By 2006, however,

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. The ad showed the halo effect of the iPod’s marketing: It helped Dylan win a younger audience, just as the iPod had done for Apple computers. Because of the ad, Dylan’s album was number one on the Billboard chart its first week, topping hot-selling albums by Christina Aguilera and Outkast. It was the first time Dylan had reached the top spot since Desire in 1976, thirty years earlier. Ad Age headlined Apple’s role in propelling Dylan. “The iTunes spot wasn’t just a run-of-the-mill celebrity-endorsement deal in which a big brand signs a big check to tap into the equity of a big star,” it reported. “This one flipped the formula, with the all-powerful Apple brand giving Mr. Dylan access to younger demographics and helping propel his sales to places they hadn’t been since the Ford administration.”