“How Long Can We Falsify and Deny What Is Real: Bob Dylan Is the Funniest Person Alive, and Why We Need to Talk About It.” World of Bob Dylan 2023, June 2023, Tulsa, OK.

BY Harrison Hewitt


I’d just like to say before I start that it’s one of the pleasures of my life to be able to be in this room with you people today – to talk about Bob Dylan. Bob Dylan, who wrote “Desolation Row.” “Desolation Row,” which is my favorite song. I’ve said if “Desolation Row” were the only song on Highway 61 Revisited, Highway 61 Revisited would still be my favorite album. If “Desolation Row” were the only song Bob Dylan had ever written, Bob Dylan would still be my favorite artist. That’s how much I love “Desolation Row.”

If you listen to the earliest live performances of “Desolation Row,” there’s something interesting that happens and that is that the audience reacts like it’s Def Comedy Jam in 1992 and Bob Dylan is Bernie Mac. The crowd reacts like it’s the funniest thing they’ve ever heard in their lives. They’re losing it after almost every line, and Dylan – far from being unsettled – is loving it. Not physically possible, I suppose, but you can hear him smiling.

Anyway, what’s my point with this? Good question. I hope I remember. Here it is: Dylan has played “Desolation Row” well-nigh 600 times. And it’s only in those early performances that the audience reacted this way. What changed? The song didn’t change. Okay, that’s not exactly true; in later years Dylan would omit certain verses – most notably the verse about the mermaids because, as Allen Ginsberg relayed, Dylan came to view the imagery in that verse as “dopey.” But the point is the essential character of “Desolation Row” has not changed. Don’t get me wrong: I’m not saying “Desolation Row” is “Hello Muddah, hello Fadduh, here I am at Camp Granada.” It’s not a novelty song, it’s not a comedy song. I listen to “Desolation Row” every day and have for many, many years. It takes me up, down; makes me hot, makes me cold; makes me light, makes me heavy. Like Bob Dylan, “Desolation Row” is many things. But one of the things it is, is funny. And that’s the aspect that’s been lost, at least insomuch as you won’t hear an audience laugh at the funny lines anymore, the way they did when both the song and its author were young.

This, to me, is a metaphor for Bob Dylan’s career. There are surprisingly few explorations of Dylan’s sense of humor, and the ones there are tend to focus heavily – if not exclusively – on early Dylan. The implication being that at a certain point Dylan dropped the comedic side of his character and became a figure of great seriousness. Is that true? Did Dylan change, or is it the response to Dylan that changed?

I would submit it’s the latter. And I would explain it like this: If you go to a show and you hear something you think is funny and other people are laughing, you’ll be happy to join in. But if you go to a show that people say is super serious and important, even if something strikes you funny, you don’t want to be the one person who laughs because you’ll look like a goof. You’ll seem juvenile, shallow, like you don’t really understand or appreciate the gravity of what’s happening. In other words, the more Dylan was built up by the culture as a figure of great importance, the less folks were willing to admit that he’s funny, or even to recognize that fact.

It can also be a way of inflating oneself. If Dylan is this flesh and blood fella who’s cracking wise, then that can be easily appreciated. But if I elevate Dylan to be an artist who is so profound and so pure as to be untouchable, or at least to be somebody who can only be handled with white gloves – then I seem smarter for “getting” him. The more serious and important Dylan is, the more serious and important is the person who claims to understand and appreciate his work.

Well, I am not an important person, and I don’t care about being perceived that way. I’m quite happy to paddle around in the shallow end of the pool. And I encourage others to join me! Because it’s fun. Bob Dylan is a fun person. Bob Dylan is a funny person. Some would say Bob Dylan is the funniest person.

But why take my word for it. Let’s go to the quotes!

In 1965, Bob Dylan did an interview with the great Nat Hentoff, may he rest in peace, for Playboy magazine. The audio of this interview is out there, and it’s pretty straight. That is not the interview that appeared in the pages of Playboy. Here’s Nat Hentoff telling the tale:

There were two interviews. The first was really an almost unusually straight interview. As I recall, it was a quite sober, almost historical, biographical account, a lot of opinion, a certain amount of his – you know [Dylan] can’t avoid being sardonically funny, but just a straight interview. The galleys were sent to him and I don’t recall him making more than two changes of no significance. Then the final set came to him after they messed with it [at the Playboy offices] in Chicago. I don’t know what they did but I think they put some words in his mouth. They fooled around with it. I got a call and he was furious. I said, “Look, tell them to go to hell. Tell them you don’t want it to run.” And he said, “No, I got a better idea. I’m gonna make one up.” … He made up an interview. I helped, I must say. Some of the good straight lines are mine, but all the really funny stuff is his. It was run with absolutely no indication it was a put-on. I remember I saw him two or three times in the month or two after and he’d say, “Hey, when’s it coming out, when’s it coming out?” He thought it was a really funny caper, which it was.


Perhaps the most famous part of this put-on interview is when Hentoff asked Dylan what made him decide to go the rock ‘n’ roll route. Dylan responded:

Carelessness. I lost my one true love. I started drinking. The first thing I know, I’m in a card game. Then I’m in a crap game. I wake up in a pool hall. Then this big Mexican lady drags me off the table, takes me to Philadelphia. She leaves me alone in her house, and it burns down. I wind up in Phoenix. I get a job as a Chinaman. I start working in a dime store, and move in with a thirteen-year-old girl. Then this big Mexican lady from Philadelphia comes in and burns the house down. I go down to Dallas. I get a job as a “before” in a Charles Atlas “before and after” ad. I move in with a delivery boy who can cook fantastic chili and hot dogs. Then this thirteen-year-old girl from Phoenix comes and burns the house down. The delivery boy – he ain’t so mild: He gives her the knife, and the next thing I know I’m in Omaha. It’s so cold there, by this time I’m robbing my own bicycles and frying my own fish. I stumble onto some luck and get a job as a carburetor out at the hot-rod races every Thursday night. I move in with a high school teacher who also does a little plumbing on the side, who ain’t much to look at, but who’s built a special kind of refrigerator that can turn newspaper into lettuce. Everything’s going good until that delivery boy shows up and tries to knife me. Needless to say, he burned the house down, and I hit the road. The first guy that picked me up asked me if I wanted to be a star. What could I say?

Hentoff: And that’s how you became a rock ‘n’ roll singer?

Dylan: No, that’s how I got tuberculosis.

This interview fits squarely in the early period when it’s understood and accepted that Dylan could be funny, but I would argue that this spirit of playfulness, of Dylan approaching interviews as capers – is something that’s never left him.

And this is the part of the talk where I find myself struggling, because there is so much material I could include I don’t even know where to begin. If you print out every interview Dylan’s done, it’s about 1500 pages, depending on font size and spacing. And you can just about pick any one of those pages at random and you’re gonna find something funny.

In 1976, Dylan did an interview with Neil Hickey for TV Guide – one of our greatest periodicals – and Dylan was asked what kind of music he listens to… what records does he play for his own amusement?

Dylan said: “Personally, I like sound-effects records. Sometimes late at night, I get a mint julep and just sit there and listen to sound effects. I’m surprised more of them aren’t on the charts. If I had my own label, that’s what I’d record.”

In 1984, Dylan did a really long interview with Bert Kleinman, a career retrospective-type deal, that was cut up and formed the basis of a radio special called Dylan on Dylan. Also in the room was Artie Mogull, who as an executive at Witmark Music signed Dylan to a publishing deal back in 1962. Dylan is cutting loose the whole time, it’s great fun.

At one point he goes:

People say, well isn’t it great to be able to do what you do? Well, you know, yeah, it is to a degree; but you forget that touring performers, anybody that’s an artist, that’s out touring, that’s playing live from town to town night after night – you think that’s easy, it’s not easy! You think that people are having a ball? I mean, people talk to you on the phone: “What’re you doing?” “Oh, I’m in, uh, Schenectady.” “Oh yeah, well you’re having a great time, you know, I’m stuck here… in Orlando.”

My favorite Dylan interviews are the unofficial ones. The tapes of Dylan talking to reporters for print pieces, for example. The kind of interviews that weren’t done to be broadcast, so Dylan’s not doing his performative speaking voice, he’s just talking. You get a sense of the actual guy – in the moments between the moments.

In fact, somewhere along the line of that Dylan on Dylan deal, Dylan is so funny that Kleinman says to him: “You’ve been smiling a lot and laughing a lot here. You don’t do that much on stage. But you say you really enjoy yourself. You look so serious.”

Dylan goes: “Well, the songs take you through different trips, you see. I mean, how you gonna sing ‘A Hard Rain’s a-Gonna Fall,’ or ‘Tangled Up in Blue,’ or ‘With God on Our Side,’ or ‘Mr. Tambourine Man,’ or ‘Like a Rolling Stone,’ or ‘License to Kill,’ or ‘Shot of Love,’ or ‘Poison Love’ – any of that. How can you sing that with a smile on your face? It would be kind of hypocritical.”

Joni Mitchell told a great story, in an interview she did with Dave DiMartino for Mojo in 1998. She was talking about the Great Music Experience, this big concert in Japan that both she and Dylan played in 1994.

She said: “[Dylan] called me up just before we went over and he said, ‘I forgot how to sing – but I remember now, I remember now. The trouble is they want to me do all those Bob Dylan songs – and they’re so heavy.’”

Mitchell lamented that both she and Dylan have been typecast as solemn: “It’s like Meryl Streep at a certain point decided to do comedy. I’ve done drama, he’s done drama; we’ve done it very well. But we both have a sense of humor.”

In 1985, Dylan did an interview with Time magazine’s Denise Worrell, which was published in her book Icons. Dylan said: “There’s some humor in my songs. I don’t know, I think so. Some other people might not get it. I think there are funny things inside a lot of them. Some there aren’t. It’s kind of mixed up so much that I wouldn’t be one to just point and say, ‘This is funny.’”

As I say, that’s something Dylan said in 1985. A few years before that, in 1981, Dylan came out with a record called Shot of Love, which he has repeatedly called his favorite album. I don’t have time to get into that now, but I made a video about that which you can find on the www computer. Dylan has called Shot of Love his favorite album a half-dozen times. He’s never called any of his other albums his favorite even once.

One of the things Dylan said about Shot of Love was that the reason it got short shrift is that people didn’t understand what he was doing on that album. And I would argue nowhere is that more evident than in the reaction to “Lenny Bruce.”

“Lenny Bruce” is a song Bob Dylan wrote which appears on Shot of Love, as well as on every list of the worst Bob Dylan songs. You know, every site now is a repository of lists. I’m waiting for somebody to do a list of the Top 150 Bob Dylan Lists. And every list of bad Bob Dylan lyrics is an opportunity for the person doing the list to sneer at “Lenny Bruce” and talk about how incredible it is that Dylan could miss the mark that badly.

The line in “Lenny Bruce” that critics always cite as one of Dylan’s worst, most embarrassing, cringiest lines is when Dylan sings of Bruce: “Never robbed any churches nor cut off any babies’ heads.” And people say things like, “gee, Bob, rather faint praise, don’t you think? Might want to raise your bar for what constitutes an accomplishment, I’ve never mutilated any babies, maybe you’d like to write a song about me.”

Then there’s another line: “I rode with him in a taxi once / Only for a mile and a half, seemed like it took a couple of months,” Which people love to point out could easily be read as an insult.

Here’s the thing: Why are we assuming this was a misfire, instead of Dylan knowing exactly where he was aiming and hitting the target dead-on?

If we think of Lenny Bruce – the man, not the song – what are some words we could use to describe him? Well, “funny” would obviously be one, on account of he was a comedian. Another would be “outrageous.” “Shocking.”

Now let’s swing back to “Lenny Bruce” the song. What are some words we could use to describe the song? Well, “funny” would be one. “Outrageous.” “Shocking.”

So let me get this straight: Bob Dylan writes a song about a funny, outrageous figure, the song is funny and outrageous – and I am supposed to believe this was an accident? That those lines strike you and I and anybody who’s ever heard them as funny, but Bob Dylan – in writing the song, in recording the song, in singing the song on stage over 100 times – it’s never occurred to him that those lines are funny?

I don’t believe that. I don’t believe that for a second. I believe Bob Dylan knew exactly what he was doing. He knew Lenny Bruce lived on a lightning bolt – that Lenny Bruce took extreme chances, showed extreme courage, had extreme failings. So Dylan honors him by writing about him using extreme language. The line Dylan has about killing babies; Lenny Bruce said: “If there were absolute freedom, people would run over babies and charge admission.” Dylan is saying, “Yeah, but not you, Lenny. You were one of the good ones.” The whole song is like that. Dylan not only praises Bruce, he praises him in the language that Bruce spoke. It’s a clever song, and I applaud Dylan for not folding under the weight of everybody who says it’s stupid, or that it’s at best unintentionally funny.

You hear this all the time with Dylan – how unintentionally funny he is. Well what is more likely: that this guy has unintentionally stumbled into saying and doing funny things consistently for sixty years, or that he’s just a funny person who says and does funny things because it’s funny?

I would submit, every time you hear that Dylan said or did something unintentionally funny, you can subtract the word “unintentionally” and you’ll be closer to the truth.

The Philosophy of Modern Song is one of the funniest books I’ve ever read. You read the reviews, you’d never know it. It’d be one thing if critics said the jokes aren’t funny, but they reject the idea that they’re even jokes. Just a total negation of the whole tone of the book.

It’s like reviewing a Rodney Dangerfield show: “Mr. Dangerfield repeatedly stressed that he gets no respect. I find this hard to believe, he’s a comedian of great renown, well regarded by his peers.”

Or look at Rough and Rowdy Ways. Unlike The Philosophy of Modern Song, Rough and Rowdy Ways received good reviews, but again the funny bits got short shrift. You ask people to name funny bits in Dylan songs and the answers tend to be “The sun’s not yellow it’s chicken,” “They asked me for some collateral and I pulled down my pants,” or to take a later example: “Man says, ‘Freddy!’ I say, ‘Freddy who?’ He says, ‘Freddy or not here I come.’” Or people talk about the dad jokes Dylan would tell in his band intros. Joke jokes. I love all that stuff. But there are joke jokes and there are conceptual jokes. You listen to Rough and Rowdy Ways, or Tempest, and Dylan’s all over the place bludgeoning people and knifing them and mucking with their corpses. I for one find this very funny. Reminds me of Warren Zevon, who Dylan is a big fan of and who was a master of making the ridiculous seem grim and the grim seem ridiculous. It’s as if, after Zevon died, Dylan felt he had to take up the comically morbid mantle. And it’s particularly amusing in light of the fact that so many of Dylan’s peers are writing these moving meditations on their mortality, getting ready to make their transition from this world to the next. Meanwhile Dylan’s over here gathering gunpowder. Dylan’s saying: “If you guys want to die so bad, how about I kill you!”

In 2018, Dylan did an art exhibition called Mondo Scripto, for which he handwrote the lyrics to sixty of his most famous songs and then did a corresponding illustration for each song. The exhibition catalog contains a Q&A with Dylan, which to me reads like another Dylan caper where he’s supplying both the Qs and the As.

Those of you familiar with Mondo Scripto will recall that Dylan’s illustrations are very much on the nose. “Lay Lady Lay” has a line about a big brass bed – Dylan draws a big brass bed. There’s a lot of that going on.

As if anticipating that people might call these illustrations uninspired, the person questioning Bob Dylan – who may or may not be Bob Dylan – raises the point that the illustrations are “very literal,” thus allowing Dylan to explain that not only is this not uninspired, it’s extra inspired, and that it’s predicated on Mary Jo Bang’s translation of Dante’s Inferno with its corresponding drawings by Henrik Drescher. Which… say no more, Bob. Say no more.


This Q&A also includes other revelatory moments such as:

Did it take some time to figure out how [the songs] would be organised on paper?

It did, because the songs vary in length.

Do some songs lend themselves more easily to illustration than others?

The ones that are more visual do.


And my personal favorite exchange:

Was it difficult to come up with concepts for illustrations?

At first it was a bit of a dilemma, but then I started experimenting with other people’s songs. The Tom Petty song “Love is a Long Road” – I drew a picture of a dirt road. For the Billy Joel song “Moving Out” I drew a picture of a moving van. The Prince song “Darling Nikki” – I drew a picture of a young girl masturbating in a hotel lobby. I saw that, okay, it can be done, so then I did it with my songs.

Some of these responses call to mind another of my favorite semi-recent-ish Dylan interviews, and that was an interview Dylan did in 2009 to promote Hohner’s “Bob Dylan Signature Series Harmonica.” Dylan did this interview with the Director of Sales and Marketing for Hohner, Inc., and boy let me tell you it is illuminating. Keep in mind, the purpose of this interview was to promote the new Bob Dylan Signature Series Harmonica. Here are some of Dylan’s responses:

Does the harmonica play a role in your songwriting process?


How do you feel your harmonica playing has influenced today’s players?

I’m not sure it has.

Are there any young harmonica players today that capture your attention?

Not really. But I hope one comes along soon.

Of course I would be remiss if I left without mentioning what to me is Dylan’s comedic pièce de résistance, and that is an interview Dylan did while on tour with Carlos Santana in 1993. MTV sent a young reporter to speak with Dylan and Santana in Seattle, and rather than ask him about music, the reporter asked Dylan about pressing societal issues – because that always goes so well.

Do you think the availability of guns is a big problem today?

I don’t think there’s enough guns.

What about guns among kids? Do you think it’s just too prevalent?

Toy guns. There are moy toy guns than real guns, really.

Where do you think kids get these guns?

They get ’em in a toy store.

It is impossible to overstate how quick Dylan is with his responses here. Somebody might ask, where did he get these reflexes?

In 1968, Bob Dylan’s parents – Abram and Beatty Zimmerman – were interviewed by Robert Shelton. Really a fascinating document; Dylan’s father died a few weeks later so it’s not something that was or could ever be replicated. Anyway, there’s a section of this interview in which Shelton is probing to figure out how Dylan became such a skilled writer. And it inadvertently shows where Dylan got his comedy chops. It’s a print interview, so we can’t be certain of speed and inflection, but tell me this doesn’t remind you of somebody:

Robert Shelton: Was there anybody in the family that was a writer?

Bob Dylan’s Father: [pausing] No, outside of me there was no one.

Bob Dylan’s Mother: What did you ever write, a letter?

Bob Dylan’s Father: I could write if I wanted to write

I should say, in 2017, Dylan was asked by Bill Flanagan – in an interview posted on Dylan dot com – about the idea that he was the “jester” in Don McLean’s “American Pie.” Dylan did not take kindly to this idea.

In Don McLean’s “American Pie,” you’re supposed to be the jester.

Yeah, Don McLean, “American Pie,” what a song that is. A jester? Sure, the jester writes songs like “Masters of War,” “A Hard Rain’s A-Gonna Fall,” “It’s Alright, Ma” – some jester. I have to think he’s talking about somebody else. Ask him.

This would appear to run counter to everything I’ve just said, but I don’t think it does. To say somebody is funny is very different from saying somebody’s a jester. A jester is somebody who uses humor for a particular purpose, and that purpose is flattery. A jester tries to ingratiate himself with his supposed societal superiors by playing the fool. Well, it goes without saying but Bob Dylan is nobody’s fool. One of the reasons Dylan doesn’t get the credit he deserves for his sense of humor is because it’s wholly his own. His objective with his jokes is to amuse himself, which is part of his larger mission to stay true to himself. If other people get what he’s putting down, comedically or otherwise, that’s great. But as he told Denise Worrell in 1985, he’s not gonna go out of his way to say “This is funny.” People are either gonna laugh or they’re not. And he’s good with it either way.

All right, there are many more avenues I’d love to wander aimlessly down before eventually passing out, but in the interest of time I gotta get to the big finish. Why does any of this matter? Here’s why I think it matters, or at least this is why I think it’s worth caring about, and you can decide whether you think it’s worth caring about too. I’m a Bob Dylan fan, as I suspect most people in this room are. It’s a heck of a conference to come to if you aren’t. Although I suppose everybody’s gotta be somewhere.

As a Bob Dylan fan, my interest is in expanding the Dylan fandom. My interest is in ensuring that interest in Bob Dylan doesn’t die when he dies, or when we die. And the only way to ensure that is to bring new people into the fold. How do we do that? Two words: Timothée Chalamet.

I think that’ll help. But the way to do it, the real way to do it, the only way to do it – is to meet people where they are. To not put up walls. There’s a peculiar impulse in society today that says: “If somebody doesn’t like something as much as I do, I’d rather they didn’t like it at all. If somebody doesn’t know as much about something as I do, I’d rather they knew nothing.” And that is death.

There’s nothing wrong with serious people doing serious scholarship as it relates to Bob Dylan – I love it. I thank everybody doing that work. I think I’ve proven that it is not work I’m capable of doing. But I also think there’s space for sillier stuff. And I think that it is through some of this sillier stuff that we can welcome in new fans. People for whom Bob Dylan can feel like homework; people for whom Dylan can seem like a remnant of a bygone era. My experience has been that if you show these people that Bob Dylan is not only one of the most profound, important artists of his time, but that he is also hilarious, both in his work and just as a dude – you can connect Dylan with people who otherwise would pass him by. And then from there those people can drill down deeper if they want. Or they can just chill out and have fun on the surface. Whatever works.

I hope this worked. Thanks, everybody.