The surreal tale of Bob Dylan, HBO, and a slapstick comedy that never was

The life and times of Bob Dylan have been as surreal as they come, filled with notable anecdotes brimming with comedy. In the late 1990s, Bob Dylan developed a bizarre new fixation: slapstick comedy. Primarily influenced by the works of Jerry Lewis, ‘The King of Comedy’, which he would watch obsessively on his tour bus, Dylan became monomaniacal about the genre. He couldn’t shake the feeling that he should write and star in an HBO series delving into this comedic world.

To bring his vision to life, Bob Dylan enlisted Seinfeld writer Larry Charles, as Charles recounted during an appearance on comedian Pete Holmes’ You Made It Weird podcast. This surreal tale paints the songwriting genius in a hilarious light, leaving fans to wonder what the potential HBO series, which nearly came to fruition, might have looked like.

Describing the idea of Dylan writing and starring in the potential comedy series as “almost like a Buster Keaton” move, Charles revealed that he agreed to meet the musical icon. He struggled to believe was actually happening. How do you go from ‘Blowin’ in the Wind’ to slapstick?

At the time, Charles thought it was fantastic news, but he was primarily hoping to have one meeting with Dylan just so he could tell his friends, not expecting anything to really come of it. In truly peculiar fashion, he met with Dylan in a cubicle at the back of a boxing gym in Santa Monica, reminiscent of a capo and mafia don devising their next criminal enterprise.

The troubadour smoked constantly throughout the meeting, filling the booth with cigarette fumes. Yet, this strange scene was about to get much weirder, with Dylan’s naturally comical personality quickly coming to the fore and astounding Charles. The gym was attached to a coffee house, so at one point, before they got into the minutiae of the potential project, Dylan’s assistant asked if they wanted any drinks.

Charles ordered an iced coffee, and the raspy Dylan mandated: “I want something hot; I want a hot beverage.”

Bob Dylan - 1965 - Highway 61 Revisited album cover
Credit: Far Out / Sony Music Entertainment

However, when they were served, the musician immediately grabbed the iced coffee and started glugging it. Blown away, Charles just watched the troubadour necking his drink, seemingly undeterred by the fact that it wasn’t his and certainly wasn’t hot. The coffee he ordered sat untouched, piping in the middle of the table.

Just as he’d nearly finished the iced coffee, Dylan looked surprised and asked Charles why he wasn’t drinking his own drink, to which he was told that he was drinking it. The ‘Like a Rolling Stone’ songwriter laughed, and the ice was broken.

Following this faux pas, Dylan – whom Charles described as being like “a sorcerer” testing him – brought out an ornate box, opened it, and dumped a pile of scrap paper on the table. Every piece of paper was from hotels across the world that he’d stayed in when on tour, with lines, names, and ideas scribbled on them.

“I don’t know what to do with all this,” Dylan conceded. He was informed that they could compile them all like he would with the cut-up technique in songs. That was the beginning, and eventually, they synthesised the ideas into an elaborate treatment for a surreal slapstick comedy. When the treatment was finished, Dylan was told that HBO wouldn’t turn him down because of his stature, so he agreed to meet with them. What ensued was comedy gold.

They were an unlikely pair. Charles, who was in the habit of wearing pyjamas everywhere at the time, with really long hair, fully embodied The Dude as he turned up for the HBO meeting. As for Dylan, he offered a counterpoint. Wearing a black cowboy hat, duster and boots, the musician looked ready for a gunfight at the O.K. Corral.

After they entered the room, HBO CEO Chris Albrecht excitedly said to Dylan, “Look, I have the original tickets from Woodstock,” to which the bewildering musician responded, “I didn’t play Woodstock”. He then walked to the other side of the office, peering out the ceiling-high windows looking over New York. Miffed by the Woodstock comment, he had his back to the rest of the room for the entire meeting, leaving Charles to pitch the treatment. This behaviour led Charles’ manager, Gavin Polone, to whisper, “He’s a retarded child.”

Despite everything, HBO bought the project. There was one last twist in the tale, though. After the meeting, when in the elevator, Dylan’s manager, Charles and Polone were elated, but the musician had the final say. He turned around to them and said, “I don’t wanna do it anymore; it’s too slapsticky.” That was that. It fell apart as though the pitch itself was the slapstick pit Dylan was hoping to itch.

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