Bob Dylan, Grateful Dead and why Stella Blue keeps making its way into his setlist

A long-standing connection with The Grateful Dead classic, Bob Dylan has outed Stella Blue more than a few times in recent shows. Rough and Rowdy Ways has offered him chance after chance to showcase the Wake of the Flood piece, and who would not want to hear such a classic rattled out by the great man himself? His intimate tours with The Grateful Dead are no more, and to some degree, his continuous playing of Stella Blue is a way of keeping the band and its members who are no longer with us, alive on stage. The Grateful Dead were a prolific band defined by their presence on stage and their longevity in touring. A close camaraderie with Dylan is perhaps unexpected, but there is something about these recent performances which rings a little sentimental. 

Dylan has played Stella Blue live from 2023 to 2024, twenty-two times. He has played the song almost as many times as The Grateful Dead tribute band, Joe Russo’s Almost Dead. Just two more, Dylan. Give us a slice of the good stuff in Nottingham. He likely will, and given the certainty of it on the Outlaw Music Festival setlist, it seems to be a constant point for the show. Perhaps this is as close as Dylan gets to playing with those no longer kicking around. It is no secret The Grateful Dead is on its last legs, with most members sadly passed or having no interest in touring again. We can keep the spirit of legends alive by playing them on stage. It is why Van Morrison is enlisting his vocal charms on cover albums – albeit of brutally poor quality. 

Did Dylan try and join The Grateful Dead? Few claim he did but his desire to join was rebuffed by Garcia. It occurred a few short years after Dylan and the Dead, a miserable live album. A low point for all artists involved. Decades on and the exoneration is ongoing, the performances of Stella Blue ever stronger under Dylan, who seems to have caught a groove for playing it live. His adaptation of classic tracks into the blues-like style of the Rough and Rowdy Ways tour has been an incredible opportunity to revisit why covers from Dylan are such important events. It is the stamp of quality. A chance for Dylan to recommend a song from his catalogue of favourites.  

He pilfered the American Songbook for its quality releases and now has a chance to cover the contemporary artists whose works we often overlook. For The Grateful Dead, Stella Blue is not the obvious choice. It is no Touch of Grey or Ripple but it is a fitting inclusion for the Dylan live sets. It boils down to liking the song, paying tribute to Garcia and making up for the time we lost listening to Dylan and the Dead. Despite their success together when touring Dylan and the Dead, the lacklustre live album release is still a sour note. It is one in a number from the end of the 1980s, a period less than stellar for Dylan and The Dead. Neither seemed capable of riding through the lull in interest and as a result, their sound seems to chase after inconclusive and ultimately irrelevant, time-limited sound.  

But there are ways of setting this right and Dylan is doing so with these Stella Blue performances. Give the studio recording a listen and it sounds pleasant enough. Robert Hunter and Jerry Garcia had a classic on their hands, one of many. Stella Blue has the blues right at its heart, as does the rest of Wake of the Flood. Get a grip of Mississippi Half-Step Uptown Toodeloo and you can hear the slick guitar work Dylan would have his touring band deploy on stage. It is as consistent a sound as The Dead would have wanted for their work if it is to be ripped through on stage, decades after it was first released. Dylan feels a connection with The Dead which, if their rejection of his application to join the band is to be believed, was not reciprocated entirely.  

Yet the joy in performing the track on stage, from the first go of it in Barcelona to the more refined and permanent Outlaw Music Festival setlist, is still there. Those performances, like any artist playing on into their eighties, are tinged with a sense of reflection. Dylan has done well to avoid the obvious pitfalls of looking back but did so as a way of identifying the differences between the America of his youth and the country in its current state on Rough and Rowdy Ways. Part of it feels like a war of exorcising the loss felt at the time, the drifting man trying to deal with the Mr. Mumbles tag. It would be some time before Dylan shook off the unimpressive run of album features after Dylan and the Dead. Oh Mercy is more a luck-based masterclass than anything which kickstarted a consistent rise like Time Out of Mind did.  

Like many parts of Dylan’s discography, we will never know the details of why Stella Blue has made its way into the setlist. For the most part, we can speculate and connect what few dots are available, assuming this link or that nod where we can. Ultimately it matters not why Dylan performs this song live, and with such frequency, but what he achieves in doing it. He keeps the memory of his time with The Dead alive despite some, like Garcia, having died some years ago. It takes a lot to get to this point in the life of an artist but once the reflection of other contemporaries takes hold, it never quite loses its place. It is not just Stella Blue featuring so frequently in the live shows from Dylan but a multitude of The Grateful Dead pieces which all feel as fresh and fitting on stage as they did in the hands of the original artists. Dylan pays tribute to plenty of deceased musicians on stage, but perhaps the most prominent of all is the band which was always keen to work with him, but never too intimately.