Best Pop Singers of 21st Century (No. 15)

With the primary quarter of the twenty first century coming to a detailed, Billboard is spending the subsequent few months counting down our workers picks for the 25 biggest pop stars of the final 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 bear in mind the century in Miley Cyrus — who at age 31 has already lived via a number of inventive lifetimes, producing quite a few pop classics and numerous unforgettable moments within the course of.

For a lot of artists, it’s their hit songs, pop culture-defining albums or chart successes which might be best to pinpoint as landmarks for essentially the most pivotal phases of their careers. However for Miley Cyrus, it’s hair. 

Although she definitely has loads of all of the above accomplishments, the 31-year-old generational expertise’s phases of life have at all times been irrevocably intertwined with what’s occurring atop her head — from the blonde wig that made her well-known within the mid 2000s to the bleached pixie minimize that launched the world to a really completely different Miley in 2012. It goes past the general public’s obsession with magnificence requirements, which a skinny, blue-eyed Cyrus would embody for the primary a number of years of her profession earlier than rejecting that mildew altogether; the singer’s hair has had a manner of symbolizing the place she’s at personally and artistically through the years.   

And the place she’s been, in each regards, has been all around the map. From keen Disney Channel prodigy to unruly pop outlaw, freewheeling style experimenter and mature trendy hitmaker, Cyrus’ knack for earnest reinvention has sustained her via all of the peaks and valleys of her profession. With no scarcity of chart hits and much more iconic culture-shocking moments, she’s endured as one of many century’s most important pop stars – as a result of it doesn’t matter what model she’s making an attempt out, on the finish of the day, she’s at all times nonetheless simply being Miley. 

Born Future Hope Cyrus on Nov. 23, 1992, within the Nashville metropolitan space of Tennessee, essentially the most recognizable head of hair within the younger star’s childhood wasn’t her personal, however father Billy Ray’s signature mullet. Miley, who legally adopted her childhood nickname in 2008, grew up in a constellation of different stars earlier than she would turn out to be one herself, together with her dad turning into a rustic sensation within the ’90s for the huge crossover hit “Achy Breaky Coronary heart” and her godmother being none aside from Dolly Parton.

Seeing Billy Ray act on his early-’00s medical drama Doc impressed Miley to wish to be a performer, too, main her to audition for Disney Channel’s Hannah Montana at simply 12 years previous. After first studying for the a part of sidekick Lily, the preteen was as an alternative requested to attempt for the sitcom’s important character as an alternative: Miley Ray Stewart, a Malibu teen who may rework at any second to international pop sensation Hannah Montana, with a wig that someway carried the identical camouflaging powers as Clark Kent’s glasses. Billy Ray was forged as her character’s dad, their pure chemistry translating superbly on display screen.  

It’s exhausting to explain simply how magnetic Cyrus was on that present. Right here was a woman who may ship a tacky catch phrase — normally “Candy niblets!” or  “Yeeee doggies!” — like a seasoned comedic actor, unafraid of showing unattractive or goofy in service of bit with an innate energy and resonance in her voice that was nearly unnatural for her age. 

And also you’d higher imagine that Disney capitalized on her uncooked expertise. Throughout Hannah Montana’s run from 2006 to 2011, the kids’s community churned out 4 seasons of TV, 5 soundtrack albums, a function movie, a tour and a live performance film — to not point out numerous clothes strains, lunch packing containers, backpacks, equipment, make-up, blankets, throw pillows and Completely happy Meal toys plastered with Miley and Hannah’s shared face.  

All of the whereas, Cyrus was basically holding down two music careers without delay, signing with Walt Disney Data for all issues Hannah after which with Hollywood Data for her personal work as Miley. Her first two albums, Hannah Montana and Hannah Montana 2/Meet Miley Cyrus each debuted at No. 1 on the Billboard 200. On the Better of Each Worlds Tour, she carried out one half as herself and the opposite as her alter ego (the trek grossed greater than $54 million, in accordance with Billboard Boxscore). She scored quite a few chart hits below Hannah — “Better of Each Worlds,” “No person’s Good” and 18 extra tracks made the Billboard Sizzling 100 in the course of the present’s run – which gave solution to extra hits as Miley. Each “See You Once more” and the Nick Jonas breakup anthem “7 Issues” reached the Sizzling 100 prime 10 and gave her credibility outdoors of the Disneyverse, main pop followers to begin taking her critically outdoors of her lane as a youngsters’ TV star.   

As Miley and Hannah turned more and more inextricably linked, nevertheless, it obtained more durable for the general public to detangle Miley Cyrus from Hannah Montana, and even from Miley Stewart. Actions like posing bare-shouldered on the duvet of Vainness Truthful in 2008 or hitting a salvia bong the week of her 18th birthday in 2010 weren’t the mere antics of a maturing teenage woman, they had been affronts to a squeaky-clean, million-dollar model depending on the adoration of little youngsters and the approval of their dad and mom. This left Cyrus with few choices for mapping out her profession post-Hannah: danger spending the remainder of her life dwelling in her personal character’s shadow or management the narrative by inelegantly demolishing that character and forcing the world to observe. Everyone knows which route she selected – however first, makes an attempt at a extra seamless transition had been made.  

In 2009, the identical 12 months Sizzling 100 No. 4 hit ballad “The Climb” and barn-raising dance tune “Hoedown Throwdown” got here out for Hannah Montana: The Film’s soundtrack, Cyrus dropped the 7-track EP The Time of Our Lives, that includes what continues to be considered one of her most beloved and simply recognizable hits: “Social gathering in the usA.” The Dr. Luke-produced quasi-patriotic banger instantly turned Cyrus’ greatest dwelling run thus far, exploding on pop radio and reaching No. 2 on the Sizzling 100 because of its charming lyrics and infectious important hook. (Significantly, how does one not sing alongside to that “Yeah-ee-ah-ee-ah-ee-ah” within the refrain?) The observe additionally provided a glimpse at what her post-Disney pop music profession would possibly’ve seemed like for the subsequent decade if she’d needed it: polished, extensively palatable and carried out by the identical Miley Hannah Montana followers knew and liked, simply with a extra mature sound and possibly barely shorter shorts

However then, she obtained on stage at that 12 months’s Teen Selection Awards and innocently carried out the observe on prime of a prop ice cream cart, holding onto a silver bar in order to not fall off whereas dancers pushed her round. Besides, the lots didn’t see it that manner: The showcase sparked international gasps and pearl-clutching over what scandalized audiences interpreted as a risqué pole dance. One well-known tabloid headline requested if Miley was “turning into Britney.” As a substitute of coming to her protection, her community shortly launched a press release: “Disney Channel gained’t be commenting on that efficiency, though dad and mom can relaxation assured that every one content material introduced on the Disney Channel is age-appropriate for our viewers – youngsters 6-14 – and in keeping with what our model values are.” (This is the reason we will’t have good issues.) .  

After that, Miley got here again with 2010’s Can’t Be Tamed, an album meant to showcase her edgier aspect and her final with Hollywood Data. Its title observe was the trouble’s greatest hit, peaking at No. 8 on the Sizzling 100 that summer season – assisted by a music video displaying the star in a leggy feather leotard, writhing sensuously in a hen cage – however public curiosity in the remainder of the album petered out shortly, and Cyrus would disavow it as her “final pop document” quickly afterward. In January 2011, Hannah Montana’s remaining season completed airing, and its soundtrack turned the present’s first to not break the highest 10 on the albums chart. Miley took a break from music to concentrate on performing, filming the Nicholas Sparks tear-jerker The Final Tune (throughout which she met future ex-husband and frequent muse, Liam Hemsworth), detective comedy So Undercover and teenage romance LOL over the course of two years. 

However let’s get again to hair. Cyrus’ signature brunette waves had been aesthetically quintessential to the Miley-Hannah bundle. That’s why it was so surprising when the star shaved the edges of her head in August 2012 and bleached the scruff that remained on prime. Miley Stewart – and positively Hannah Montana – had been lengthy gone. Cyrus tweeted, “By no means felt extra me in my entire life.” 

The makeover was the primary domino in a pop culture-disrupting collection of occasions and a full metamorphosis for Cyrus, who nonetheless wouldn’t attain authorized ingesting age till November 2013. In March of that 12 months, she posted a video of her twerking to J. Sprint and Flo Rida’s “WOP” in a unicorn onesie. In June, she dropped “We Can’t Cease,” a Mike Will Made-It manufacturing initially penned for Rihanna. The hedonistic, anti-polite-society earworm and its music video had been each large year-defining hits, with the observe reaching No. 2 on the Sizzling 100 and the Diane Martel-directed visible intentionally displaying Cyrus in essentially the most excessive anti-Hannah gentle doable: shaking her ass at a dirty home social gathering, making out with a doll in a swimming pool stuffed with practically bare mates, wagging her tongue Gene Simmons-style and repeatedly flashing her grill to the digicam.  

In August, she brought about nothing in need of nationwide panic by grinding on Robin Thicke and miming intercourse on a foam finger on the VMAs, incomes bemused seems from Rihanna and One Path within the viewers that had been nothing in comparison with the horrified outcries from dad and mom and assume piece writers in every single place the subsequent day. It sparked months – years, even – of discourse surrounding Cyrus’ physique, the kids she’d supposedly scarred and whether or not she was mentally “disturbed,” as MSNBC anchor Mika Brzezinski put it on the time. Her “stripper pole” incident in 2009 now appeared like youngster’s play.  

In September, she swung butt-naked on a demolition ball and made out with a sledgehammer within the since-disgraced Terry Richardson-directed “Wrecking Ball” music video, main the late Sinead O’Connor to induce Cyrus to cease “pimping” herself in an open letter. In October, she unblinkingly stated that Hannah Montana “was murdered” whereas internet hosting Saturday Evening Reside. 

You might say Cyrus was overcompensating. You might say she was being raunchy only for the sake of being raunchy. You might undoubtedly say that she was appropriating and caricaturing Black tradition, a critique that may plague her profession for years to return.  

However you’ll be able to’t say that it wasn’t working: “Wrecking Ball” turned her first No. 1 hit on the Sizzling 100, topping the chart for 3 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, in accordance with Billboard Boxscore. Like it or hate it, the period stays probably the most commercially profitable and iconic of her profession, a lot in order that Billboard’s workers named her the Best Pop Star of 2013. 

“I do know what I’m doing,” she advised Rolling Stone on the time. “I do know I’m surprising you.” 

From there, Cyrus embraced her function as provocateur, raving about her love of smoking weed and taking molly and showing on late evening exhibits with heart-shaped pasties overlaying her nipples. She additionally found new passions outdoors of music and performing. Fueled by the eye she so simply captured together with her and Thicke’s NSFW efficiency, Cyrus started her Completely happy Hippie Basis in 2014 — “If the world goes to concentrate on me and what I’m doing, then what I’m doing ought to be impactful and it ought to be nice,” she advised Wonderland — devoted to serving to homeless and LGBTQ+ youth. The following 12 months, she returned to the VMAs as host, which had some hiccups (“Miley, what’s good?”) however appeared like one thing she really loved doing; seven years later, she’d host Miley’s New 12 months’s Eve Social gathering together with her well-known godmother for NBC.  

Throughout the 2015 ceremony, she would additionally announce her psychedelic LP Miley Cyrus & Her Lifeless Petz, having severed ties with Dr. Luke amid his authorized battle with Kesha. Seemingly rebuking the highlight she’d earned with Bangerz, Cyrus dropped the album without spending a dime on SoundCloud earlier than making it out there commercially with new label RCA Data a lot later. The document was panned by critics and ineligible for chart consideration, however ended up being a sensible transfer even disregarding its retroactive love from followers down the road; with Lifeless Petz, Cyrus successfully cleaned her slate to do no matter she needed subsequent with out the stress of matching Bangerz’s business success. 

In 2016, she got here out as pansexual, a serious second of visibility for the LGBTQ neighborhood contemplating her conservative Disney Channel roots. “My first relationship in my life was with a chick,” she advised Selection. “I grew up in a really non secular Southern household … As soon as I understood my gender extra, which was unassigned, then I understood my sexuality extra. I used to be like, ‘Oh — that’s why I don’t really feel straight and I don’t really feel homosexual. It’s as a result of I’m not.’” 

Both glad that she’d made her level or having merely outgrown her rebellious part, Cyrus calmed down a bit within the mid-to-late 2010s. However she would spend her subsequent few albums making an attempt to reckon together with her previous habits, beginning with 2017’s Youthful Now, a lighter album partly impressed by her newfound home bliss with Hemsworth, whom she married the next 12 months. On the title observe, she made some extent of explaining that she’d moved on from grinding on Teddy bears and straddling large scorching canines —  “Nobody stays the identical … what goes up should come down” — and within the serene beachside music video for lead single “Malibu,” she appeared together with her bleached hair symbolically rising out to disclose her pure brown roots. The mission peaked at No. 5 on the Billboard 200, a brand new low for Cyrus, and barely eked out a prime 10 hit with “Malibu.”  

After scrapping a deliberate three-EP rollout after its first installment, She Is Coming – the spotlight of which was “Slide Away,” an ode to her pending cut up from Hemsworth — Cyrus once more wrestled together with her previous on Plastic Hearts. “They advised me I ought to cowl [my body], so I went the opposite manner,” she sang on “Golden G String.” “I used to be making an attempt to personal my energy, nonetheless I’m making an attempt to work it out.” It was throughout this period that Cyrus embraced rock music – marked, after all, by her edgy blonde mullet – a mode that was arguably a greater match for her than pop ever had been, artistically talking. Although not her most commercially profitable album, she proved herself in different methods, holding her personal within the sales space subsequent to the LP’s particular company Billy Idol, Joan Jett and Stevie Nicks and incomes viral moments for her beautiful Blondie and Cranberries covers. 

Over these years, she additionally set a brand new precedent for herself when it got here to touring: With the Bangerz trek marking her most up-to-date correct solo headlining tour thus far, Miley opted to not tour in any respect for Youthful Now and carried out solely a restricted run of pageant dates for Plastic Hearts, preferring as an alternative to offer followers dwell numbers via her years-long Yard Periods collection. For somebody whose life was so closely regimented by different folks when she was younger, there’s little question that shirking the standard touring mannequin was an particularly significant boundary for her to set on her personal behalf in maturity.  

In 2023, years after it appeared Cyrus would possibly by no means once more rating a smash as large as “Wrecking Ball,” she circled again to a extra simple pop sound on Infinite Summer time Trip (through new label Columbia Data) and located runaway success with lead single “Flowers.” The Bruno Mars-echoing, Hemsworth-teasing observe spent eight weeks at No. 1 on the Sizzling 100 and earned Cyrus greatest pop solo efficiency — her first-ever Grammy — on the 2024 awards, in addition to document of the 12 months. On remaining single “Used to Be Younger,” she as soon as once more addressed her previous: “I do know I was loopy, I do know I was enjoyable/ You say I was wild, I say I was younger.” 

Cyrus has already lived a number of lives in her nearly-two-decade profession — from tween idol to pop rabble-rouser to rock star and every thing else in between – however now, the label that fits Miley greatest at age 31 is just seasoned skilled. Her versatile abilities are sought out by many within the business, from Beyoncé on Cowboy Carter duet “II Most Needed” to acclaimed indie studio A24 on a latest cowl of Speaking Heads’ “Psycho Killer.” And the little women she raised as Hannah Montana make up the subsequent era of stars, from Sabrina Carpenter — who at 10 years previous gained a fan contest to satisfy Miley — to Chappell Roan, whose fandom of the Disney Channel present impressed her personal sparkly alter ego.  

In 2024, Cyrus appears particularly at peace, with each her previous and who she is now. And after years of the world struggling to catch as much as her, it appears the tradition – far much less uptight than it was when she entered it, thanks partly to her so loudly disavowing the requirements of sensibility we used to power on feminine artists – is lastly giving the singer credit score for leaving such an enduring impression. 

In an emotional full-circle second, Cyrus obtained the uncommon probability to delight in that recognition on the Disney Legends Ceremony in August. Tearfully going through the gang together with her hair principally brunette for the primary stretch since 2013 – apart from a number of streaks of blonde spotlight, maybe displaying that every one her previous selves will at all times be together with her in some capability – she stated that “just a little little bit of every thing has modified” since she first donned her well-known wig in 2005. 

“However on the similar time, nothing has modified in any respect,” Cyrus continued. “I stand right here nonetheless proud to have been Hannah Montana. As a result of she made Miley in so some ways.” 

Learn extra in regards to the Best Pop Stars of the twenty first Century right here — and make sure to examine again on Thursday when our No. 14 artist is revealed!