After squandering his first Lanois-assisted comeback, 1989’s Oh Mercy, with 1990’s Under The Red Sky, Bob was in a bit of a quandary. In 1991 he released no new album for the first time since the end of his Christian phase a decade prior. When he finally did decide to go back to the studio, he once again fell into the same bad habits that produced Knocked Out Loaded and Down In The Groove. He hired David Bromberg to produce the album, and while those two records had very few self-penned originals, Dylan decided to do a whole album of covers.

The project went well, and everyone seemed happy with the final product, but at the last minute Bob decided to throw on a hastily recorded solo acoustic track, much as he had done with The Wedding Song for Planet Waves or Dark Eyes for Empire Burlesque. So Bob threw a mic up in his garage studio and quickly knocked out 15 or so tracks to choose from. But when he listened back to the tapes, he decided to scrap the Bromberg sessions and just release the acoustic album. While the albums itself didn’t excite anyone particularly, everyone was also relieved that Dylan wasn’t embarrassing himself either. In fact, the only person who really seemed into the album, was Dylan himself; who recorded a nearly identical album of solo acoustic folk songs, World Gone Wrong, the next year. It seemed to keep him happy and busy and re-charge his batteries while waiting for the muse to strike again.

It was a type of album he hadn’t really done since his very first album before he started writing his own material in earnest. While most of Bob’s periods tend to last three or four albums (see the electric trilogy, the born again trilogy, or the Sinatra trilogy), this mid-nineties acoustic folk revival only lasted 2 albums before Bob had gotten everything he would want out of it, buying himself enough time and goodwill to record Time Out Of Mind several years later. So while putting together this playlist, I also included four track from that solo debut (House Of The Risin’ Sun, Fixin’ To Die, In My Time Of Dyin’, and Man Of Constant Sorrow) that fit together in terms of instrumentation and authorship if not chronology. I also included a version of Woody Guthrie’s Pretty Boy Floyd that Bob had recorded for a tribute album in the mid eighties, as there isn’t much between the two periods to really link them together.

Now that Bob knew how to do a record when he didn’t have the songs, he decided never to do that again. A second Lanois-assisted comeback, 1997’s Time Out Of Mind would buy Dylan both the credibility to do what he wanted next time, but also the allowance to take as much time as he needed to get to that next record.