Diamonds From the Deepest Ocean :: Bob Dylan | Blown Out On The Trail

Diamonds From the Deepest Ocean is a new series exploring classic Bob Dylan bootlegs from the CD era. Before broadband internet, YouTube, and bottomless hard drives overflowing with FLACs, many Dylan fans relied on the grey market to gain entry into the world of unreleased Dylan. This series celebrates those tangible treasures and wonders: “What’s lost when you can have it all?”

The 2023 Bob Dylan live show was longer than the performances he gave thirty-five years ago, in 1988, during the first year of what became the Never Ending Tour (NET). The shows were longer in time—Dylan plays for about an hour and forty-five minutes these days, whereas the 1988 shows were almost always under 90 minutes—and in setlist—seventeen songs instead of fourteen or fifteen, typically. Of course, the energy is different. The “Rough and Rowdy Ways World Wide Tour” of 2023 was heavy on shadows and atmosphere, with a serious and vaguely sinister edge. The 1988 shows were more straightforward. For that tour, Dylan took a small rock combo on the road, turned up loud, and played fast.

That much is clear just twenty seconds into Blown Out on the Trail, a fantastic soundboard bootleg that captures Dylan’s performance at Jones Beach, New York, on 30 June 1988. It sounds like Dylan is trying to match the 45 RPM speed of the original “Subterranean Homesick Blues” single, or even beat that record. Kenny Aaronson’s bass is machine gun thunder all through the song, and the show, and that first year of the NET. It is enough to make any fan of Live Dylan conjure “What If …?” scenarios with Kenny, not Tony standing next to Bob for the last three and a half decades. Christopher Parker’s drums replace subtlety with strength. G.E. Smith is pointed and fierce, even when the train shakes and wobbles on the rails. His recurring solos during “Masters of War” sound demented and feverish.

Bob Dylan plays this 1988 show like an impatient man with places to go, people to see. I suppose he was exactly that, with 3,186 (and counting!) concert performances waiting just ahead and down the road.

For commercial bootleggers, the length of Dylan’s 1988 show posed a problem, especially for those who plied their wares on compact discs. Whereas many early NET shows fit comfortably on the front and back of a 90-minute cassette—to the great thrill of tape traders, a totally different breed of Dylan aficionado—90 minutes is about ten too many for a CD. Capturing a complete show of that length requires a second disc, which is then left mostly empty.

Most commercial bootleggers used filler to balance their uneven discs. Filler is additional music, usually from another show, another time, another place entirely, meant to top off the media. It expands the bootleg to capture the entirety of the feature presentation and then entices buyers with something else and something more. Naturally, an expanded product requires an expanded price tag, as anyone who browsed the “Import” section at their local record store remembers.

Different bootleg programmers used the filler space in different ways. Many Dylan bootlegs have filler that highlights a specific tour leg or multi-night stand at the same venue. Those boots typically tack on songs that were performed one night but not the next. Some used filler to give listeners access to rarities and outliers like one-off performances or guest appearances. Those recordings might feature songs from many nights across multiple tours. Others tried to highlight a certain thesis or theme or component of the show, something that deserved special attention. That’s the approach you’ll find on disc two of Blown Out on the Trail

In this case, the thesis is not complicated or controversial. It’s almost an early NET truism: the best part of Dylan’s breakneck 1988 shows were those moments when everything slowed down, when Dylan let the rhythm section take a breather and stepped out with just G.E. Smith and an acoustic guitar. Together they played old songs from Dylan’s early albums but also songs that were just old. One of the Jones Beach performances is “Lakes of Pontchartrain,” a song that probably dates to the late 19th century. You can trace another song performed that night, “Eileen Aroon,” through Tommy Makem and the Clancy Brothers in 1966 to Gerald Griffin, an Irish poet and lyricist who died in 1840, and then further still, back along a murky timeline that stretches all the way to the far side of the 15th century. 

Nostalgia plays a role here, with Dylan standing almost alone with an acoustic guitar playing folk songs in a fashion very similar to his earliest popular persona. Surely the audience noticed that callback, even those who did not recognize it as a real-time example of the folk tradition and a musical continuum stretching endlessly in all directions. That timeless feeling is captured in breathtaking quality on Blown Out on the Trail. The bootleg CD appeared in 1996 on an obscure label called Moontunes, purportedly out of Luxembourg. Moontunes had a partnership with The Razors Edge, another bootleg label that specialized in Dylan discs, along with titles by Richard Thompson, Elvis Costello, Morrissey, and Mathew Sweet.  

The filler included with Blown Out on the Trail offers even more evidence of the quality and energy of the 1988 shows, and the anachronistic power of the acoustic segment. It includes the complete half-hour set Dylan performed at the second Bridge School Benefit on 4 December 1988. It also presents highlights from Dylan’s 31 August 1988 show in Syracuse, New York. 

Those are inspired filler selections because they again underscore the beguiling folk mystery of Dylan with an acoustic guitar beside the ramshackle breakneck energy of the electric set. The Bridge School performance begins with a fun warm-up take on Jesse Fuller’s San Francisco Bay Blues and continues with Woody Guthrie’s Pretty Boy Floyd. The Syracuse set includes an acoustic Barbara Allen—a song that dates to before 1666 and might be a mocking tribute to the mistress of King Charles II—and an electric I’ll Remember You, a drum-heavy Dylan original that was about four years old in 1988. 

It is enthralling, all of it, and the perfect reminder that filler does not have to be a mindless effort aimed at taking up space and time. Filler can also be an object lesson, a demonstration, the very embodiment of space and time, and a reminder that some performers are so powerful that they can suspend them both, or even make them run backwards. | j adams

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