The 10 Most ‘Confounding’ Moments of Bob Dylan’s Career

When Bob Dylan accepted the 2015 MusiCares Person of the Year Award, he eschewed the quick, baffling remarks he often makes during such honors and spoke for 30 minutes, seemingly from the heart. He touched upon his unpredictable persona, saying:

“Critics have said that I’ve made a career out of confounding expectations. Really? Because that’s all I do? That’s how I think about it. Confounding expectations. Like I stay up late at night thinking about how to do it. ‘What do you do for a living, man?’ ‘Oh, I confound expectations.’ You’re going to get a job, the man says, ‘What do you do?’ ‘Oh, confound expectations.’ And the man says, ‘Well, we already have that spot filled. Call us back. Or don’t call us, we’ll call you.’ Confounding expectations. I don’t even know what that means or who has time for it.”

But while the way many of us read Dylan may be inadvertent, that doesn’t make it any less true. Rough and Rowdy Ways, Dylan’s first album of new material in eight years, is upon us. If Britain’s left-leaning Guardian and conservative Financial Times (read only by monocle-sporting gentlemen in dark oak private dining clubs) can both award something five-out-of-five stars, surely it’s got something. 

Three of its tracks have already been released. They include a spooky blues number, a 17-minute, melody-resistant elegy for John F. Kennedy and a ballad containing the lines, “I’m just like Anne Frank, like Indiana Jones / And them British bad boys, The Rolling Stones.” The only thing we should expect from the full album is not to expect anything.

In the meantime, to celebrate he who most confounds our expectations, here are 10 “Wait, what?” moments from Dylan — really, little more than the tip of the iceberg. And this list doesn’t even include “going electric at Newport”; telling Time Magazine he’s just as good of a singer as Caruso; permitting a hazy biopic of himself in which he is played, in part, by Cate Blanchett; or winning the Nobel Prize and not responding for two weeks. This is all far weirder.

The Tom Paine Speech (1963)

In December 1963, the 22-year-old Dylan received an award by the Emergency Civil Liberties Committee (ECLC) in New York. While some of his work was already on the vituperative side (“Masters of War,” “The Lonesome Death of Hattie Carroll”) no one was expecting him to get up on the stage to condemn anyone old enough to lose their hair, complain that the African Americans who spoke at the March on Washington didn’t look like his friends because “my friends don’t have to wear suits,” tell everyone to go to Cuba and, just weeks after the Kennedy assassination, say, “I saw some of myself in him” — the him being Lee Harvey Oswald. 

It did not go over well.

Dylan sent a letter (entitled “A Message”) to the ECLC shortly thereafter that is somewhere between an apology and an avant-garde work of poetry foreshadowing the similarly all-lowercase liner notes he’d publish on Bringing It All Back Home.

Woodstock No-Show (1969)

Part of the reason the “Woodstock Music & Art Fair’s Aquarian Exposition: 3 Days of Peace & Music” concert was overrun to the point of needing to shut down the New York State Throughway was due to a raging rumor that Bob Dylan was going to be there.

I mean — how could he not? The “voice of the generation” lived up there, unless you were one of the conspiracy nuts who believed he died in his motorcycle crash and the golden-toned voice on his newly released Nashville Skyline was actually someone else, man! No, what many believed (and what was partially true) was that he was still hanging out in a basement with his 1966 touring band, recording new songs. “If you don’t believe me, explain that muddy record in the plain white sleeve we heard at that party!” (Said record, Great White Wonder, being the first commonly traded bootleg, featuring material later known as The Basement Tapes.) He was for sure going to be there and blow everyone’s minds with a whole new sound.

Despite living a short drive away, Dylan turned down the offer and instead went to the Isle of Wight Festival in the U.K., his first public performance in over three years.

Christian Bob (1979 to 1981)

Bob Dylan’s real name, as you probably know, is Robert Zimmerman. He was raised Jewish, had his bar mitzvah and went to a Jewish summer camp. When he came on the scene, he didn’t exactly hide this, but he didn’t go out of his way to tell people, either. 

He later recorded three gospel-inspired albums: Slow Train Coming, Saved and Shot of Love (Saved kinda stinks, but the other two are terrific.) Was Bob Dylan really a born-again Christian, or was this an act? Interviews from before, during and after point in multiple directions. (He was also in a relationship with one of his backup singers, Clydie King, before marrying another, Carolyn Dennis). 

Either way, concerts from this period are a hoot, because he’d stop to give a sermon, which inevitably got the crowd heckling. “You want rock n’ roll, you can go see KISS!” is one of the better ones. 

It’s Hell Time, Mannnnnn (1986)

Bob Dylan has exploited cinema since the first days of his career. D.A. Pennebaker’s Don’t Look Back did a lot to cement his reputation as a genius (as did getting his early songs covered by more palatable acts like Peter, Paul & Mary, Sam Cooke, Sonny & Cher and The Turtles). The first time Dylan acted in a movie, as “Alias” in Sam Peckinpah’s Pat Garrett and Billy The Kid, it worked out for all involved. (“Beans!”) Plus it led to one of the great soundtrack albums.

But there were a lot of misfires. Most famous was the debacle of Renaldo & Clara, an inscrutable road movie directed by Dylan himself during the Rolling Thunder Revue tour. Much of this footage has recently been salvaged into a Martin Scorsese (quasi-) documentary, but for decades, this was something of a Holy Grail for fans who would finally get their hands on it, then feel tremendously disappointed. In 1987 came Hearts of Fire, from Return of the Jedi director Richard Marquand, in which Dylan was an elder statesman rock n’ roller entangled with young musicians played by Fiona and Rupert Everett. This whiff kept Dylan away from cameras for a long time, minus a super quick cameo as a welder in the 1990 film Catchfire, directed by Dennis Hopper, who then took his name off the project.

But the weirdest Dylan-at-the-movies moment came in 1986, when he offered up the title song for a movie called Band of the Hand. Dylan didn’t do this sort of thing often, though I am sure he had opportunities. (His 2000 track “Things Have Changed” for the film Wonder Boys won him an Oscar on his first try.) 

Band of the Hand was directed by Paul Michael Glaser, aka Starsky from Starsky & Hutch. He later made The Running Man and Kazaam. The film is basically about a halfway house of at-risk Miami youth who eventually clean up crime off the streets. The film has scenes of Outward Bound team-building and urban combat, and stars Laurence Fishburne, James Remar and Lauren Holly as the baddies, with Stephen Lang as the ex-Marine leading the juvies to righteous revenge. Among them, a young John Cameron Mitchell as a dangerous psycho. It’s unreal, and Dylan’s jangly blues (with The Heartbreakers, of “Tom Petty and” fame backing him) is constantly on the soundtrack.

Let Us Rejoice (1989)

Okay, let’s talk about Dylan’s religion again. 

Dylan has the reputation of being a scholar and a seeker, somehow tapped in to all cultures and many times lost. But what does he believe, man? We don’t know. We do know, however, that his daughter Maria married the Jewish musician Peter Himmelman in 1988, and that may have triggered something.

In 1989, Dylan, Himmelman and Harry Dean Stanton, who is not Jewish, appeared on a Chabad telethon and sang “Hava Nagila.” (Chabad is one of the branches of Orthodox Jewry. They are the most worldly of the extremely devout Jews, and the only ones who actively proselytize their co-religionists.) 

The video is something you need to see.

(Of note: in 1963, Dylan recorded a 53-second goof of the same traditional Jewish tune. It didn’t get an official release until 1991.)

So was Dylan now an Orthodox Jew? I don’t really know. But as recently as 2016 he was still hanging around Crown Heights to chat with the chief Chabad rabbi.

Masked & Anonymous (2003)

No feature film from my adult years has been dispatched to the memory hole quite like this one. Watch this trailer, then once you’ve stopped shouting, “Why have I never heard of this?!?” rent it on Amazon. (And it’s directed by Larry Charles, though under a pseudonym!) It’s not super fantastic or anything, but anyone with a passing interest in weirdness needs to see it. 

Shocking Revelations of Normalcy (2004)

Dylan’s long-awaited memoir, Chronicles, Volume One, is exactly what you’d expect from someone who confounds expectations. There’s a lot in there about his early years, being a young folkie hanging around Greenwich Village and learning from people like Dave Van Ronk. Then it blazes past all of his famous stuff to talk about the recording of the 1970 album New Morning. Then it really blazes past more stuff to sink its teeth into Dylan’s collaboration with Daniel Lanois on his terrific 1989 album Oh Mercy. 

What’s great about this section is he lets down the facade. He knows the albums he was putting out around this time period (Empire Burlesque, Knocked Out Loaded, Down in the Groove) may have one good track on them, but the rest kinda stink. Even though Dylan talks so much in interviews (and would later host 101 episodes of Theme Time Hour Radio for XM/Sirius Radio) he’s rarely ever illuminating about his own work.

Most fascinating, though, is how he writes about being a family man. In Chronicles, Volume One he discusses his 12-year marriage to Sara Dylan in ways that make pointless the longstanding hunt for clues many fans did with Blood on the Tracks. He writes about splitting New York City for upstate to raise his kids. He talks about how nuts it was that people like self-described “Dylanologists” like A.J. Weberman would root through his trash to gain insight into his lyrics. 

The biggest revelation in this book is just how much Bob Dylan yearned to be normal. 

Long Branch Bust (2009)

In summer of 2009, Dylan’s “Never-Ending Tour” swept through North America, with Willie Nelson and John Mellencamp joining the show. On July 21st they were in Pawtucket, Rhode Island and on July 24th they were in Aberdeen, Maryland. In between they hit Lakewood, New Jersey, and during the off-hours, the entourage camped at the Ocean Place Resort in Long Branch. (It’s nice; I’ve had brunch there.)

It was a rainy night, however, so swimming in the Atlantic wasn’t in the cards. As such, Dylan, wearing two raincoats, started wandering around the neighborhood and looking into windows. (One house had a For Sale sign on it.) Looking like a vagrant, somebody called the cops. When the world famous singer had no ID but said he was Bob Dylan, comedy ensued. He was given a lift back to the hotel by a disbelieving police officer, but the best part of the story is how he asked to be driven back to the strange house once his identity was confirmed.

New Jersey factoid! Although it’s highly unlikely, the house Dylan could have been looking at was the one Bruce Springsteen was living in when he wrote “Born to Run.” It is only 1.7 miles away from the hotel.

Dear Watson (2016)

Many have joked about Dylan’s 2004 ad for Victoria’s Secret. 

I can’t decide if I like Slate’s headline (“Tangled Up In Boobs”) or the Telegraph’s (“Hey Mr. Lingerie Man”) better, but who can blame him for selling out for such an intoxicating product? (Besides, he warned us that he would shill for panties back in 1965.)

But heady, hazy Venice-shot prurience is one thing. Borscht Belt schtick with an IBM computer is another. This commercial is so embarrassing that it actually kinda rules.

Tripling Down (2017)

Down & Dirty Ways is Dylan’s first album of new material in eight years, but he’s hardly been doing nothing. Apart from the “Never-Ending Tour” that began in 1988, he’s been in the studio with his live band making a slew of recordings. In 2015 he released Shadows in the Night, an album entirely of Great American Songbook standards that had previously been sung by Frank Sinatra. 

Though surprised, fans dug it. (I mean, he’d also released a Christmas album in 2009.) Shadows in the Night was followed-up by 2016’s Fallen Angels. More standards. (This time not just Sinatra tunes.)

The following year, he did it again, but a trilogy just wasn’t enough. The third album, Triplicate, was a triple-album. Three complete CDs (for those out there who still buy CDs) of 10 songs each written by the likes of Jimmy Van Heusen, Harold Arlen and Richard Rodgers. 

It’s all terrific, but it’s also a case of a fanbase eventually crying Uncle. Everyone is looking forward to Rough & Rowdy Ways. 

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Jordan Hoffman

Jordan Hoffman is a writer and film critic whose work has appeared in The Guardian, Vanity Fair and the New York Daily News.