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.

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Mick Jagger Tours Solo With Joe Satriani

The Rolling Stones went through a pretty rough patch in the mi-Eighties, but things reached a boiling point when Mick Jagger refused to tour in support of the band's 1986 LP Dirty Work. Instead, he put out a second solo album and launched a brief solo tour to support it in 1988. The setlist was full of Rolling Stones classics, and he hired guitar virtuoso Joe Satriani to play the Keith Richards parts. This was a low blow to Richards and the band nearly broke up as a result, but the following year they put aside their differences and launched the Steel Wheels stadium tour. 

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Robert Plant Refuses to Reunite Led Zeppelin

It was the biggest tease in rock history. For a single night in December of 2007, Robert Plant and the rest of Led Zeppelin did a glorious, smoking two-hour set at London's 02 Arena. Jimmy Page, John Paul Jones, Jason Bonham and most everybody else on the planet was dying for the group to tour. They could have made a ton of cash, but Robert Plant stood his ground and refused to do it. Fans may shake their heads in frustration over the choice, but you have to respect the man for sticking to his guns.

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Van Halen Hire Gary Cherone

Sammy Hagar left Van Halen in 1996, and fans around the world prayed that meant that original singer David Lee Roth was going to return. They appeared with Roth at that year's MTV Video Music Awards, but after a backstage fight they called off the reunion and cut an album with Extreme frontman Gary Cherone. It was a commercial disaster, but the Van Halen brothers would have rather failed on their terms than succeeded with a singer they couldn't stand at that point. In 2004 they toured with Hagar, and in 2007 they folded and did a tour with David Lee Roth. They reportedly kept their distance from each other backstage.

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Radiohead Let Fans Name Their Price

When Radiohead released In Rainbows in 2007, they had a radical pricing scheme: whatever you want. The group set up a website where fans could name their own price, even if that price was zero. They figured that people stole music anyway, so why not let them steal it officially? Many fans did opt to get it for free, but enough others paid that the band made a fortune from the disc. It also helped that they didn't have to give any of the money to a record company, or spend money printing discs. The group insisted the release was a success, but for their next LP in 2011, The King of Limbs, they decided to set price points.

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Green Day Go Broadway

Punk rock and Broadway are at two ends of the musical spectrum, but in 2010 Green Day decided to bridge that gap by turning their 2004 smash LP American Idiot into a Broadway play. It was a pretty big gamble. Broadway productions cost a fortune to mount, and many don't recoup their losses. The reviews were mostly great, but when sales slipped Green Day frontman Billie Joe Armstrong stepped into the leading role. It's scheduled to close on April 24th, but there are plans to bring it on the road – thereby giving hope to punk rock theater nerds everywhere.


Elton John Comes Out Of The Closet

Openly gay singers are commonplace in 2011, but that was not the case back in 1976. (Many even thought that Liberace was straight.) Back then Elton John was just about the biggest rock star in the world, but when he told Rolling Stone that he was bisexual that year, his career began to crater. Letters poured into the magazine calling John a pervert, and many fans refused to continue buying his albums – though things picked up in the early Eighties.

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Jim Morrison Gets Busted For Obscenity

Nobody disputes that Jim Morrison was drunk and taunting police officers from the stage at a Miami concert in 1969, but his arrest and charge for indecent exposure was almost undoubtedly trumped up. Nevertheless, the incident caused other promoters to balk at hiring The Doors, and they went into a vicious downward spiral. Much of this could have been averted if Morrison had admitted to the act and hammered out a plea, but he refused to back down. In December 2010 outgoing Florida Governor Charlie Crist issued a posthumous pardon to Morrison.

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David Bowie Performs After Nine Inch Nails, Playing No Hits

In 1990 David Bowie went on a tour that he claimed would be the last opportunity for fans to hear his vast catalog of hits. Five years later he hit the road with Nine Inch Nails. It was a high point in the band's career and a low point for Bowie, yet Trent Reznor insisted that Bowie close the show out each night. Towards the end of NIN's set Bowie came onstage to sing with the band, slowly transitioning into his own set. The trick didn't stop thousands of fans from walking out when Reznor left the stage, and those that stayed didn't hear a single famous Bowie song. He played mainly new songs with a smattering of obscure oldies, like "Andy Warhol" and "Teenage Wildlife." Night after night he walked onto that stage and refused to appease the crowd with "Ziggy Stardust" or "Rebel Rebel." When he hit the road in 1999, however, the hits came back.

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Pearl Jam Stops Making Videos, Refuses To Work With Ticketmaster

Pearl Jam's 1991 debut Ten transformed the band into one of the biggest bands in the world, largely fueled by MTV playing their videos for "Jeremy" and "Even Flow" around the clock. When it came time for the follow-up LP Vs. the band decided to downscale the band's ambitions, beginning by refusing to make music videos. The album still sold by the millions, but by 1994 they took an even harder stance by refusing to perform in Ticketmaster venues. Both decisions made reaching a massive audience difficult, and they began selling fewer and fewer records.  But their fanbase remained incredibly loyal and they continue to pack every venue they play – though they have long since reversed both decisions.

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Sinead O’Connor Tears Up A Photo Of The Pope On Live TV

Talk about a ballsy move. In October 1992 Irish singer Sinead O'Connor was pissed off about child abuse scandals within the Catholic Church, so she decided to use her platform on Saturday Night Live to make a point. Without telling producers in advance, she tore a photo of the Pope in half after a performance of Bob Marley's "War." This is long before the public was aware of the Catholic Church's role in covering up child abuse, and the incident ignited a firestorm. To this day O'Connor says that she has no regrets, but it definitely dealt a near-lethal blow to her career.



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.

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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.

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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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