As part of the deal, Dylan appeared in a television ad for the iPod, featuring his new album,
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
Among Jobs’s prized CDs was a bootleg that contained a dozen or so taped sessions of the Beatles revising “Strawberry Fields Forever.” It became the musical score to his philosophy of how to perfect a product. Andy Hertzfeld had found the CD and made a copy of it for Jobs in 1986, though Jobs sometimes told folks that it had come from Yoko Ono. Sitting in the living room of his Palo Alto home one day, Jobs rummaged around in some glass-enclosed bookcases to find it, then put it on while describing what it had taught him:
It’s a complex song, and it’s fascinating to watch the creative process as they went back and forth and finally created it over a few months. Lennon was always my favorite Beatle. [He laughs as Lennon stops during the first take and makes the band go back and revise a chord.] Did you hear that little detour they took? It didn’t work, so they went back and started from where they were. It’s so raw in this version. It actually makes them sound like mere mortals. You could actually imagine other people doing this, up to this version. Maybe not writing and conceiving it, but certainly playing it. Yet they just didn’t stop. They were such perfectionists they kept it going and going. This made a big impression on me when I was in my thirties. You could just tell how much they worked at this.
They did a bundle of work between each of these recordings. They kept sending it back to make it closer to perfect. [As he listens to the third take, he points out how the instrumentation has gotten more complex.] The way we build stuff at Apple is often this way. Even the number of models we’d make of a new notebook or iPod. We would start off with a version and then begin refining and refining, doing detailed models of the design, or the buttons, or how a function operates. It’s a lot of work, but in the end it just gets better, and soon it’s like, “Wow, how did they do that?!? Where are the screws?”
It was thus understandable that Jobs was driven to distraction by the fact that the Beatles were not on iTunes.