In 1990, Rolling Stone assembled a series of special issues dedicated to the "Four Decades of Rock." For the Eighties Issue — which included massive stars such as Michael Jackson and Madonna — Bruce Springsteen was chosen for the cover. 

"He had a very specific idea for that cover," says Annie Leibovitz. "He wanted to use the American flag. We located a couple of large ones and hung them up in my first studio in New York, on Eighteenth Street, and photographed him against them."

"I was very conscious of being an American musician and addressing the issues of the day," says Springsteen. "There was a sense that the flag was up for grabs, that you had the right in staking out your claim to its meaning and to the kind of country you wanted your kids to grow up in."

"We tried a lot of different things," says Leibovitz. "I even asked Keith Haring to paint a flag on the wall of a building across the street" — an image that eventually made it into the packaging for Springsteen's 1995 Greatest Hits album. The cover eventually chosen for Rolling Stone wasn't Leibovitz's favorite shot. It was an outtake from Leibovitz's shoot for the cover of Springsteen's 1984 smash, Born in the U.S.A. — for which he picked the now-famous picture of him taken from the back, a cap in his pocket.

"I'm still not convinced [he chose the right photo for the issue]," says Leibovitz. "He famously doesn't pick the most attractive picture of himself. He's not interested in how he looks."

Still, Springsteen was so sufficiently aware of his appearance that at the shoot he unveiled a new, more chiseled physique — a far cry from the scraggly, street-rat look he'd cultivated previously. "I started exercising because I'd reached thirty-two, and I couldn't eat the way I used to," says Springsteen. "I realized that I could get out of shape — and that was bad for my job description!"

Springsteen is modest but proud about his selection to represent the Eighties. "It easily could have been Michael Jackson or Prince or Madonna," he says."But using me, well, I suppose that's what I was aiming at. I was very aware that the people I was referencing were people who were not afraid to take on some history as part of their song and dance. I worked through [the Eighties] to find my link in the chain of artists who were willing to do that — whether it was Woody Guthrie or Bob Dylan or Elvis or James Brown, Curtis Mayfield, Marvin Gaye. That was the kind of impact I was interested in having." The story that accompanied the cover reflected Springsteen's sense of his place in history. "In the midst of a confusing and complex decade," wrote the piece's author, Mikal Gilmore, "he wrote more honestly, more intelligently and more compassionately about America than any other writer of the decade."

"I wanted to write music that was charting the ever-changing distance between American ideals and American truths," Springsteen told Gilmore, "to explore what was happening in the middle, to be a creative voice in that discussion."

This story is from the May 18, 2006 issue of Rolling Stone.

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