5 Singer Reinventions That Worked & 5 That Made No Sense

5 Singer Reinventions That Worked & 5 That Confused Everyone

Welcome to MsMojo, and today we’re breaking down the most notable times that musicians tried (and failed) to pull off a public image 180.

#5: Lil Wayne

Confused Everyone

To this day, it's hard to know exactly what Dwayne “Lil Wayne” Carter was thinking when it came to his notorious 2010 album “Rebirth.” Hot off the heels of his critically acclaimed, Grammy winning, and best selling 2008 record “Tha Carter III,” Wayne announced in 2009 that he was leaving hip hop behind. After a series of delays, “Rebirth” finally dropped in February of 2010… and it was met with an icy reception. It appeared that Wayne's vision of rock ‘n’ roll was drenched with Auto-Tune and borrowed more from Blink-182 than Led Zeppelin. “Rebirth” was almost unanimously described by critics as the worst album of 2010, and caused Wayne to quietly abandon his rock star dreams.

#5: Pink

Worked

When Pink first hit the scene in 2000, she was marketed as an R&B singer… despite the fact that she never wanted to be one. Her debut album, “Can't Take Me Home” was radio-ready but creatively stifling, built more on LaFace Records’ vision than her own. So for her follow-up, Pink took a hard left: teaming up with 4 Non Blondes’ Linda Perry, she leaned into pop-rock confessionalism, ditched the glossy production, and finally took control of her narrative. The result was “Missundaztood,” a deeply personal, genre-blurring smash that sold over 13 million copies worldwide and made Pink a household name.

#4: Garth Brooks

Confused Everyone

Possibly the radical case of a musician attempting a total reinvention, Brooks’ bizarre transformation into the fictional Chris Gaines will be studied for generations. Country singer Brooks developed the Gaines alter ego as both a marketing stunt and as a way to explore new sounds, donning goth-inspired wigs and makeup in the process. Brooks’ sole album as Gaines, fittingly entitled “Garth Brooks in...the Life of Chris Gaines,” gave him his first top 40 hit on the Billboard Hot 100: the tender R&B ballad “Lost in You.” But it ultimately failed to perform and has mostly been forgotten outside of its novelty.

#4: Taylor Swift

Worked

By the time “1989” rolled around, Taylor Swift had already dipped a toe into pop with 2012’s “Red”. But it was still straddling the line, with enough acoustic flourishes and emotional balladry to keep country radio on board. “1989,” then, was the clean break. She chopped the curls, moved to New York, and teamed up with Swedish pop virtuoso Max Martin to deliver a slick, synth-heavy album that owed more to “True Blue” era Madonna than anything coming out of Nashville. With colossal hits like “Shake It Off” and “Blank Space,” Swift proved she wasn’t just crossing over; she was taking over. The country girl was gone, and in her place stood the blueprint for 2010s pop.

#3: Snoop Dogg

Confused Everyone

You'd be hard-pressed to find someone who doesn’t know Snoop Dogg. Whether it’s hanging with Martha Stewart, or his eclectic social media presence, Snoop has seemingly done it all. So, it only tracks that, after years as a legendary and prolific rapper, he would naturally make the transition to… performing reggae? Rebranding himself to Snoop Lion in 2013, the artist traveled to Jamaica and immersed himself in its culture, taking inspiration from famous reggae musicians like Bob Marley, Peter Tosh, and Bunny Wailer. Unfortunately, Snoop’s leap of faith went up in smoke: the resulting Reincarnated album received lukewarm reviews at best, and peaked at #16 on the Billboard 200 chart.

#3: Madonna

Worked

By the late ’90s, Madonna’s once-untouchable pop reign had started to wobble — her tabloid antics were outpacing her chart performance, and the club-ready sound that made her an ’80s icon was starting to go stale. Enter “Ray of Light.” Teaming up with producer William Orbit, she traded neon synthpop for ambient electronica, trip-hop, and spiritual introspection. The result was a bold, future-facing reinvention that embraced motherhood, mysticism, and millennium anxieties in equal measure. Critics hailed it as her artistic rebirth, while fans were just relieved that Madonna still had surprises left in her.

#2: Prince

Confused Everyone

Only Prince could declare war on his record label by changing his name to a symbol no one could pronounce—and somehow still make it feel poetic. In 1993, fed up with Warner Bros.' control over his music and release schedule, he rebranded himself as the “Love Symbol”: a hybrid of the male and female signs meant to represent freedom and artistic purity. Unfortunately, what he saw as liberation, the public mostly saw as a head-scratcher. Media outlets resorted to calling him “The Artist Formerly Known as Prince,” and casual fans struggled to follow the message behind the mystique. Still, for all the eye-rolling headlines, the music didn’t falter—albums like “The Gold Experience” and “Emancipation” proved he was still operating miles ahead of the curve, even if no one quite knew what to call him.

#2: Bob Dylan

Worked

By 1965, Bob Dylan had been reluctantly saddled with the title of “Spokesman of a Generation” — a role he never asked for and actively resisted. So he did what any self-respecting iconoclast would do: he blew it all up. Dylan went electric with the game-changing 1965 album “Bringing It All Back Home,”, ditching acoustic folk for a raucous new sound that blended rock instrumentation with dreamy, often cryptic lyrics. Folk purists weren’t amused: his plugged-in set at that year’s Newport Folk Festival drew boos and backlash. But Dylan wasn’t interested in pleasing anyone, only in moving forward. It was a bold reinvention that baffled many at the time, even if history has long since vindicated him.

#1: Miley Cyrus

Confused Everyone

It would be an understatement to say that Cyrus’ 2013 album “Bangerz” represented a major turning point in the former Disney kid’s career. Seeking a change from her lead role on “Hannah Montana,” Cyrus drastically overcorrected, embracing a more mature, more adult image, but without giving fans time to adjust to the changes she was making. Her performance with R&B star Robin Thicke at the 2013 MTV Video Music Awards has since become the stuff of pop culture legend… and not in a good way. It should be noted, though, that in the years since, Cyrus has pulled off a massively successful career comeback, and her recent records more than reflect that.

#1: David Bowie

Worked

Before 1972, David Bowie was a clever, if inconsistent, art-pop oddity. Then came “The Rise and Fall of Ziggy Stardust and the Spiders from Mars,” a glam-rock concept album that introduced the world to Ziggy, a bisexual alien rock star sent to save Earth. It was theatrical, bizarre, and completely unlike anything else at the time. At first, audiences didn’t know what to make of the lipstick, jumpsuits, and cosmic mythology. But Bowie committed so fully to the character that confusion gave way to obsession. Ziggy wasn’t just a persona: he was a portal. The reinvention worked so well that it nearly consumed Bowie himself, but it also turned him into a legend, setting the gold standard for pop shapeshifting.

Which singer reinvention on our list shocked you the most? Be sure to let us know in the comments below!