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The funny side of Bob Dylan: Five comical tales from the life of the folk legend


Bob Dylan was already a joker when he entered the fray, fooling journalists into thinking that he was a runaway child of the circus, and he continued to learn thereafter not to take life too seriously. As he croaked when the 1960s got a little too humourless for him and he set about reclaiming his freedom, “Ah, but I was so much older then, I’m younger now.”

Albeit he is a pretty private individual, anyone who has heard his witty and whimsical Theme Time Radio show can attest, he is and always has been one hell of a character. Mildly absurdist and drier than Oscar the Grouch’s bathmat, you shouldn’t let his spiritually sagacious and serious side fool you into thinking that there’s not a sly smile underneath.

After all, when Joan Osbourne supported him at the Irving Plaza she finished her set and went to the back of the 2,000 strong crowd to enjoy a drink at the back bar and appreciate Dylan’s set from afar. Only for Dylan to call out mid-set, “I’d like to thank Joan Osbourne. Joan and I are going to sing a song.” When the shocked singer began wading through the crowd towards the stage, Dylan casually added, “…but not tonight.”

Aside from such gags, he has also landed himself in some scrapes too. Below we’ve curated these wacky incidents to give you a snapshot of some of the strangest happenings in the folk star’s life. However, it would seem that ultimately they could quite simply be summed up as Dylan just doing Dylan stuff. 

Five comical stories from Bob Dylan’s life:

The ghost dog encounter

When Bob Dylan wanted a break from the harsh limelight while he was touring England during his electric Judas phase, he met up with his old pal Muff Winwood and casually began discussing ghosts. The American troubadour for some reason figured that there’d be “some good ones in England,” because, as we all know, there are inexplicably more ghosts from Victorian-era Britain than from any other place or period in the long history of humans dying. 

Fortunately, Winwood had heard some mystic tale through the grapevine that there was an old, abandoned house nearby, and as fate would have it, the locals believed that it was haunted by the ghost of a dog. Naturally, Dylan is chomping at the bit when he hears this enticing tale and they all hotfoot it over to the typical delipidated spectre abode for a curious poke around its darkened dominion. 

Now, as Winwood writes in Wanted Man: In Search of Bob Dylan, at one point during this auspicious evening, they hear a dog bark. “Now this is likely to happen in the countryside in Worcestershire,” he humorously and, indeed, correctly remarks. “But Dylan is convinced he’s heard the ghost of a dog! He was like a little kid running up to you, grabbing you by the arm, going, ‘This is unbelievable!’” Unbelievable certainly being the operative word.

Whether or not the howl from the Worcestershire underworld/countryside affirmed a lifelong belief in the undead for Dylan is unknown, but it’s categorically confirmed that he caught a bad case of the Pomeranian home spooked blues that evening. 

(Credits: Far Out / Alamy / Joyce McCown / Fabian Wiktor)

Mistaken for a homeless man

The original vagabond by name, the original vagabond by nature. It is a universal oddity within music that everyone who has met Dylan has inexplicably labelled him scruffy, but that might be with good cause. After all, in Long Beach, New Jersey in 2009, he was identified by police as a possible “scruffy old man acting suspiciously” on the loose.

Dylan was simply out taking a stroll around town, no doubt regaling himself with impressive thoughts about how “the flowers of the city though breath-like, get deathlike sometimes.” However, a patrol car then successfully identified the wayfaring troubadour as fitting the description of their suspect. Therefore, they pulled over and apprehended a flummoxed leading figure of cultural history. 

Dylan was without any ID at the time, but quite inexplicably, he didn’t seem to kick up a fuss or offer to take them to a record store to prove that he was, in fact, the voice of a thousand generations and not some surly tramp up to no good in a nice quiet little beach community. 

Apparently, Dylan casually informed officer Kirstie Buble that he was in town to headline a concert with Willie Nelson and John Mellencamp. She did not believe the drenched geriatrics tall tale, later stating: “I’ve seen pictures of Bob Dylan from a long time ago and he didn’t look like Bob Dylan to me at all. He was wearing black sweatpants, tucked into black rain boots and two raincoats with the hood pulled over his head.” 

At this point, he was driven back to his hotel where he was, in fact, able to identify himself as a world-changing cultural icon. And the case was put to bed. The police had evidently identified the wrong fellow and the “scruffy old man acting suspiciously” was still be at large. Or was he? The police later came to the conclusion that it was likely Dylan who had been acting suspiciously all along, although Dylan pleaded that he had just been “out for a walk.” It subsequently came to light that the folk star may well have been out in the pouring rain looking for the house where Bruce Springsteen wrote ‘Born to Run’.

Credit: YouTube

Sleeping in Neil Young’s coffin

The fact that Neil Young drove around in a 1948 Buick Roadmaster hearse called Mortimer Hearseburg or simply Mort among friends, is an oddity in itself, but even odder is that Dylan almost died in the back of it. You see, Dylan found the vehicle parked up at Young’s ranch and was captivated by its curious allure. His next step, however, was a pretty peculiar one. Wandering the ranch grounds alone and feeling weary, the folk forefather inexplicably decided that he would climb into the back of it to take a nap. 

It goes without saying that it was a bizarre place to take a snooze, and as Sandy Mazzeo explains in the Neil Young biography, Shakey, it almost had dire consequences. Later that day, Mazzeo got behind the wheel of the hearse to take it for a spin for an unspecified reason. Then all of a sudden, he hears repeated loud bangs and gravelled voiced groans, which when driving a hearse proved understandably disconcerting. 

As Mazzeo explains: “I’m thinking, ‘Oh my God, it’s a ghost’. I look in the rearview mirror, and it’s Bob Dylan.” The twist, however, was that this was during Dylan’s rather outlandish turban phase – an interesting phase for anyone other than a religious convert to go through – and this only furthered the ghostly illusion. “He’d slept in his turban and it had come all undone – he looked like a mummy!”

Fearing that the morbid past of Mort had finally caught up with it, Mazzeo believed that he was genuinely in the presence of the ghost of folk past, and this introspective apparition almost caused him to run the car off the road. In the cavernous tomb of the back of a hearse without a seatbelt in sight, a collision would no doubt have left the turban-wearing troubadour lying in repose.

(Credit: YouTube)

Turned away from his own concert

2001 was a year when security was on high alert all around the world. Thus, when a shifty little miscreant was floating around outside of a Bob Dylan concert he was promptly turned away, only for it to later emerge that the suspicious vagabond up to no good was due to grace the stage that very evening. Dylan had requested stricter security but being turned away from his own concert is not what he had in mind. 

Dylan was touring in the States following the release of the album Love and Theft, part masterful return to form, part dubious plagiarism oddity. He was due to end the tour at Oregon’s Jackson County Exposition Center when he approached security without his backstage pass and three security guards in their 30s turned away the fabled voice of a generation. 

Naturally, Dylan was somewhat miffed by the incident and claimed that the performer doesn’t tend to put themselves on the guestlist, especially when the performer in question is one of the most renowned and revered artists ever to grace the Earth. When Dylan’s security director clocked the incident a few choice words were exchanged, and an ‘incident’ ensued. 

Later when reflecting on the bizarre situation, venue manager Chris Borovansky stuck to his guns and boldly declared: “He said no exceptions. Absolutely none.” While the whole bit seems like a skit from a Coen brothers movie, Dylan and his security team apparently credited them for their due diligence after apparently initially demanding that the arduous security guard be thrown off-site. 

Staying true to character, Borovansky later added: “We prefer the term ‘relocated’. But in the end, he later said that the guards did a great job.” After a minor, comedic delay, it was agreed that the wild-haired old man was, in fact, the same wild-haired old troubadour set to perform that evening.

(Credit: Netflix)

Picking up hitchhikers

Bob Dylan was thrust towards a level of fame barely known by musicians at such an early age and so rapidly that he was suddenly spun out by it. However, when you’ve been perched at the lofty peak for a while, you can be a bit more wily with the way you navigate it. In the end, Dylan eschewed the full glare of fame and found a way to do Dylan things all the same. 

During his born-again Christian phase of the late 1970s / early 80s, he embarked on a particularly singular hobby. When Dylan was delving fully into the realm of Christianity, Keith Green was the foremost musician in this circle. In fact, Green had even been described as the Christian John Lennon

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In the Biography No Compromise: The Life of Keith Green, there is a section when Green’s wife, Melody, recalls that Dylan would drive around with her late husband. “He told us that he loved to pick up hitchhikers and tell them about Jesus. They never recognised him because they drove a beat-up old car and he wore a knit ski hat over his famous curls,” she writes.

With a dented fender and the car strewn with a hoarder’s slew of knick-knacks and throwaways; the unsuspecting hitchhikers overlooked the driver sharing Dylan’s voice of sand and glue or else they found the whole thing a little too wild to reconcile. Thus, Dylan was free to simply plough along the long roads with his friend extolling the world of Christ as he pleased. You can only imagine the wry smile he would’ve sported if he had popped up on the radio.

(Credit: YouTube)

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