Bob Dylan and Grateful Dead – Philadelphia 1987 Review

Almost every bootleg of the 1987 tour Bob Dylan and Grateful Dead took part is better than the official release. Dylan and the Dead was a disaster for a multitude of reasons, not least because it features Dylan at a low point in his recording career. But the performances preceding and following it are of a much higher class. Philadelphia 1987 may seem like just another date on the road, but there is certainly a massive difference at play. Cause for celebration from bootleg listeners comes in the form of The Ballad of Frankie Lee and Judas Priest debut, but also hearing some more recognisable songs. Tangled Up in Blue, Ballad of a Thin Man, and Chimes of Freedom can be found in this show. It’s quite the contrast to those Gotta Serve Somebody and Joey features on Dylan and the Dead.  

Those songs are not the problem, just the performance, which happened to be released. Philadelphia 1987 is a step up in quality. Dylan still sounds breathless, staggering from one line to the next on opening song Tangled Up in Blue. Paired with Grateful Dead members, though, and the songs have a new instrumental depth. Bob Weir and Jerry Garcia’s guitar work makes all the difference. They amplify songs which, at this point in Dylan’s time on tour, had become flat. Songs that had been ripped through by an uncomplimentary rock and roll aesthetic. A few highlights precede this tour, particularly the tour with Tom Petty and The Heartbreakers, but it was clear Dylan needed to use other big names, capable on-stage musicians, as a crutch for his artistic shortcomings. Philadelphia 1987 is a highlight of the burnout period, where Dylan was struggling to match the menace of his very best songs with a performance worthy of tackling them.  

Delightful work can be found on Philadelphia 1987. It is a stark contrast to a few other shows Dylan carried out in the mid-1980s. Garcia on lap steel for a moving rendition of I’ll Be Your Baby Tonight and the rocked-out punch of All Along the Watchtower is often a victory. Part of the charm for these versions is hearing how much Grateful Dead can add without imprinting their psychedelic-tinged work. They were, first and foremost, exceptional musicians. Though issues around professionalism and artistic clarity would hound them their whole careers, they sounded comfortable on stage. No wonder they swore off the studio when they could back Dylan across some improvised-sounding hits. Delicacies like Stuck Inside of Mobile With the Memphis Blues Again and Queen Jane Approximately, the latter with a false start too, shine a light on the liveliness Dylan had lacked throughout this decade. 

He would turn that corner just a few years later with Oh Mercy. The tours leading up to its release were shaky, but when he was with Grateful Dead, he was usually at his best. Rehearsal tapes and live bootlegs like this are better than the official release. It is one of the many reasons bootleggers must continue. Where else could we find the groovy sound of Man of Peace or the Garcia-led Touch of Grey, the latter closing out the album and relegating Dylan to guitar after a hard shift of vocal work. Staggering instrumental work from Garcia and Weir is what elevates Dylan, and the rest of The Dead are as impressive as ever. Philadelphia 1987 hears the band and Dylan perform with a groovy step towards greatness.