My first memory of Bob Dylan is from a cassette that I borrowed from my father in 1985, when I was 13, and never returned. This was a tape a friend of his made that included at least two tracks from The Last Waltz, Dylan and The Band performing Forever Young and Baby Let Me Follow You Down. Dylan was one of my father’s musical heroes, but his taste ran toward the folk and protest songs of Dylan’s early years. He wouldn’t have been one of the fans booing Dylan for plugging in, but he wouldn’t have listened either, so he didn’t miss the stolen cassette with its electric guitars and drums. I listened to these couple of tracks in my bedroom and got goosebumps from Dylan’s voice on Forever Young. There was something in his delivery and the lyrics that was simultaneously melancholic and hopeful.

Dylan’s music holds a special place in my heart. With his narrative “I,” he sees and calls out the injustice of human hypocrisy, recognizes the pain and beauty of love, and sings of life and death. At the same time, he is only self-aware to a point and, especially when it comes to respecting women, he falls far short of the man I want him, and myself, to be. I know I will get in trouble with some male fans for saying that, but so be it. Like Dylan at his most defiant, I’m not here to please them.

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I saw Dylan in concert for the first time on July 4, 1986 at Rich Stadium in Buffalo. The show was part of Farm Aid and included The Dead and Tom Petty and the Heartbreakers. I was 14. I didn’t know much more of Dylan’s music than those couple tracks off that cassette. I’d probably heard his greatest hits album too. My father took me to the concert; just as Dylan was my father’s musical hero, the Grateful Dead were mine at the time.

My father and I started the concert very near the stage, close enough to see Dylan’s leather pants and to see the gospel singers backing songs I didn’t recognize. We soon made our way to the top of the stadium so we could see the 70,000+ crowd from that high-up vantage point. Dylan played Rainy Day Women and nearly everyone there sang along: “Everybody must get stoned!” To my teenage ears, it was near religious. I wished I could have taken a hit off the joint another concertgoer tried passing to my father and I at what felt like the top of the world.

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Throughout high school and college, I learned more about Dylan’s early folk and blues work. Along with Crosby, Stills, Nash, and Young’s So Far and Jefferson Airplane’s Surrealistic Pillow, Dylan’s eponymous first album was one of my first CDs.  Misty morning drives through upstate New York’s rolling hills with cassettes of Dylan’s first albums are some of my favorite memories of my college years. I especially remember a road trip to Montreal, my friend Jesse bursting into laughter when Dylan sings, “make love to Elizabeth Taylor / catch hell from Richard Burton” in I Shall Be Free. I laughed too, though I had only some vague idea of who Richard Burton was. I performed knowledge, like many young people do in the presence of peers they admire.

I was halfway through college when Dylan’s Bootleg Series, Vol 1-3 came out. Around that time I transferred to a new school where I met my friend Matt. We connected in a philosophy class one day when we became the default leaders of a discussion on Alfred North Whitehead’s Science and the Modern World. I asked him out for a beer, and we connected over humor, literature, and music—especially our love of Dylan. Matt was the first to play the Bootleg Series collection for me. We listened to and discussed Dylan the same way we read literature and philosophy, with the same rigor and joy. It fundamentally changed my relationship to Dylan and music generally to approach it as literature. It was always nascent in me to “read” music this way, but the conversations with Matt refined and legitimized a way of listening that I had thought was merely idiosyncratic to me until then.

We were especially drawn to Last Thoughts on Woody Guthrie, a poem included on the first Bootleg Series. I had very little idea who Woody Guthrie was, but Dylan communicates so much in these 7 minutes. It is a meditation on the ambiguities and surrealities of life and art, a treatise of sorts.

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I moved to Chicago in the mid-90s; Matt had moved there earlier for grad school. We reconnected and I remember how enthralled we were with Blood on the Tracks in those years. We’d listen to it and talk about it like a treasured work of literature, trying to glean biographical insights from the tangled metaphors and similes, marveling at the piercing harmonica of You’re Gonna Make Me Lonesome When You Go, admiring the turn in Idiot Wind when the narrator gets swept up by his own judging eye. I remember one late night, when we both should have been doing other things, hitting on the idea that the somewhat goofy Lily, Rosemary and the Jack of Hearts functioned as a kind of intermission music between two loosely defined acts, the first act a kind of performance of grief and denial and the second act one of forgiveness and acceptance.

For my birthday in 1997, a few of us, including Matt, went to see Dylan live at Pine Knob in Michigan. The concert was the first time I’d seen Dylan live since 1986 and he was at the top of his game, just a month and a half before Time Out of Mind was released. One of the best parts of the concert was getting to see his opening act, Ani DiFranco, for the first time. She had just released Living In Clip and performed songs as though her life depended on it. I thought she was just as Dylan described her, when he came out on stage: “The amazing Ani DiFranco!”

I have seen Dylan perform another half dozen times at least since 1997 and he has mostly been impressive live. The show that sticks out the most for me was at The Metro, a small club in Chicago, just after the release of Time Out of Mind. At that show, the guy next to me started shouting “We love you Bobby D.!” before the opening act had even begun. He was not a literary fan, but a partier. He was drunk and loud and kept trying to light up a joint, which the security guard on the stage kept warning him not to do. At some point, the beers caught up with him. Instead of making the trip to the restroom, which would no doubt have cost him his prime real estate steps from the stage, he pissed in one of his empty beer cups and placed it between his feet. Then he tried lighting his joint again. The bouncer, with a swipe of his index finger across his throat, indicated that if he tried again, he’d be ejected from the concert. Ten minutes later, the lover of Bobby D. was being carried out by his belt and the collar of his shirt and I stood in his urine for the rest of the concert. I tried to laugh about it and think of it as the perfect metaphor for postmodernist listening to Dylan’s music – the highbrow and the profane together in one experience.

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In the last decade or so, Dylan’s music has become complicated for me. I still love it and listen regularly. His melodies and many turns of phrase continue to move me. At the same time, I cringe at the fact that it has taken having a daughter to uncover for me what was always in full view: the times when Dylan dismisses women, the way his female leads are often less than fully realized. And some of his more recent lyrics like “some young lazy slut has charmed away my brains” do not land well on my ear at all.

I recognize that this places me in the rightly ridiculed category of men who don’t realize women are people until they have a daughter. But I do see now how women in Dylan’s songs are mainly important to the extent they reflect the best of him; they are belittled when they reject him or reflect back less-than-flattering images of himself. I’m not ready to “cancel” Dylan, but I do want to be able to expect more from him and from myself.

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I’m still with Dylan as he enters his 9^th decade on earth. He doesn’t seem to be winding down anytime soon. Rough and Rowdy Ways holds up against much of his later catalog. I find Murder Most Foul insufferable, but there are many who think it is one of his greatest songs in years. Perhaps I am one of the booing fans when Dylan does the 2020 equivalent of plugging in. But, despite it all, I am still a fan.