Cover Miley Cyrus didn’t just survive the near-impossible transition from child star to respected creative force; she did it on her terms (Photo: Christopher Polk/Billboard/Getty Images)
Miley Cyrus didn’t just survive the near-impossible transition from child star to respected creative force; she did it on her terms (Photo: Christopher Polk/Billboard/Getty Images)
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From Grammy glory to the ‘Hannah Montana Anniversary Special’, here’s the definitive timeline of how Miley Cyrus became one of the most resilient and iconic artists
Miley Cyrus didn’t just grow up in the spotlight; she learned how to bend it to her will. What started as a teen phenomenon turned into something harder to define and much more interesting to watch. Two decades after Hannah Montana made her a household name, she returns to the iconic show with a Disney+ anniversary special that looks back on a career built on risk, reinvention and staying power.
For years, Cyrus fought to be taken seriously after the world had already decided who she was. She made music that divided critics, provoked moral panic and—in quieter, less headline-grabbing moments—left seasoned musicians genuinely speechless. Through it all, she kept reinventing herself, driven by a restlessness that now reads less like rebellion and more like the mark of a true artist.
Today, with Grammy wins, a Golden Globe nomination, a Disney Legend honour and the Hannah Montana 20th Anniversary Special to her name, the question is no longer whether she belongs among entertainment’s greats. Here are the defining moments that prove she always did.
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The double-life phenomenon: selling out arenas as a fictional pop star
Above Miley Cyrus played Miley Stewart, a regular teenager secretly living a double life as international pop star Hannah Montana
When Hannah Montana premiered on March 24, 2006, few predicted the cultural juggernaut it would become. Cyrus played Miley Stewart, a regular teenager secretly living a double life as international pop star Hannah Montana, across four seasons and 98 episodes. The franchise generated three Billboard 200 number-one soundtracks, several multi-platinum certifications and a record-breaking 3D concert film, cementing her as the world’s most powerful teen idol.
Shedding the wig: ‘Can’t Be Tamed’ and the first steps toward independence
Above Miley Cyrus in her ‘Can’t Be Tamed’ era, stepping boldly away from her Disney persona
By 2010, the tension between Miley Cyrus’s maturing identity and Hannah Montana’s pristine constraints was impossible to ignore. Her third studio album, Can’t Be Tamed, arrived with a provocative music video signalling a deliberate break from everything the wig represented. Her starring role in The Last Song, where she met future husband Liam Hemsworth, introduced a strikingly different Miley: complex, romantic and entirely her own.
The ‘Bangerz’ era: the 2013 VMA performance that broke the Internet
Above Miley Cyrus set fire to her once-wholesome image with ‘Bangerz’
Nothing prepared the world for Miley Cyrus at the 2013 MTV Video Music Awards. Twerking alongside Robin Thicke, foam finger in hand, she blew up her former wholesome Hannah Montana image in real time. The Bangerz album followed, a hard pivot into hip-hop and EDM. Then came “Wrecking Ball”, which shattered Vevo records and earned Video of the Year at the 2014 MTV VMAs. Controversy had never been so commercially brilliant.
Finding her true voice: the Backyard Sessions and Happy Hippie philanthropy
Above Miley Cyrus in the Backyard Sessions, showcasing her raw, unfiltered vocal talent
While Bangerz dominated headlines, Cyrus was quietly revealing her greatest asset: her voice. Her 2012 cover of Dolly Parton’s “Jolene”, recorded in her backyard, has amassed over 555 million views and silenced sceptics overnight. In 2014, she channelled this power into the Happy Hippie Foundation, supporting LGBTQ+ youth and tackling homelessness. Sessions with Joan Jett and Laura Jane Grace followed, cementing her rock credibility decisively.
The rock renaissance: ‘Plastic Hearts’ and earning vocal supremacy
Above Miley Cyrus in her ‘Plastic Hearts’ era cemented her rock credibility
During the pandemic, Miley Cyrus leaned into rock, and the world noticed. Her cover of Blondie’s “Heart of Glass” went viral, followed by a breathtaking rendition of The Cranberries’ “Zombie” that was praised by critics. These covers paved the way for her critically acclaimed album Plastic Hearts, proving she wasn’t simply experimenting—she was evolving.
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Grammy vindication: taking home Record of the Year for ‘Flowers’
Above Miley Cyrus took home Best Pop Solo Performance and Record of the Year at the 2024 Grammy Awards
“Flowers” was an era-defining anthem of self-reliance—and the world made it their own. Released in 2023, it propelled Endless Summer Vacation to widespread acclaim. At the 66th Grammy Awards in 2024, Miley Cyrus claimed both Best Pop Solo Performance and the coveted Record of the Year, dressed in a vintage Bob Mackie gown. After two decades of resilience, the industry had finally caught up.
Awards season 2026: ‘Dream As One’ nomination
Above ‘Dream As One’ from ‘Avatar: Fire & Ash’ earned a Best Original Song nomination at the Golden Globes
Miley Cyrus entered 2026 at full velocity. At the Golden Globes, she earned a Best Original Song nomination for “Dream As One” from Avatar: Fire & Ash and presented alongside Pamela Anderson, while at the Grammys, she commanded the red carpet in a black Celine ensemble—a cropped motorcycle jacket adorned with an oversized wreath-and-bouquet pin. The singer was also confirmed as the iHeartRadio Innovator Award recipient.
The next chapter: conceptual artistry and the ‘Something Beautiful’ era
Above Miley Cyrus in the ‘Something Beautiful’ era, proving her reinvention never stops
Just as the Hannah Montana 20th Anniversary Special reminds the world where she began, Cyrus is already signalling where she’s headed. Something Beautiful, her highly stylised, experimental visual concept album, marks an ambitious artistic statement—and earned a nomination for Best Pop Vocal Album at the 2026 Grammys. After 20 years of fearless reinvention, one truth is undeniable: Miley Cyrus has never been content simply to exist. She’s always building the next version of herself.
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After more than a decade in lifestyle media, Clifford has mastered the art of writing seriously about things that are fun—and writing fun things about people who take themselves very seriously. At Tatler Asia, he helped steer its flagship lists, Tatler’s Most Influential and Asia’s Most Stylish. And today, he leads T-Labs, Tatler Asia’s content innovation hub, where he continues the noble pursuit of lifestyle storytelling, spinning stories on wealth, entertainment, necessary style, Hallyu, Hollywood, beauty and more for audiences across Asia.
