25 Boldest Career Moves in Rock History: Bob Dylan, Britney Spears - Rolling Stone
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The 25 Boldest Career Moves in Rock History

From Bob Dylan becoming born again to Panic! at the Disco dropping the exclamation mark, the decisions that have changed the music world

From the very beginning of rock & roll musicians have made shocking career moves – from marrying their cousins to shaving their heads in front of hundreds of flashing cameras. Here’s a look at the 25 boldest ones of all time.



Britney Spears Shaves Her Head

Few celebrities have suffered as public a breakdown as what Britney Spears went through in early 2007. That February, the pop icon left a Antigua drug rehab center after just one day of treatment and returned to Los Angeles, while being followed by an army of paparazzi. In what's become one of the most stunning moments in her career, she headed into a hair salon and shaved her head with clippers. The images were beamed around the world. For a woman whose career was built upon her looks, it was the boldest of bold moves.

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Lauryn Hill Releases Unplugged 2.0

Much like George Michael, Lauryn Hill did not enjoy her transformation into a superstar. Her 1998 debut The Miseducation of Lauryn Hill was one of the most acclaimed albums of the Nineties, but she has yet to create a follow-up. The closest thing was her 2002  Unplugged LP. Many of the songs were little more than rough sketches and she was just learning how to play guitar when it was taped -  but her label was desperate for material and it was released. This was not the disc that her fans were craving and it quickly fell of the charts and was forgotten.

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George Michael Walks Away From His Career

It's easy to forget now, but in the late Eighties George Michael was one of the biggest rock stars in the world. Everything he touched turned to gold, but he got pissed at Sony in 1991 when he felt they didn't adequately support his new LP Listen Without Prejudice Vol. 1. His response was to completely walk away from his career for the next five years. The industry went through a series of radical changes during his absence, and when he came back with Older in 1996 his audience had largely moved on. He made his point, but it was costly.

Tasos Katopodis/Getty Images for BWR Public Relations)


Chris Cornell Works With Timbaland

Around 2008, Interscope chief Jimmy Iovine had one solution to all problems: "Bring in Timbaland." Weezer mocked him for it in their hit "Pork and Beans," but Chris Cornell was foolish enough to listen. By that point Soundgarden was long dead and Audioslave had turned back into Rage Against the Machine. The result was the audio equivalent of a chocolate-covered cheeseburger: People enjoy the elements separately, but together it just makes you want to vomit. Cornell got the message, and the next year he was screaming out "Spoonman" onstage at Lollapalooza with a reformed Soundgarden. The universe was back in order.


Lil Wayne Makes a Rock Album

Lil Wayne was the biggest rapper in the world in 2008 when he decided to make a rock record. Early buzz on the disc was horrendous and it got delayed over and over, finally seeing the light of day in February 2010. Critics tore Rebirth to shreds and Wayne took the message to heart, returning to rap on his next release. It was like Michael Jordan playing baseball – which was also a terrible idea.

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Bruce Springsteen Fires the E Street Band

By 1989 Bruce Springsteen was getting creatively restless. He had been playing with The E Street Band for 17 years, and was beginning to feel creatively boxed in. On a 1988 Amnesty International tour with Sting he noticed how free the artist felt without The Police. The next year he phoned up every member of the E Street Band and told them it was over. He then released two albums on the same day (Human Touch and Lucky Town) that he cut with studio musicians.  They were met with the worst reviews of his career. "I tried writing happy songs in the early Nineties," Springsteen said in his 1999 Rock and Roll Hall of Fame induction speech. "It didn't work; the public didn't like it." That same year he hit the road with the reunited E Street Band.

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Prince Changes his Name to an Unpronounceable Symbol

In 1993, Prince was fed up with his label, Warner Bros. They wanted him to release fewer CDs so he wouldn't flood the market and they could better promote him. He couldn't get out of his contract, but he could change his name to an unpronounceable symbol, largely to mess with them. Journalists started to call him "the artist formerly known as Prince," but in 2000 he went back to Prince when his Warner contract expired. During that time, sales of his new music slowed down significantly, but he still managed to get his point across.


Garth Brooks Transforms Into Chris Gaines

Garth Brooks sold more albums than any other artist from the Nineties, but he was bored by the end of the decade and decided to do something radical: he created a musical alter-ego named Chris Gaines. This new persona sang pop music and had a whole fabricated backstory that Brooks planned on turning into a movie called The Lamb. Unfortunately, fans hated everything about Gaines and the whole thing dealt an incredible blow to Brooks' career.

Luciano Viti/Getty


Neil Young Goes New Wave

Neil Young spent the first 15 years of his career building a loyal audience of rock fans. Then he devoted most of the Eighties to alienating them with a series of eclectic, genre-based albums. It started with the release of his 1982 LP Trans. For people raised on "Heart of Gold" and "Old Man," it was quite jarring to see Young in a skinny tie singing "Computer Age" into a vocoder made his lyrics unintelligible. It sounded like Kraftwerk, not Crazy Horse. The disc has developed a following over the years, but at the time most people just found it baffling. Label chief David Geffen was so upset he sued Young for creating "unrepresentative work."

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Bob Dylan Gets Born Again

On 1965's "Subterranean Homesick Blues" Bob Dylan sang "Don't follow leaders, watch your parking meters" – but in 1979 Dylan started singing a different tune when he became a born-again Christian.  He hit the road performing nothing but new gospel songs from his LP Slow Train Coming, often to incredibly hostile crowds. Here's some sample stage dialogue: "I told you 'The Times They Are A-Changing' and they did! I said the answer was 'Blowin’ In The Wind' and it was! And I'm saying to you now, Jesus is coming back, and he is! There is no other way to salvation."

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