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In 1990, Bob Dylan released Under the Red Sky, one of his worst-reviewed albums. It is one of the few albums in Dylan’s discography that features many other musicians, including George Harrison, Elton John, and David Crosby. Dylan himself admitted that the album wasn’t his best work. He said he felt disillusioned while recording it. He said that his work with The Traveling Wilburys made it difficult for him to focus on his solo project.

Bob Dylan sings into a microphone and wears a bow tie.
Bob Dylan | Jeffrey R. Staab/CBS via Getty Images

Bob Dylan released the album ‘Under the Red Sky’ in 1990

In 1990, Dylan released Under the Red Sky, his follow-up to 1989’s Oh Mercy. Fans widely regarded Oh Mercy as a comeback for Dylan, so Under the Red Sky came as a disappointment. He seemed disenchanted with the album before he even finished recording it.

“You know there was a weariness about him that actually made me feel so much more for him,” producer David Was said, per the book Down the Highway by Howard Sounes. “There were times when he looked absolutely beleaguered, doing this stuff. It occurred to me that it was a continuous burden having to be ‘Bob Dylan’ after all these years.”

The album received negative reviews. It also sold so poorly that Dylan reportedly did not want to release another album for seven years.

Bob Dylan said the album was a challenge

Looking back, Dylan agreed that Under the Red Sky was not one of his best albums. He explained that working on that album at the same time as The Traveling Wilbury’s Volume 3 was too much.

“I made this record, Under the Red Sky, with Don Was, but at the same time I was also doing the Wilburys record,” he told Rolling Stone in 2006, adding, “I don’t know how it happened that I got into both albums at the same time. I worked with George [Harrison] and Jeff [Lynne] during the day — everything had to be done in one day, the track and the song had to be written in one day, and then I’d go down and see Don Was, and I felt like I was walking into a wall.”

He said that working with The Traveling Wilburys sapped him of his creative energy for his solo album.

“[Was would] have a different band for me to play with every day, a lot of all-Stars, for no particular purpose,” he said. “Back then I wasn’t bringing anything at all into the studio, I was completely disillusioned. I’d let someone else take control of it all and just come up with lyrics to the melody of the song. He’d say, ‘What do you want to cut?’ – well, I wouldn’t have anything to cut, but I’d be so beat down from being up with the Wilburys that I’d just come up with some track, and everybody would fall in behind that track, oh, my God.”

His challenges with ‘Under the Red Sky’ come through to the listener

Dylan said that his slumping creativity was damaging to both projects.

“Both projects suffered some,” he said. “Too many people in the room, too many musicians, too many egos, ego-driven musicians that just wanted to play their thing, and it definitely wasn’t my cup of tea, but that’s the record I’m going to feature.”

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Dylan had recently hit a career low while on tour with Tom Petty and the Heartbreakers, so this was not the time to overstretch himself creatively. He needed time to rebuild as an artist after his creative low point. Instead, he put himself far out of his comfort zone by collaborating with a large number of other musicians. Unfortunately, this comes through to the listener.

Of course, The Traveling Wilburys were not responsible for the performance of Under the Red Sky, but it likely would have been better if Dylan had worked on them at separate times.