- Cut Song: Bob Johnston, who was producing both men at the time, scheduled a Johnny Cash session in another studio at the Columbia Records Nashville headquarters at the same time Dylan was recording there, and coaxed the two to do some informal duets. "Girl from the North Country" was the only one to make the album. Tapes of some of the other songs surfaced and were heavily bootlegged by Dylan fans until the complete session got an official release on The Bootleg Series Vol. 15 in 2019. The majority of the other songs are versions of Cash classics, with Cash very much leading the session (Dylan seems like he has a bad case of The Knights Who Say "Squee!" in working alongside Cash, and is very tightly wound and nervous). An intriguing performance is Dylan and Cash simultaneously singing "Don't Think Twice, It's All Right" and "Understand Your Man", underscoring the similarity in the two songs (though Cash correctly notes that "We both stole it from the same song," meaning Paul Clayton's "Who's Gonna Buy You Ribbons When I'm Gone?").
- For a long time the Dylan/Cash songs were thought to be the only outtakes from the album, but when an actual Nashville Skyline session tape was offered on eBay in 2008, it included a previously-unknown song that fans called "Goin' to Chicago", a largely-improvised Blues piece. It also got a formal release on The Bootleg Series Vol. 15, but under the title "Western Road". Vol. 15 also features the only-known version of Dylan singing "Wanted Man", a loose rehearsal with Cash to help him learn the song, which he unveiled at his San Quentin concert six days later.
- Development Gag: Dylan's smooth voice is the most noticeable thing on the album, even to the point of people speculating that his motorcycle crash affected his vocal cords in some way. However, people who heard him play Minnesota folk clubs in the 1959-61 era before he went to New York immediately recognized it as the vocal style he'd used back then. One particular bootleg tape recorded by one of his early fans that later went into circulation confirms it, which makes his singing style here Revisiting the Roots.
Trivia / Nashville Skyline