Disney Channel is age-appropriate for our audience – kids 6-14 – and consistent with what our brand values are.” (This is why we can’t have nice things.) .  

After that, Miley came back with 2010’s Can’t Be Tamed, an album meant to showcase her edgier side and her last with Hollywood Records. Its title track was the effort’s biggest hit, peaking at No. 8 on the Hot 100 that summer – assisted by a music video showing the star in a leggy feather leotard, writhing sensuously in a bird cage – but public interest in the rest of the album petered out quickly, and Cyrus would disavow it as her “last pop record” soon afterward. In January 2011, Hannah Montana’s final season finished airing, and its soundtrack became the show’s first to not break the top 10 on the albums chart. Miley took a break from music to focus on acting, filming the Nicholas Sparks tear-jerker The Last Song (during which she met future ex-husband and frequent muse, Liam Hemsworth), detective comedy So Undercover and teen romance LOL over the course of two years. 

But let’s get back to hair. Cyrus’ signature brunette waves were aesthetically quintessential to the Miley-Hannah package. That’s why it was so shocking when the star shaved the sides of her head in August 2012 and bleached the scruff that remained on top. Miley Stewart – and certainly Hannah Montana – were long gone. Cyrus tweeted, “Never felt more me in my whole life.” 

The makeover was the first domino in a pop culture-disrupting series of events and a full metamorphosis for Cyrus, who still wouldn’t reach legal drinking age until November 2013. In March of that year, she posted a video of her twerking to J. Dash and Flo Rida’s “WOP” in a unicorn onesie. In June, she dropped “We Can’t Stop,” a Mike Will Made-It production originally penned for Rihanna. The hedonistic, anti-polite-society earworm and its music video were both massive year-defining hits, with the track reaching No. 2 on the Hot 100 and the Diane Martel-directed visual deliberately showing Cyrus in the most extreme anti-Hannah light possible: shaking her ass at a grimy house party, making out with a doll in a swimming pool full of nearly naked friends, wagging her tongue Gene Simmons-style and repeatedly flashing her grill to the camera.  

In August, she caused nothing short of nationwide panic by grinding on Robin Thicke and miming sex on a foam finger at the VMAs, earning bemused looks from Rihanna and One Direction in the audience that were nothing compared to the horrified outcries from parents and think piece writers everywhere the next day. It sparked months – years, even – of discourse surrounding Cyrus’ body, the children she’d supposedly scarred and whether she was mentally “disturbed,” as MSNBC anchor Mika Brzezinski put it at the time. Her “stripper pole” incident in 2009 now seemed like child’s play.  

In September, she swung butt-naked on a demolition ball and made out with a sledgehammer in the since-disgraced Terry Richardson-directed “Wrecking Ball” music video, leading the late Sinead O’Connor to urge Cyrus to stop “pimping” herself in an open letter. In October, she unblinkingly said that Hannah Montana “was murdered” while hosting Saturday Night Live. 

Miley Cyrus

John Shearer/Getty Images

You could say Cyrus was overcompensating. You could say she was being raunchy just for the sake of being raunchy. You could definitely say that she was appropriating and caricaturing Black culture, a critique that would plague her career for years to come.  

But you can’t say that it wasn’t working: “Wrecking Ball” became her first No. 1 hit on the Hot 100, topping the chart for three weeks, and album Bangerz debuted atop the Billboard 200 with assists from Nelly, Future, French Montana, Ludacris and Cyrus’ oft-claimed predecessor, Britney Spears. The corresponding world tour grossed a reported $63 million in 2014, according to Billboard Boxscore. Love it or hate it, the era remains one of the most commercially successful and iconic of her career, so much so that Billboard’s staff named her the Greatest Pop Star of 2013. 

“I know what I’m doing,” she told Rolling Stone at the time. “I know I’m shocking you.” 

From there, Cyrus embraced her role as provocateur, raving about her love of smoking weed and taking molly and appearing on late night shows with heart-shaped pasties covering her nipples. She also discovered new passions outside of music and acting. Fueled by the attention she so easily captured with her and Thicke’s NSFW performance, Cyrus began her Happy Hippie Foundation in 2014 — “If the world is going to focus on me and what I am doing, then what I am doing should be impactful and it should be great,” she told Wonderland — dedicated to helping homeless and LGBTQ+ youth. The next year, she returned to the VMAs as host, which had some hiccups (“Miley, what’s good?”) but seemed like something she truly enjoyed doing; seven years later, she’d host Miley’s New Year’s Eve Party with her famous godmother for NBC.  

During the 2015 ceremony, she would also announce her psychedelic LP Miley Cyrus & Her Dead Petz, having severed ties with Dr. Luke amid his legal battle with Kesha. Seemingly rebuking the spotlight she’d earned with Bangerz, Cyrus dropped the album for free on SoundCloud before making it available commercially with new label RCA Records much later. The record was panned by critics and ineligible for chart consideration, but ended up being a wise move even disregarding its retroactive love from fans down the line; with Dead Petz, Cyrus effectively cleaned her slate to do whatever she wanted next without the pressure of matching Bangerz’s commercial success. 

Miley Cyrus

Jason Merritt/Getty Images

In 2016, she came out as pansexual, a major moment of visibility for the LGBTQ community considering her conservative Disney Channel roots. “My first relationship in my life was with a chick,” she told Variety. “I grew up in a very religious Southern family … Once I understood my gender more, which was unassigned, then I understood my sexuality more. I was like, ‘Oh — that’s why I don’t feel straight and I don’t feel gay. It’s because I’m not.’” 

Either satisfied that she’d made her point or having simply outgrown her rebellious phase, Cyrus calmed down a bit in the mid-to-late 2010s. But she would spend her next few albums trying to reckon with her past behavior, starting with 2017’s Younger Now, a lighter album partly inspired by her newfound domestic bliss with Hemsworth, whom she married the following year. On the title track, she made a point of explaining that she’d moved on from grinding on Teddy bears and straddling giant hot dogs —  “No one stays the same … what goes up must come down” — and in the serene beachside music video for lead single “Malibu,” she appeared with her bleached hair symbolically growing out to reveal her natural brown roots. The project peaked at No. 5 on the Billboard 200, a new low for Cyrus, and barely eked out a top 10 hit with “Malibu.”  

After scrapping a planned three-EP rollout after its first installment, She Is Coming – the highlight of which was “Slide Away,” an ode to her pending split from Hemsworth — Cyrus again wrestled with her past on Plastic Hearts. “They told me I should cover [my body], so I went the other way,” she sang on “Golden G String.” “I was trying to own my power, still I’m trying to work it out.” It was during this era that Cyrus embraced rock music – marked, of course, by her edgy blonde mullet – a style that was arguably a better fit for her than pop ever had been, artistically speaking. Though not her most commercially successful album, she proved herself in other ways, holding her own in the booth next to the LP’s special guests Billy Idol, Joan Jett and Stevie Nicks and earning viral moments for her exquisite Blondie and Cranberries covers. 

Over these years, she also set a new precedent for herself when it came to touring: With the Bangerz trek marking her most recent proper solo headlining tour to date, Miley opted not to tour at all for Younger Now and performed only a limited run of festival dates for Plastic Hearts, preferring instead to give fans live numbers through her years-long Backyard Sessions series. For someone whose life was so heavily regimented by other people when she was young, there’s no doubt that shirking the traditional touring model was an especially meaningful boundary for her to set on her own behalf in adulthood.  

In 2023, years after it seemed Cyrus might never again score a smash as huge as “Wrecking Ball,” she circled back to a more straightforward pop sound on Endless Summer Vacation (via new label Columbia Records) and found runaway success with lead single “Flowers.” The Bruno Mars-echoing, Hemsworth-teasing track spent eight weeks at No. 1 on the Hot 100 and earned Cyrus best pop solo performance — her first-ever Grammy — at the 2024 awards, as well as record of the year. On final single “Used to Be Young,” she once again addressed her past: “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.” 

Cyrus has already lived multiple lives in her nearly-two-decade career — from tween idol to pop rabble-rouser to rock star and everything else in between – but now, the label that suits Miley best at age 31 is simply seasoned professional. Her versatile talents are sought out by many in the industry, from Beyoncé on Cowboy Carter duet “II Most Wanted” to acclaimed indie studio A24 on a recent cover of Talking Heads’ “Psycho Killer.” And the little girls she raised as Hannah Montana make up the next generation of stars, from Sabrina Carpenter — who at 10 years old won a fan contest to meet Miley — to Chappell Roan, whose fandom of the Disney Channel show inspired her own sparkly alter ego.  

In 2024, Cyrus seems especially at peace, with both her past and who she is now. And after years of the world struggling to catch up to her, it seems the culture – far less uptight than it was when she entered it, thanks in part to her so loudly disavowing the standards of sensibility we used to force on female artists – is finally giving the singer credit for leaving such a lasting impression. 

In an emotional full-circle moment, Cyrus got the rare chance to bask in that recognition at the Disney Legends Ceremony in August. Tearfully facing the crowd with her hair mostly brunette for the first stretch since 2013 – aside from a few streaks of blonde highlight, perhaps showing that all her past selves will always be with her in some capacity – she said that “a little bit of everything has changed” since she first donned her famous wig in 2005. 

“But at the same time, nothing has changed at all,” Cyrus continued. “I stand here still proud to have been Hannah Montana. Because she made Miley in so many ways.” 

Read more about the Greatest Pop Stars of the 21st Century here — and be sure to check back on Thursday when our No. 14 artist is revealed!