Flagging Down the Double E's

Flagging Down the Double E's

Bob Dylan's First Time Playing with the Grateful Dead (by Jesse Jarnow)

Volume 2: Rubber Bowl, Akron, Ohio, July 2 1986

Ray Padgett
Jul 02, 2026
∙ Paid

Today, part two of Grateful Dead scholar Jesse Jarnow’s miniseries on Dylan and the Dead 1986 (here’s the first if you missed it). The short five-show Dylan-Heartbreakers-Dead run travels to Akron, Ohio.

Notably, this is the first show ever where Dylan actually sits in with the Grateful Dead—the first time he’s playing in the band, before he will full-time the following summer. They do three songs together in Akron: “Little Red Rooster,” “Don’t Think Twice It’s Alright,” and “It’s All Over Now Baby Blue.”

Here’s Jesse to break it down:


Dylan and the Dead ‘86: Rubber Bowl, July 2nd

by Jesse Jarnow

No, really, these shows were Big Deals. People camped out in the parking lots to see Bob Dylan and the Heartbreakers share a bill with the Grateful Dead. Newspapers treated it as a generational soiree. The Deadheads were guaranteed to bring the party (and the acid) on an equally massive scale. The bigger venues also required promoters to sell many more tickets, which spiraled into needing to make ads like the above.

Local news not only dispatched crews to the parking lot of the Rubber Bowl for all-day coverage, but people cared enough to tape and preserve the coverage. There are several YouTube footage compilations like the one below, all with good larfs. Highlights of this reel include an interview with a young gentleman who figures it’s his last chance to see Dylan, a failed attempt to cut live to the concert from the news room, and a few minutes of Dylan and the Heartbreakers doing “Clean Cut Kid” while Dead roadie Steve Parish carries Jerry Garcia’s guitars onto the stage and glares at the crowd from just behind Tom Petty.

The two tours had briefly diverged after the Metrodome gig. Dylan and the Heartbreakers headed to Alpine Valley in Wisconsin for a Friday show, before the Dead took over the next afternoon for daylight shows at the same venue on Saturday and Sunday. They alternate headliners when the tours reconnect, and Dylan and the Heartbreakers go on first in Akron, playing to a less than sold-out crowd, but sounding fully enthusiastic. It’d been five years since Dylan toured the States, eight since a non-Christian tour, and over a decade since he’d played in the States like a normal large-venue rock act. Dylan and the Heartbreakers’ sets from Akron are only on cruddy audience tapes. Still sounds better than the Metrodome, though.

One thing the outdoor Dylan/Dead shows shared with the ‘60s festivals was that they became struggles for survival. And the heat got more intense as the tour progressed. “I hope the naked dude walking down the stairs got home OK,” reads one archive.org scene report from the Rubber Bowl. And many memories note what’s confirmed by the above video, which is that in deep summer heat, Bob Dylan takes to the stage in leather pants, fingerless gloves, a scarf, and a patchwork-adorned jacket of perhaps some genetic relation to the Hearts of Fire one. A few Deadheads posted memories about mistiming their LSD doses, thinking the Dead are playing first and finding themselves accidentally peaking as Dylan and the Heartbreakers run down “Band of the Hand” and other 1980s faves.

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