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.