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The songs Jerry Garcia said only Bob Dylan could sing: “The combination of the beauty and the bitterness”

Fri 16 January 2026 22:00, UK

You might think you’re a big fan of Bob Dylan, but no matter how deep your love for the folk legend goes, there’s one person who will always seemingly be placed as his number one fan.

Step forward Jerry Garcia, a man who was not simply a fan of Dylan’s work, but a complete devotee to his contributions to the world of music. Always looking for a way to praise one of his musical contemporaries and heroes, there’s little doubt that if you were to ask Garcia for his thoughts on Dylan, he’d be able to chew your ear off for hours.

Over the course of the Grateful Dead’s existence, the band would perform many of Dylan’s songs both on record and in a live capacity, and while many artists have chosen to give their own interpretations on songs he originally wrote, there’s a case to be made that Garcia and his band were responsible for some of the most faithful renditions of his work.

Not only was Garcia a huge fan of Dylan’s but the feeling was mutual, and despite there being a handful of sonic differences between their respective sounds, Dylan was able to recognise that there was a strong connection between their approaches, being closely aligned as a result of being part of the same counterculture movement and writing politically-motivated protest songs.

There are, of course, so many reasons to love Dylan and his work, but very few have ever been able to match him or his prolific output – not even the Grateful Dead can claim to have put out a fraction of the amount of studio records that Dylan has produced over the years. Not only this, but Dylan’s songwriting across all of these releases has remained exemplary, and few are able to reach the same high standard of songwriting.

Garcia was all too aware of this, and despite having tried to perform some of his work, he knew that there were a handful of songs that only Dylan himself was capable of producing and performing. During a 1981 interview with Blair Jackson and David Gans, Garcia expressed this feeling about the songs he believed were among Dylan’s masterpieces, especially from a lyrical point of view.

“‘Positively 4th Street’ has this way of doing it where it’s beautiful,” he argued, “And ‘It’s All Over Now, Baby Blue’ is basically a putdown, too. It’s one of those things like, ‘you’re losing bad – dig yourself’. Being able to say that and say it beautifully.”

He continued by saying how Dylan was one of the first people to turn him on to the power of words in songs. “It was the beautiful sound of ‘Positively 4th Street’ that got to me more than the bitterness of the lyric,” Garcia added. “The combination of the beauty and the bitterness, to me, is wonderful. It’s like a combination of something being funny and horrible; it’s a great combination of two odd ingredients in the human experience. Anybody who can pull it off that successfully is really a score. That’s something that only Dylan has been able to pull off, in terms of modern songwriting.”

Dylan’s unmatched songwriting remains powerful to this day, and while many have tried to emulate his expertise over the years, few have been able to recognise this brilliance and respectfully sat back to enjoy it in the way Garcia did, and this was a lifelong admiration he took with him to his grave.