Bob Dylan fans will forever argue about the precise moment when his career hit rock bottom, but most pin it somewhere around the time that Down in the Groove landed with a thud in record stores in May 1988. Columbia executives held up its release for a full year after he turned it in, and critics ripped the bizarre collection of mostly cover tunes to shreds. "I was what they called over the hill," he wrote in Chronicles. "The mirror had swung around and I could see the future – an old actor fumbling around in garbage cans outside the theater of past triumphs."
Dylan had barely any new material, so he set out to make a Self Portrait–style covers album. The recording process was bizarre even for Dylan: He used a different band for each session – one had Steve Jones of the Sex Pistols and Paul Simonon of the Clash; another deployed Jerry Garcia, Bob Weir and Brent Mydland of the Grateful Dead, who were on hand as Dylan tackled two songs by Dead lyricist Robert Hunter that the band had rejected.
"It was quite difficult," Simonon says. "We'd do three songs, and by the third I'd just about remember how the songs went before we started recording them. But instead of recording them, we went on with another three songs, and then another three songs, and then another three songs."
After time on the road with the Dead and Tom Petty in
1987, a couple of subpar Dylan originals (one new, one an Infidels outtake)
were tacked on to the covers, which eventually included Wilbert Harrison's "Let's
Stick Together" and Arthur Alexander's "Sally Sue Brown." It
seemed Dylan was headed for the artistic abyss. But soon he kicked off his
Never Ending Tour and began an epic rebirth.