Steve Jobs

At the end of the listening session, I asked him a well-worn question: the Beatles or the Stones? “If the vault was on fire and I could grab only one set of master tapes, I would grab the Beatles,” he answered. “The hard one would be between the Beatles and Dylan. Somebody else could have replicated the Stones. No one could have been Dylan or the Beatles.” As he was ruminating about how fortunate we were to have all of them when we were growing up, his son, then eighteen, came in the room. “Reed doesn’t understand,” Jobs lamented. Or perhaps he did. He was wearing a Joan Baez T-shirt, with the words “Forever Young” on it.

Bob Dylan

The only time Jobs can ever recall being tongue-tied was in the presence of Bob Dylan. He was playing near Palo Alto in October 2004, and Jobs was recovering from his first cancer surgery. Dylan was not a gregarious man, not a Bono or a Bowie. He was never Jobs’s friend, nor did he care to be. He did, however, invite Jobs to visit him at his hotel before the concert. Jobs recalled:

We sat on the patio outside his room and talked for two hours. I was really nervous, because he was one of my heroes. And I was also afraid that he wouldn’t be really smart anymore, that he’d be a caricature of himself, like happens to a lot of people. But I was delighted. He was as sharp as a tack. He was everything I’d hoped. He was really open and honest. He was just telling me about his life and about writing his songs. He said, “They just came through me, it wasn’t like I was having

to compose them. That doesn’t happen anymore, I just can’t write them that way anymore.” Then he paused and said to me with his raspy voice and little smile, “But I still can sing them.”

The next time Dylan played nearby, he invited Jobs to drop by his tricked-up tour bus just before the concert. When Dylan asked what his favorite song was, Jobs said “One Too Many Mornings.” So Dylan sang it that night. After the concert, as Jobs was walking out the back, the tour bus came by and screeched to a stop. The door flipped open. “So, did you hear my song I sang for you?” Dylan rasped. Then he drove off. When Jobs tells the tale, he does a pretty good impression of Dylan’s voice. “He’s one of my all-time heroes,” Jobs recalled. “My love for him has grown over the years, it’s ripened. I can’t figure out how he did it when he was so young.”

A few months after seeing him in concert, Jobs came up with a grandiose plan. The iTunes Store should offer a digital “boxed set” of every Dylan song every recorded, more than seven hundred in all, for $199. Jobs would be the curator of Dylan for the digital age. But Andy Lack of Sony, which was Dylan’s label, was in no mood to make a deal without some serious concessions regarding iTunes. In addition, Lack felt the price was too low and would cheapen Dylan. “Bob is a national treasure,” said Lack, “and Steve wanted him on iTunes at a price that commoditized him.” It got to the heart of the problems that Lack and other record executives were having with Jobs: He was getting to set the price points, not them. So Lack said no.

“Okay, then I will call Dylan directly,” Jobs said. But it was not the type of thing that Dylan ever dealt with, so it fell to his agent, Jeff Rosen, to sort things out.

“It’s a really bad idea,” Lack told Rosen, showing him the numbers. “Bob is Steve’s hero. He’ll sweeten the deal.” Lack had both a professional and a personal desire to fend Jobs off, even to yank his chain a bit. So he made an offer to Rosen. “I will write you a check for a million dollars tomorrow if you hold off for the time being.” As Lack later explained, it was an advance against future royalties, “one of those accounting things record companies do.” Rosen called back forty-five minutes later and accepted. “Andy worked things out with us and asked us not to do it, which we didn’t,” he recalled. “I think Andy gave us some sort of an advance to hold off doing it.”

By 2006, however, Lack had stepped aside as the CEO of what was by then Sony BMG, and Jobs reopened negotiations. He sent Dylan an iPod with all of his songs on it, and he showed Rosen the type of marketing campaign that Apple could mount. In August he announced a grand deal. It allowed Apple to sell the $199 digital boxed set of all the songs Dylan ever recorded, plus the exclusive right to offer Dylan’s new album, Modern Times, for pre-release orders. “Bob Dylan is one of the most respected poets and musicians of our time, and he is a personal hero of mine,” Jobs said at the announcement. The 773-track set included forty-two rarities, such as a 1961 tape of “Wade in the Water” made in a Minnesota hotel, a 1962 version of “Handsome Molly” from a live concert at the Gaslight Café in Greenwich Village, the truly awesome rendition of “Mr. Tambourine Man” from the 1964 Newport Folk Festival (Jobs’s favorite), and an acoustic version of “Outlaw Blues” from 1965.

As part of the deal, Dylan appeared in a television ad for the iPod, featuring his new album, Modern Times. This was one of the most astonishing cases of flipping the script since Tom Sawyer persuaded his friends to whitewash the fence. In the past, getting celebrities to do an ad required paying them a lot of money. But by 2006 the tables were turned. Major artists wanted to appear in iPod ads; the exposure would guarantee success. James Vincent had predicted this a few years earlier, when Jobs said he had contacts with many musicians and could pay them to appear in ads. “No, things are going to soon change,” Vincent replied. “Apple is a different kind of brand, and it’s cooler than the brand of most artists. We should talk about the opportunity we offer the bands, not pay them.”

Lee Clow recalled that there was actually some resistance among the younger staffers at Apple and the ad agency to using Dylan. “They wondered whether he was still cool enough,” Clow said. Jobs would hear none of that. He was thrilled to have Dylan.

Jobs became obsessed by every detail of the Dylan commercial. Rosen flew to Cupertino so that they could go through the album and pick the song they wanted to use, which ended up being “Someday Baby.” Jobs approved a test video that Clow made using a stand-in for Dylan, which was then shot in Nashville with Dylan himself. But when it came back, Jobs hated it. It wasn’t distinctive enough. He wanted a new style. So Clow hired another director, and Rosen was able to convince Dylan to retape the entire commercial. This time it was done with a gently backlit cowboy-hatted Dylan sitting on a stool, strumming and singing, while a hip woman in a newsboy cap dances with her iPod. Jobs loved it.