Entertainment Music Pop Music The Evolution of Miley Cyrus, from Hannah Montana to Grammy Winner to Becoming the Youngest Disney Legend Look back at Miley's always surprising — and often shocking — changes over her two-decade career By Sophie Dodd Sophie Dodd Sophie Dodd is a freelance writer for PEOPLE. She previously worked as an editorial assistant at PEOPLE from 2018 to 2022. People Editorial Guidelines and Brendan Le Brendan Le Brendan Le is an Editorial Assistant at PEOPLE with three years of experience working as an editor and writer. People Editorial Guidelines Updated on August 13, 2024 06:24PM EDT Close Miley Cyrus. Photo: Byron Cohen/Disney Channel/Getty; The Walt Disney Company In 2006, Miley Cyrus donned a blonde wig and changed her life. Little did she know, Cyrus would also become one of the most recognizable figures of her generation and a cultural icon apart of many people's childhoods. For five years, the Disney Channel child star led Hannah Montana as the eponymous pop star living a double life. Following the series finale in January 2011, Cyrus adopted her famous character's occupation and launched a successful music career that included several of the 2010s' most memorable pop culture moments. With eight studio albums, two Grammy Awards and two No. 1 songs on the Billboard Hot 100, Cyrus has established herself as a bonafide music icon and recently became the youngest person to be named a Disney Legend. Still, her journey to get there hasn't always been smooth sailing. See Cyrus' evolution over the last two decades, from a wee Disney starlet to an official Disney Legend. 01 of 33 Her Double Life on 'Hannah Montana' Disney Channel/Courtesy Everett Collection Before she was an international superstar, Miley Cyrus was just being Miley Stewart — a middle school girl who once awkwardly rubbed ketchup on her crush's hands and claimed it was a great moisturizer. Her lead role as a normal girl living a double life as a pop star on Disney Channel's Hannah Montana made the then-13-year-old Cyrus a household name. 02 of 33 Her Struggles with Body Image Bob D'Amico/Disney/Courtesy Everett Collection Her time on Hannah Montana — which ran until 2011 — and the pressure of being a role model for young girls while still trying to figure out her own identity were part of what later propelled Cyrus to rebel against her Disneyfied image. "From the time I was 11, it was, 'You're a pop star! That means you have to be blonde, and you have to have long hair, and you have to put on some glittery tight thing,' " Cyrus explained to Marie Claire in 2015. "Meanwhile, I'm this fragile little girl playing a 16-year-old in a wig and a ton of makeup. It was like Toddlers & Tiaras." "I was made to look like someone that I wasn't, which probably caused some body dysmorphia, because I had been made pretty every day for so long, and then when I wasn't on that show, it was like, 'Who the f— am I?' " she told the magazine. 03 of 33 Her Breakover Style Lester Cohen/WireImage Early romances were also formative to Cyrus' frequent style transformations. After her two-year relationship with fellow Disney star Nick Jonas came to an end in late 2007 (and blessed us with the iconic teenage breakup anthem, "7 Things"), 15-year-old Cyrus made one of her first big beauty changes. "When we were dating, Nick wanted me to get highlights — and so I did that, and I got myself looking great," she revealed in an interview with Seventeen. "And then, on the day we broke up, I was like, 'I want to make my hair black now — I don't want to look pretty; I want to look hard-core.' I was rebelling against everything Nick wanted me to be. And then I was like, 'I've got to be by myself for now and just figure out who I really am.' " 04 of 33 Her Meet-Cute with Liam on the Set of 'The Last Song' The Last Song. Touchstone/Kobal/REX/Shutterstock Cyrus continued to balance her career as a singer and actress, making the leap to the big screen to star in 2010's The Last Song opposite her now ex-husband Liam Hemsworth. The two met while filming and made their official debut as a couple just before the movie's premiere, much to the delight of fans and believers in true love everywhere. 05 of 33 Her 'Can't Be Tamed' Music Video A few months after The Last Song premiered, Cyrus released Can't Be Tamed, an album that marked the start of her transition away from her wholesome child star image. The music video for the album's titular single featured the singer dressed up like a rare bird and dancing in a cage while a mob of people ogled and photographed her, sending a message to fans and haters alike: "I want to be a part of something I don't know/ And if you try to hold me back I might explode … I can't be tamed/ I can't be blamed." Cyrus let the world know loud and clear that she was ready to break out of her cage. 06 of 33 Her Provocative Performance at the 2013 VMAs Jeff Kravitz/FilmMagic Cyrus' infamous foam finger ride and nearly nude twerking performance with Robin Thicke at the 2013 MTV Video Music Awards catapulted her to new levels of controversy — but shocking audiences quickly became standard fare for the "We Can't Stop" singer. Soon after her performance, she and Hemsworth — who had announced their engagement in June of 2012 after years of dating on and off — called it off, although the pair kept in contact. But the performance also helped her grow and realize her potential to reach people, she later revealed in an interview with Wonderland magazine in early 2018. "Not only was culture changed, but my life and career were changed forever," she told the outlet. "It inspired me to use my platform for something much bigger. 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." 07 of 33 Her 'Wrecking Ball' Music Video What better way to literally and metaphorically destroy your child star image than swinging in naked on a wrecking ball? In what immediately became one of the most iconic music videos of all time, Cyrus' 2013 hit didn't exactly wipe her slate clean, but it did usher in the era of Bangerz Miley. House party vibes were front and center on the album, and further backlash ensued as Cyrus began crossing over into hip-hop culture in both her music and style, with fans and critics calling the singer out for what they saw as cultural appropriation. 08 of 33 Her Acts of Activism Frazer Harrison/Getty The year after her provocative performance with Thicke, Cyrus returned to the 2014 VMAs and shocked fans in an entirely different way — by turning the spotlight away from herself and onto Jesse Helt, a young homeless man she brought as her date for the evening to raise awareness for homeless youth. Helt accepted the video of the year award for "Wrecking Ball" on Cyrus' behalf and used the moment to speak about the cause. The following month, the singer founded The Happy Hippie Foundation, a non-profit organization focused on standing up for homeless youth and the LGBTQ community. 09 of 33 Her Runway Moment Joe Kohen/Getty Cyrus briefly added "model" to her list of professions when she walked the runway at the Jeremy Scott Spring 2015 fashion show alongside the designer himself. 10 of 33 Her Looks as Host of the 2015 VMAs Frank Trapper/Corbis via Getty Fast-forward to the 2015 VMAs, and the spotlight was most definitely back on Cyrus, who hosted the show. Styled by Simone Harouche, the singer debuted her new over-the-top performance style, sporting blonde dreads and dressed in a silver harness that covered only the center of her breasts, with a skirt that dripped down from it like a chandelier. 11 of 33 Her New Performance Style Kevork Djansezian/Getty Cyrus dropped her free Miley Cyrus and Her Dead Petz album on Aug. 30, 2015, the same day as the VMAs. Her multiple costume changes — from a glittery multi-colored leotard to a truly impressive array of eccentric hair accessories — were just a taste of the outrageous looks to come during her album tour. 12 of 33 Her Dead Petz Era Jeff Kravitz/FilmMagic Her looks on tour ran the gamut from playful yet bizarre — a giant sunshine, a stick of butter — to full-on jaw-dropping, including exposed fake breasts and giant strap-ons. 13 of 33 Her Onstage Antics From the psychedelic tunes to her extreme looks, the tour further set Cyrus apart as an artist who defies categorization. 14 of 33 Her Gig on 'The Voice' Trae Patton/NBC/Getty In March 2016, 23-year-old Cyrus announced her newest gig — that she would be joining season 11 of The Voice as a judge and key advisor to aspiring singers. Her new role saw her in tamer looks, seemingly marking the end of the Dead Petz era. 15 of 33 Her Just Being Miley Courtesy Miley Cyrus But don't worry — there was still plenty of sparkle and her signature tongue-out smile to go around. 16 of 33 Her Smoking Stage Miley Cyrus/Instagram And Cyrus' affinity for smoking weed was still in 'high' gear at the time. The "Bangerz" singer frequently documented her use of the substance on Instagram, sharing photos of herself with a joint while cuddling with her menagerie of pets. 17 of 33 Her Change of Heart Miley Cyrus/Instagram She eventually took a long hiatus from smoking in order to focus on her 2017 album Younger Now, until she admitted in December 2018 that her mom, Trish Cyrus, had reintroduced her to the substance — but in a more manageable way. "My mom got me back on it," she revealed to The Sun. "When I'm just working, I don't think I function at my highest, most intelligent, most being-able-to-be-as-aware-and-as-present, so I don't smoke when I work." "I stopped smoking because to sit here and to talk about what I'm doing. I wanted to be really clear because I'm actually the most passionate about what I'm doing with this record," Cyrus told Jimmy Fallon on The Tonight Show. "This record for me at this moment is the most important album that I've ever made and so I wanted to make sure I'm super clear about the way I'm talking." 18 of 33 Her 'Younger Now' Era Broadimage/REX/Shutterstock In 2017, Cyrus released her album Younger Now, which saw the star again forging a new path for herself and embracing her Nashville roots. "For Bangerz I was so one way, and I did that on Dead Petz too," she told NME Magazine. " 'Malibu' and 'Younger Now' are obviously two very different visuals in a way, but what binds them together is that they are both me. Now, I think I have more of an open mind." Cyrus admitted to the outlet that she recognized Dead Petz isn't "a record for everyone," and she made sure not to make "people less mentally available to listen" to her music when working on her Younger Now. 19 of 33 Her Boho 'Malibu' Style The "Malibu" singer's new rootsy phase also saw a major shift in her style to match, with the star shedding her rainbow wigs and bedazzled looks for a more bohemian-meets-country vibe. "The craziest thing I can do now is go on Fallon in jeans and a T-shirt. Not because I want to 'act normal,' but because that's really what I wear," she explained to Billboard. 20 of 33 Her Thoughts on Her Personal Evolution Sam Wasson/Getty Still, Cyrus stayed true to herself, refusing to fit into any one mold. "I think I show people that they can be themselves," she told Harper's Bazaar in the magazine's August 2017 cover story. "I also think something that has been important for me, in this next little, like, transition phase of my career is that I don't give a f— about being cool. I just want to be myself." "People get told that it's a bad thing to change," she told the magazine. Cyrus thinks, however, "you are supposed to change all the time." 21 of 33 Her Performance at the 2018 Grammy Awards Jeff Kravitz/FilmMagic For the 2018 Grammys, Cyrus further wowed fans with her shift to old-Hollywood glamour during her duet with Elton John to perform his song "Tiny Dancer." Ahead of the show, John opened up about finally performing with Cyrus. "I've always loved her. I like those kind of women," John told Ryan Seacrest on the E! red carpet. "I like my women to be strong, I like them to be feisty and she's certainly that! And she can sing so it's finally great to work with her." 22 of 33 Her Rekindled Romance (and Engagement!) with Liam Newscom/Zuma In early 2016, Cyrus and Hemsworth rekindled their on-again, off-again romance, announcing that they were once again engaged. 23 of 33 Her Met Gala Moment John Shearer/Getty Cyrus continued to show off her new sophisticated style at the 2018 Met Gala. The famous animal lover made a statement in a stunning black gown by Stella McCartney, who is known for her animal-friendly designs. 24 of 33 Her 'Nothing Breaks Like a Heart' Music Video Back at it! In November 2018, Cyrus released her first single in over a year, a futuristic country-tinged tune called "Nothing Breaks Like a Heart," the lead single off of Mark Ronson's latest album, his first solo album in nearly four years. 25 of 33 Her Secret Wedding to Liam Miley Ray Cyrus/Twitter Cyrus continues to be full of surprises, which should no longer really come as a surprise to fans. She and Hemsworth secretly tied the knot in December 2018, after meeting nearly a decade prior while filming opposite each other in The Last Song. "This is probably our one – millionth kiss," the singer captioned a shot of the newlyweds sharing a passionate smooch. 26 of 33 And Her Subsequent Split Chelsea Lauren/WWD/Shutterstock Less than one year after their wedding, the pair announced their split in August 2019. "Liam and Miley have agreed to separate at this time," a rep for Cyrus tells PEOPLE in a statement. "Ever-evolving, changing as partners and individuals, they have decided this is what's best while they both focus on themselves and careers. They still remain dedicated parents to all of their animals they share while lovingly taking this time apart. Please respect their process and privacy." 27 of 33 Her Rebound Suzy Creamcheese / SplashNews.com As the split news shook fans, Cyrus jetted off to Italy with her sister and Brody Jenner's ex-wife, Kaitlynn Carter. The two were photographed kissing during their getaway, and came back to the U.S. in a highly publicized, whirlwind romance. 28 of 33 Her New Boo Miley Cyrus and Cody Simpson. Miley Cyrus Instagram After her split from Carter, Cyrus started seeing longtime friend and fellow musician Cody Simpson. "Miley and Cody have their separate lives," a source told PEOPLE in November 2019. "Cody had to stay in L.A. but has visited Miley in Tennessee. They have a very easy relationship. They see each other when they can, and when they are apart, things are good too. This works for both of them." After 10 months of dating, the pair broke up the following August. 29 of 33 Rockstar Era Miley Cyrus attends the 2020 MTV Video Music Awards on Aug. 30, 2020, in New York City. Vijat Mohindra/MTV VMAs 2020/ In November 2020, Cyrus showed her musical versatility with a pivot into pop rock for her seventh studio album Plastic Hearts. The record, which peaked at No. 2 on the Billboard 200, featured a collaboration with Fleetwood Mac's Stevie Nicks titled "Edge of Midnight." Speaking to Rolling Stone about Plastic Hearts, Cyrus said that music was "the priority" for the album rather than her headline-making actions. When reflecting on the Bangerz era, she said, "The music was driving it, but all those things from that era, ... the pop-culture moments almost eclipse the music itself." 30 of 33 Finding Love Again Miley Cyrus and Maxx Morando. Donato Sardella/Getty Since December 2021, Cyrus has been linked with drummer Maxx Morando after the two were pictured cozying up to each other during the singer's NBC special, Miley's New Year's Eve Party. In February 2024, a source informed PEOPLE that the couple live together and said Cyrus "is very happy with him." "Everyone loves Maxx. He’s a great guy," the source added. "He’s private and doesn’t like being in the press. It’s been good for her.” 31 of 33 Getting Her 'Flowers' On Jan. 13, 2023, Cyrus kickstarted her new album cycle with the lead single "Flowers," which became her biggest hit on the Billboard Hot 100. The song garnered over 100 million streams on Spotify in seven days, breaking the platform's record for the most-streamed song in a week. "Flowers," a part of her eighth studio album Endless Summer Vacation, spent eight weeks at the top of the charts and became the fastest song to surpass one billion streams on Spotify. At the 2024 Grammy Awards, the singer gave a Tina Turner-inspired performance and poked fun at the unenergetic crowd onstage: "Why are y’all acting like y’all don’t know this song?” 32 of 33 Grammy Success Miley Cyrus wins record of the year at the Grammys on Feb. 4, 2024, in L.A. VALERIE MACON/AFP via Getty Images The massive success of "Flowers" translated into two Grammy Awards for Cyrus at the February 2024 ceremony. She took home the iconic gramophone trophy for pop solo performance and record of the year. "This award is amazing. But I really hope that it doesn't change anything because my life was beautiful yesterday. Not everyone in the world will get a Grammy, but everyone in this world is spectacular," Cyrus said in her acceptance speech for record of the year. She added with a laugh, "So please don't think that this is important, even though it's very important, right guys?" 33 of 33 Deemed a Legend Miley Cyrus is named a Disney Legend at D23 on Aug. 11, 2024. The Walt Disney Company At a D23 event in Anaheim, California, Cyrus became the youngest person ever to be named a Disney Legend, a title given to individuals who have significantly influenced the company. Tearing up during her speech, she recalled her path to fame, saying that "a little bit of everything has changed, ... but at the same time, nothing has changed at all." "I stand here still proud to have been Hannah Montana," the Disney alumna continued. "In so many ways, this award is dedicated to Hannah and all of her amazing loyal fans, and to everyone who has made my dream a reality. To quote the legend herself, 'This is the life.' "