Top 20 Good Girl Celebrities Gone Bad
Some stars start their careers with a squeaky clean image and then take a sharp turn into bolder territory as they grow up and take control of their artistry. That shift can show up in riskier roles, new musical directions, or a full style overhaul that leaves their early persona in the rearview.
Here are twenty celebrities who began with a wholesome reputation and later leaned into edgier creative choices. Each entry tracks the concrete milestones that marked the change, from first credits to headline making reinventions that reset how audiences saw them.
Miley Cyrus
Miley Cyrus became a household name on Disney Channel with ‘Hannah Montana’ from 2006 to 2011, a juggernaut that spawned multiplatinum soundtracks, sold out tours, and a feature film release tied to the series. Her early solo albums stayed close to pop rock and teen friendly themes, and she continued to record music while wrapping the show.
In 2013 she pivoted with the Bangerz era, delivering a hip hop leaning sound and videos that signaled a clear break from her Disney image. Subsequent projects pushed into different lanes, including a psychedelic indie collaboration released for free in 2015, a rock leaning album in 2020, and a glossy pop return with a global hit in 2023 that earned major awards attention.
Britney Spears
Britney Spears first appeared on ‘The Mickey Mouse Club’ in the early 1990s, then launched a record breaking debut with a single and album that topped charts worldwide in 1999. Her early branding leaned on a schoolgirl motif and radio friendly teen pop that defined the turn of the millennium.
By the early 2000s she moved into more provocative performance choices, including a notable 2001 awards show appearance with a live python and a harder edged sound on later releases. A critically praised 2007 album cemented the shift, followed by a multiyear Las Vegas residency from 2013 to 2017 and a bestselling memoir in 2023 that revisited the arc of her career.
Christina Aguilera
Christina Aguilera came up through ‘The Mickey Mouse Club’ and arrived with powerhouse vocals on a 1999 debut album anchored by radio staples that fit the late teen pop wave. Early videos and performances emphasized vocal skill and classic pop styling.
Her 2002 Stripped era intentionally reset that image with harder hitting singles and visuals that embraced an unapologetically adult persona. She followed with a retro soul reinvention on a double album in 2006, then expanded her profile as a coach on ‘The Voice’ while continuing to release music in English and Spanish.
Rihanna
Rihanna opened her career in 2005 with Caribbean inflected pop on back to back albums that introduced her as a fresh faced newcomer. The singles from that period leaned on sunlit themes and dance friendly beats that positioned her as a mainstream radio staple.
A decisive rebrand arrived in 2007 with an album literally titled Good Girl Gone Bad, pairing razor sharp dance pop with darker visuals and a high fashion aesthetic. She kept evolving with moodier records in 2009 and 2010, launched a beauty line in 2017 that reshaped the industry, and headlined the Super Bowl halftime show in 2023 while teasing eventual new music.
Janet Jackson
Janet Jackson started on television with ‘The Jacksons’ in the late 1970s and released two early albums before taking full creative control with Control in 1986. That record and Rhythm Nation 1814 in 1989 combined ironclad choreography with socially minded lyrics and set new standards for pop stagecraft.
In the 1990s she shifted into more overtly sensual territory with the janet. album and boundary pushing videos that defined the era. A Super Bowl halftime show in 2004 became a flashpoint in broadcast culture, after which she continued to tour arenas worldwide and return to the top of the charts with new music and extensive live productions.
Katy Perry
Before pop stardom, Katy Perry recorded a faith based album under her birth name in 2001 and appeared on a series of compilation projects while searching for a mainstream home. Early sessions with producers across Los Angeles helped shape the sound that would soon break through.
Her 2008 debut as Katy Perry arrived with provocative lyrics and glossy power pop hooks that reintroduced her to a global audience. A 2010 album delivered a rare run of five number one singles in the United States, she headlined stadium tours across multiple cycles, and later anchored a theatrical Las Vegas residency from 2021 to 2023.
Demi Lovato
Demi Lovato launched on Disney with the TV movie ‘Camp Rock’ in 2008 and the series ‘Sonny with a Chance’ from 2009 to 2011, pairing acting work with early records that appealed to a young audience. Their first albums blended guitar pop with radio ballads and established a strong touring base.
The shift came with harder hitting singles and a more assertive pop rock sound on releases in 2011 and 2015, followed by a full throttle rock direction in 2022 with a new band and staging. Documentary projects, national anthems, and high profile collaborations rounded out a portfolio that moved well beyond their Disney origins.
Selena Gomez
Selena Gomez headlined ‘Wizards of Waverly Place’ from 2007 to 2012 and fronted a pop band that released three albums by 2011. Early singles and merchandise partnerships reinforced a classic Disney trajectory while she built a filmography of family friendly titles.
She returned with solo albums in 2015 and 2020 that explored more adult themes and R and B textures, then pivoted to prestige television as a lead and executive producer on ‘Only Murders in the Building’ starting in 2021. Beauty and documentary ventures expanded her brand as she balanced acting awards attention with steady chart entries.
Ariana Grande
Ariana Grande broke out on Nickelodeon with ‘Victorious’ from 2010 to 2013 and the spin off ‘Sam & Cat’ from 2013 to 2014, all while training as a vocalist with a strong theater background. Her 2013 debut album leaned toward retro R and B influences and showcased a wide vocal range.
She then transitioned into sleek, adult pop with back to back albums in 2016, 2018, and 2019 that delivered global number ones and festival headlining sets. Screen appearances included a cameo in ‘Don’t Look Up’ in 2021, and she continued to expand into beauty and fashion partnerships alongside arena sized tours.
Vanessa Hudgens
Vanessa Hudgens rose with ‘High School Musical’ beginning in 2006 and toured with the franchise as it exploded in popularity through multiple soundtracks and a theatrical film. Early solo music aligned with pop R and B trends of the time and extended her reach beyond the films.
She pursued darker, independent fare with ‘Spring Breakers’ in 2012 and the drama ‘Gimme Shelter’ in 2013, then balanced that with musical theater and streaming projects. A strong showing in ‘Tick, Tick… Boom!’ in 2021 and a run of holiday films, including ‘The Princess Switch’, demonstrated a comfortable command of both edgy and family friendly spaces.
Bella Thorne
Bella Thorne co led Disney Channel’s ‘Shake It Up’ from 2010 to 2013, pairing sitcom success with teen pop singles and major-brand endorsements. She also wrote a best selling young adult series and built a massive social following during her early career.
After Disney she moved into independent and genre films, including ‘The DUFF’ in 2015, ‘Amityville: The Awakening’ in 2017, and ‘Assassination Nation’ in 2018. She added producing and directing credits, launched multiple lifestyle businesses, and leaned into unfiltered social media that underscored her split from the Disney mold.
Taylor Momsen
Taylor Momsen began acting as a child with ‘How the Grinch Stole Christmas’ in 2000 and later became a central figure on ‘Gossip Girl’ from 2007 to 2011. As the show gained traction she increasingly focused on music and stepped back from regular acting duties.
She formed The Pretty Reckless in 2009 and released a debut album in 2010 that kicked off extensive touring across North America and Europe. Subsequent albums in 2014, 2016, and 2021 delivered multiple rock radio number ones and festival slots that cemented her status as a full time hard rock frontwoman.
Drew Barrymore
Drew Barrymore’s breakthrough came with ‘E.T.’ in 1982, which established her as one of the most recognizable child actors of the decade. She published the memoir Little Girl Lost in 1990 and began to reshape her career with a deliberate selection of projects in the years that followed.
A late 1990s resurgence included ‘The Wedding Singer’ in 1998, ‘Never Been Kissed’ in 1999, and ‘Charlie’s Angels’ in 2000, supported by the production company Flower Films. She maintained a steady slate of films through the 2000s and later expanded into daytime television and lifestyle brands.
Christina Ricci
Christina Ricci grew up on screen with ‘The Addams Family’ in 1991 and ‘Casper’ in 1995, roles that made her a staple of family cinema. By her late teens she began choosing material that challenged expectations and highlighted a dramatic range.
She shifted into adult roles with ‘The Ice Storm’ in 1997 and ‘Buffalo ’66’ in 1998, then delivered acclaimed turns in ‘Monster’ in 2003 and ‘Black Snake Moan’ in 2006. A prominent arc on ‘Yellowjackets’ beginning in 2021 introduced her to a new generation while continuing the pattern of daring choices.
Emma Watson
Emma Watson spent a decade as Hermione Granger in the ‘Harry Potter’ films from 2001 to 2011, growing up on screen while balancing school and international press duties. She used the years immediately after the franchise to broaden her range and explore different corners of the industry.
Her post franchise choices included ‘The Perks of Being a Wallflower’ in 2012 and ‘The Bling Ring’ in 2013, both of which foregrounded adult themes and layered characters. She followed with ‘Beauty and the Beast’ in 2017 and ‘Little Women’ in 2019, plus significant advocacy work and editorial projects.
Kesha
Kesha arrived as a songwriter and guest vocalist before breaking through with a 2009 single that dominated radio and streaming. Her early records leaned into party centric lyrics and electro pop production that made her a fixture of late night TV and festival stages.
She later pivoted toward rootsier instrumentation and autobiographical writing on a 2017 album that earned major award nominations. Releases in 2020 and 2023 blended rock, pop, and country accents and highlighted vocal performances that moved well beyond the neon sheen of her debut era.
Lindsay Lohan
Lindsay Lohan’s early run included ‘The Parent Trap’ in 1998, ‘Freaky Friday’ in 2003, and ‘Mean Girls’ in 2004, which solidified her as a leading teen star. She headlined ‘Herbie: Fully Loaded’ in 2005 and released two pop albums while appearing in studio comedies and dramas.
After periods away from the spotlight she returned to scripted work with the holiday film ‘Falling for Christmas’ in 2022 and followed with ‘Irish Wish’ in 2024. Additional projects, production deals, and entrepreneurial ventures marked a steady reentry into film and television.
Ashley Benson
Ashley Benson appeared on ‘Days of Our Lives’ from 2004 to 2007 before starring on ‘Pretty Little Liars’ from 2010 to 2017. The series became a long running hit that anchored her move from daytime to primetime viewership.
She shifted into edgier cinema with ‘Spring Breakers’ in 2012 and continued with indie projects like ‘Her Smell’ in 2018. Later roles such as ‘The Loneliest Boy in the World’ in 2022 kept her tied to genre and independent films that offered more adult material than her early television work.
Sabrina Carpenter
Sabrina Carpenter co led ‘Girl Meets World’ from 2014 to 2017 and released two early pop albums while touring heavily for a teen audience. Acting credits during this period included television movies and family oriented features.
A turn to mature pop songwriting arrived with releases in 2019 and 2022 that emphasized confessional lyrics and bolder stagecraft. High profile festival sets, late night performances, and global tour dates in the early 2020s showcased a confident adult pop identity that contrasted with her Disney era.
Victoria Justice
Victoria Justice became a Nickelodeon mainstay through ‘Zoey 101’ from 2005 to 2008 and ‘Victorious’ from 2010 to 2013. During those years she also recorded soundtrack features and performed on network tours aimed at younger audiences.
Post Nickelodeon she moved into independent films like ‘The Outcasts’ in 2017 and began releasing solo singles in 2020 that signaled a fresh musical direction. She continued building a filmography with streaming thrillers and romantic comedies while performing at festivals and club venues.
Hilary Duff
Hilary Duff led ‘Lizzie McGuire’ from 2001 to 2004 and starred in films like ‘A Cinderella Story’ in 2004, ‘Cheaper by the Dozen’ in 2003, and ‘The Lizzie McGuire Movie’ in 2003. She also released several pop albums that toured well with teen audiences.
She later took on adult roles with the acclaimed TV dramedy ‘Younger’ from 2015 to 2021 and the sitcom ‘How I Met Your Father’ from 2022 to 2023. Alongside acting she published novels, launched fashion and beauty lines, and built a steady presence as a producer and creative lead.
Share your picks in the comments and tell us which transformations surprised you the most.