I’m just working this one out video by video, so play along.
In 1935, Sleepy John Estes recorded a song, “Someday Baby Blues”. This is a fairly typical country blues song, with Estes demonstrating his “crying” style. According to Wikipedia, Estes sounded so convincingly like an old man (he was only thirty-six when he recorded this, that by the 1960s many blues music hunters assumed that he was long dead, but he was tracked down, living in poverty, and was able to tour again. Dylan mentions Estes in the liner notes for Bringin’ It All Back Home. Here he is:
In 1941, Big Maceo Merriweather recorded the song as a Chicago blues song as “Worried Life Blues”. It was his biggest hit, and was widely covered. Here is that:
In 1955, Muddy Waters recorded the song, with Jimmy Rogers on guitar. The song was a hit the following year, when Dylan was fourteen years old and listening to the radio a lot. Here’s the Muddy Waters version, which he titled “Trouble No More”:
Just for kicks, let’s note that the Allman Brothers covered the Muddy Waters version and electrified it all up in 1969. Here’s a later live version:
Which brings us to 2006. That year, Bob Dylan released his thirty-second studio album, Modern Times. From that he released a single, “Someday Baby”, taking the title back towards the Estes version but carrying a lot of the Chicago blues sound with it. That song in turn won the Grammy for Best Rock Vocal Performance in 2007 (Dylan did not attend that ceremony, so there won’t be a blog entry for it). So here’s that song:
Ok, so finally the album itself needed to be promoted. And Dylan, being the type of non-sell out sell-out that he is, licensed it to Apple, who used it to help them sell iPods when those were a thing that people bought:
So, to sell an iPod, Dylan had to channel Sleepy John Estes through Muddy Waters and the Allman Brothers. It’s a lot of weight to carry for an ad for an outdated technology.