It Takes a Train to Wreck

1986-07-07, RFK Stadium, Washington DC

Flagging Down the Double E’s is an email newsletter exploring Dylan shows of yesteryear. If you’ve found this article online or someone forwarded you the email, subscribe here to get a new entry delivered to your inbox every week:

Today, the final guest newsletter of my little jury-rigged paternity leave comes from the great Rob Mitchum. As anyone who read my first post back in January might remember, Rob’s Phish newsletter was a key inspiration for this one - not just the format, but also his way of writing that welcomes the curious and superfan alike (I don’t much like listening to Phish, but I sure enjoy reading Rob write about ‘em!). Even more relevant to today’s show, Rob co-hosts the excellent Grateful Dead podcast 36 from the Vault with Steven Hyden, which resumes next week.

On February 13, 1989, the Grateful Dead offices in San Rafael, California received a surprising phone call. On the line was Bob Dylan, one of the band’s idols, politely asking if he could join the group on a permanent basis. The night before in Los Angeles, Dylan had sat in for the Dead’s second set, playing mostly anonymous rhythm guitar in the dark and only singing a full lead vocal for the “Knockin’ on Heaven’s Door” encore. The Dead put Dylan’s request to a vote, requiring unanimous agreement to pass, and somebody (likely eternal killjoy Phil Lesh) said no, splitting Dylan and the Dead onto two very different tracks for the 1990s. 

Dylan’s sudden urge to play sideman in the Grateful Dead has to be one of the most baffling decisions in a career full of them. Putting aside for a moment that he’s BOB DYLAN, the track record of his ‘80s collaborations with the Dead were and are hardly considered successful. That 1989 sit-in may have been the most tolerable of their public performances, because it was merely a head-scratcher and not a total disaster. Practically nobody fondly remembers their 1987 tour together or its 1989 “highlights” record Dylan & The Dead (though there are quite a few fascinating and/or great moments on the rehearsals). 

Then there’s their first official intersection, five shows in the summer of 1986 where Dylan and the Dead split the bill and twice shared the stage. The concerts were a temporary merger of two separate tours, the Dead’s annual summer jaunt through favorite venues such as Berkeley’s Greek Theater and Wisconsin’s Alpine Valley and Dylan’s global “True Confessions Tour” with Tom Petty & the Heartbreakers. In Minneapolis, the Dead played a rare-for-the-time single set opening for the homestate hero in the first-ever concert at the Minnesota Vikings’ stadium the Metrodome (where the acoustics were just as bad as you might imagine). Then the acts reconnected for four co-headlining stadium shows in Akron, Buffalo, and Washington DC, with Dylan & The Heartbreakers going first each night, or rather, afternoon — these shows were long, man.

Dylan joined the Dead for a few songs twice that week, July 2nd in Akron and July 7th in DC. The first of those appearances is generally regarded as historically significant and musically decent. The second, today’s, is considered one of the worst Dead shows of all time — which is really saying something for a band that is famously uneven and only grew more so in their final decade.

That’s not entirely Dylan’s fault, though he shoulders some of the blame. Three days after this show, Jerry Garcia fell into a diabetic coma, forcing the Dead off the road for the first time since their brief mid-‘70s hiatus. The extreme temperatures of the day and the unforgiving stadium environment certainly did not help — you can hear Jerry’s energy flagging by the end of the opening “Ramble On Rose” — and the Dead played a shockingly short show by their standards, falling well short of two hours over their usual two sets, some 50 minutes less than the “opening” Dylan/Heartbreakers marathon. 

Eighteen of those minutes are performed with Dylan on third guitar and vocals, joining in for “It’s All Over Now, Baby Blue” and “Desolation Row,” two of the many Dylan songs covered by the Dead. The chemistry is palpable, if by chemistry you mean mixing together some chemicals that emit a foul stench. Dylan breaks a string almost immediately, and his replacement guitar sounds woefully out of tune and lost in the Dead’s esoteric stew. About 4 minutes into “Baby Blue,” Dylan decides it’s a duet now, yelling over Jerry for the rest of the song. “Desolation Row” fares about as well, with the Two Bobs stomping all over the song’s poetry in a hammy frontman competition. By the end, both of them are struggling to sing from laughing, and you might be chortling right along. 

“I found myself in the weird position of teaching Dylan his own songs. It’s just really strange!,” Garcia said of these sit-ins in Blair Jackson’s biography. “It was funny. He was great. He was so good about all this stuff. Weir wanted to do ‘Desolation Row’ with him, y’know, and it’s got a million words. So Weir says, ‘Are you sure you’ll remember all the words?’ And Dylan says, ‘I’ll remember the important ones.’” 

1986 is an interesting time for both Dylan and the Dead. Both are at a commercial ebb: despite the high-profile co-billing, these shows weren’t sellouts. For the Dead, these stadium shows foreshadowed their post-”Touch of Grey” future, but by the time of Jerry’s coma, they were treading water creatively, without a new studio album since 1980’s Go To Heaven. Dylan, meanwhile, was going through the same midlife identity crisis as so many of his 60s peers, casting about for any way to engage with ‘80s pop culture and wearing black motorcycle leathers in the 100-degree sunshine. 

The choice of The Heartbreakers was about as harmless a move as possible for Dylan to commandeer musical trends of the time, but apart from the always-remarkable keys of Benmont Tench, they’re fairly generic backers on the opening set here. For the 50,000+ in attendance at RFK, Dylan adopts a shouty style that comes off as pretty strained, particularly in contrast with Petty’s laid-back stoner charm in the Heartbreakers mini-sets (at one point he lets the crowd take a verse of “Breakdown,” then playfully chides “Wait a minute, wait a minute, I want to sing this verse.”). Add in heavy-handed backing vocals from The Queens of Rhythm and poor stadium acoustics, and the two-and-a-half-hour set is a shrill, exhausting listen, though it arguably gets better as the summer heat wears down Dylan’s over-exuberance.

So even though Dylan would go on to tour with the Heartbreakers again in Fall ‘87, I can kind of understand his head being turned by the other band on the bill. Say what you will about the flaws of Stadium Dead, but they certainly didn’t compromise their sound for the bigger crowds, keeping their setlists irregular and codifying their most experimental instincts into the nightly “Drums/Space” segment. And given that one of the Dead’s many identities over the years was “Very Solid Bob Dylan Cover Band,” sometimes playing as many as three Dylan classics in a single show, it wasn’t hard for Dylan to imagine himself among their ranks. 

Yet it’s equally obvious why the pairing didn’t work, either here or in the summer of ‘87. My non-expert impression of the Never Ending Tour is that it’s Dylan leading a series of exceptionally versatile and professional bands able to morph to his every whim — a description that is miles away from the Dead’s strengths. Rehearsal was never in the Dead’s vocabulary, and the band’s notorious inconsistency can be chalked up in part to their democracy, with Jerry the least-decisive bandleader possible, for better or worse. Introducing a headstrong Dylan, even if he was trying to take a background role, never would have worked in the long run. Filmmaker Len Dell’Amico describes their ‘87 tour relationship as such in the oral history This Is All A Dream We Dreamed: “The Dead is like an orchestra, and I think it was difficult for him to assert himself with six guys who had a very set way of doing things.”

In the end, sporadically co-existing was a better strategy for both parties. In 1995, the Never Ending Tour intersected with the Dead’s “tour from hell,” their star-crossed final trip around the country before Jerry Garcia’s death. Dylan and His Band opened five shows that summer, including a return to RFK Stadium where Garcia sat in for “It Takes a Lot to Laugh, It Takes a Train to Cry” and “Rainy Day Women” at the end of Dylan’s set. It’s pretty great, with Jerry’s gentle leads flitting around the former song’s blues stomp, and it leaves the often troublesome Dylan & the Dead combination with a surprisingly good aftertaste. 

1986-07-07, RFK Stadium, Washington DC - Dylan set

1986-07-07, RFK Stadium, Washington DC - Dead set (via

Find the index to all shows covered so far in this newsletter here.