The ad showed the halo

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.

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.”