Britney Spears

A product of the Mickey Mouse Club, Britney Spears shot to hyperstardom in the 90s. Initially loved but then ridiculed for her babyish voice and provocative image, Spears has been reevaluated by avant garde stars like Rina Sawayama, saying “I still feel that same excitement when I listen to songs from back then that inspired me.”

Whitney Houston

A powerhouse of the music world, Whitney Houston wasn’t always a legendary musician. In fact, being a high-profile black singer in the 80s and 90s was a struggle. Said Houston, “Sometimes it gets down to ‘You’re not black enough for them. You’re not R&B enough. You’re very pop.” Activist the Reverend Al Sharpton even took to calling her ‘Whitey’ Houston.

Sinéad O’Connor

Known as much for her searing vocals as for her volatility on stage (which peaked with her tearing apart a picture of Pope John Paul II on Saturday Night Live), Sinéad O’Connor was long dismissed as a one-hit wonder, whose teary rendition of the Prince-penned Nothing Compares 2 U was much-mocked. However, few have matched her singularly powerful voice.

Björk

Icelandic singer-songwriter-actress Björk is famously as avant garde as they come, but remains one of the world’s best-loved artists. Still, 1993’s Debut landed with a thud in the US. Rolling Stone decried a “phalanx of cheap electronic gimmickry” and Musician criticised the “odd assortment of growls, moans and chirps she relies upon.”

Carly Rae Jepsen

The reality TV pop pipeline has had mixed results. For every Kelly Clarkson and Jordin Sparks there’s a Kree Harrison, Skylar Laine and Harmon Tryst. And that last one was made-up. So you’d be forgiven for thinking that third-placed Canadian Idol contestant Carly Rae Jepsen was destined for obscurity. 18 million records later, who’s laughing now?

Amy Winehouse

Amy Winehouse, who died in 2011 aged just 27, was hounded by the press in for her substance issues. Two years before her death, American journalist Robert Christgau lambasted the British singer-songwriter as “a self-aggrandizing self-abuser who’s taken seriously because she makes a show of soul.” But in 2017, Bob Dylan called Winehouse “the last real individualist around,” which carries much more weight.

Cyndi Lauper

Fingered as “haystack-haired” and “goofy” by the Chicago Tribune in 1986, it’s fair to say that the early days of Cyndi Lauper were greeted with rapturous popularity but little critical credence. It was only decades later that the Girls Just Want To Have Fun singer was reappraised as a sanguine feminist who effectively white-outed Robert Hazard’s original track from music history.

Nina Simone

Credit: David Redfern via Getty Images

An undoubted music legend, Nina Simone struggled with mental health issues and was often portrayed as vicious and paranoid throughout her career. But when it was revealed that the US government was in fact spying on her and manipulating her to political ends, Simone suddenly seemed a lot less delusional.

Dolly Parton

Dolly Parton, who infamously quipped that “it costs me a lot of money to look this cheap,” is one of the most successful singer-songwriters ever. However, she started out as the largely ignored duettist of country musician Porter Wagoner. When Parton was noticed, it was for the wrong reasons, as at first Wagoner’s audiences angrily demanded the return of his former partner, Norma Jean Beasler.

Katy Perry

With record sales of over 143 million, you’d be forgiven for thinking Katy Perry’s superstardom was always a sure thing. In reality, her debut was a panned gospel album released under her birth name, Katy Hudson. Producer Tommy Collier says few believed she’d succeed, telling E! Magazine, “They just didn’t get it. I was like, ‘Dude, that girl’s probably going to be a big star.'”