The Traveling Wilburys album that made Bob Dylan uncomfortable

It felt like a strange rock and roll miracle when the Traveling Wilburys first got together.

No one could have scripted a better supergroup to come together, but since all of them were friends, it was easier for them to hang out and strum their guitars until the early hours of the morning than worry about what their career was going to be. The whole thing was done as a bit of fun, but that didn’t mean that everyone had to be completely comfortable when they first walked into the room.

Granted, is there anyone who wouldn’t be intimidated by being in a band that had George Harrison and Bob Dylan in the mix? Each of them were living legends in their own right, and since the goal of every Wilburys record was to have every single band member chip in, it would have been impossible for anyone to even dare to make a suggestion for how one of Dylan’s lyrics should sound or suggest that Roy Orbison try another take when working on his classic lead vocal lines.

But with Harrison at the helm, it was a lot more laid-back than anyone could have imagined. His goal with the band was to have a group that he could hang out with rather than a bunch of hired guns, but he liked to surround himself with people who excelled in their craft as well. Tom Petty already had mastered heartland rock by the time he started working with the band, but for all of the talent on display, Dylan was the one who was the most hesitant about working with a group all over again.

His work with Petty on his comeback tours in the 1980s may have been fun, but outside of them and The Band, Dylan was never the kind to be a group member most of the time. Robbie Robertson wasn’t going to be telling Dylan that he thought a song should be played a certain way, so if he decided to come in as an equal, that meant leaving his ego at the door and trying to blend in as another band member.

That mentality was what helped free Harrison from the shadow of The Beatles, but Dylan wasn’t quite sure if the whole thing was going to work. He had already booked a tour when the band decided to make an album’s worth of tunes, and while his tunes like ‘Tweeter and the Monkey Man’ and ‘Dirty World’ are among the album’s highlights, Harrison remembered how stressed Dylan was working alongside his friends.

He was more than happy to watch Orbison sing, but Harrison knew Dylan would be much more comfortable once the band had settled in on the second record, saying, “I think everyone, particularly Bob, was more willing to do it this time. Never having been in a band before, Bob wasn’t quite sure what the result would be on the first one. This time, we knew what to expect. Bob was keen to do this one.”

Then again, that kind of camaraderie probably came from everyone wanting to make one more album for Orbison. The crooner never got to see the massive success that the band would become after he passed away, but since the band was steadily going up the charts, Dylan was willing to step up on the next record. He probably wasn’t everyone’s first choice for a singer, but tunes like ‘If You Belonged To Me’ and ‘Inside Out’ benefit a lot from his gruffer voice on the record.

It may have taken a while for Dylan to open up, but it’s not like Harrison hadn’t encountered this side of him before. He had already asked to be let into his heart all the way back in the 1970s with ‘I’d Have You Anytime’, and this was simply his way of breaking down that rough exterior among his other friends.

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