Bob Dylan in Love

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From the beginning, Bob Dylan's music was fueled by desire. (In 1978, he described his early inspirations to Playboy: "The first song I wrote was a song to Brigitte Bardot… I don't recall too much of it. It had only one chord.")

Dylan's thirty-fifth album, Tempest, comes out today. His love life has been almost as tumultuous as his musical career; in tribute, we're taking a look back at some of his most important relationships and the songs they inspired.

Dylan's first major relationship was with Suze Rotolo, a young artist and daughter of radicals living in Greenwich Village. The musician was instantly smitten, later writing, "Right from the start I couldn't take my eyes off her. She was the most erotic thing I'd ever seen… The air was suddenly filled with banana leaves. We started talking and my head started to spin."

Dylan charmed Rotolo, who remembered him as "funny, engaging and persistent." They quickly moved in together, against the wishes of her parents. In light of the guarded persona he developed later, it's striking to see his openness with her in the many pictures of them together. (Even the fact that many pictures exist is striking, actually.) But his mystique was already in play; Rotolo didn't learn his real name until his draft card fell out of his wallet.

The most famous of these photos is the cover of The Freewheelin' Bob Dylan, which also contains several songs about Rotolo, including "Don't Think Twice It's All Right," possibly the greatest breakup song of the 1960s.

"Don't Think Twice It's All Right"


Dylan's relationship with Rotolo was passionate and fraught. A self-realized woman, she influenced Dylan as much as he influenced her, but was troubled by his growing fame and the narcissism that stoked it. "Bob was charismatic: he was a beacon, a lighthouse, he was also a black hole. He required committed backup and protection I was unable to provide consistently, probably because I needed them myself," she remembered. "As his girlfriend, I disappeared and became a nonentity. Even if he didn't see me that way, that's what happened." Against Dylan's wishes, Rotolo left New York in 1962 to study in Italy. Dylan wrote the anguished "Boots of Spanish Leather" about her departure.

"Boots of Spanish Leather"


Rotolo returned having read a memoir by Pablo Picasso's muse Françoise Gilot, and being alarmed by the resonances she recognized with Dylan. Still, they stayed together until 1964. Dylan describes their breakup in "Ballad in Plain D," in a raw and injured lyric he would later regret, saying, "I must have been a real schmuck to write that."

"Ballad in Plain D"


Unbeknownst to Rotolo, Dylan was already seeing Joan Baez, who he'd met in 1962. They played together at the March on Washington in 1963, and she was instrumental in popularizing his work in the folk scene. Baez suspected that Dylan's mystical love song "Visions of Johanna" was about her, though Dylan never confirmed it.

"Visions of Johanna"



Dylan and Baez had an acrimonious breakup in 1965. One song Baez might've been less happy to inspire was "Positively 4th St.," a scathing kiss-off to the Greenwich Village folk scene.

"Positively 4th St."


Around this time, Dylan was womanizing up a storm. (All in the name of art, of course.) One of his many flings was British soul singer Dana Gillespie (left), who recalled, "I guess he was juggling women, like most musicians." Gillespie remembered an episode in which Dylan borrowed her pants and left her in his hotel room: "I was stuck in my underwear because he had taken my trousers. He could fit into mine, but I couldn't fit into his. I had to sit in the hotel waiting for him to come back. He said, ‘I'll only be a few hours.' It was about fifteen hours before he came back." But she liked him anyway: "He's amusing, he's spiritual. Women prefer to be seduced by a brain than bullock. Brains go a hell of a long way."

One of Dylan's more high-profile connections in this period was with Edie Sedgwick (right). Sedgwick was infatuated with Dylan, while Dylan was leery of the world of celebrity represented by Andy Warhol and warned Sedgwick away away from her association with the artist. While Dylan later said that his relationship with Sedgwick had not been sexual, his hit "Just Like a Woman" was widely interpreted to be about her. With its references to "fog, amphetamine and pearls," it does seem to evoke the doomed socialite. "Leopard-Skin Pill-Box Hat," a satirical snip at a fashionista, is also said to have been inspired by Sedgwick.

"Just Like a Woman"


Sedgwick's infatuation with Dylan was apparently somewhat deflated when she discovered that he'd secretly married Sara Lownds, a fashion model, stage actress, and Playboy bunny. Dylan had started seeing Lownds while still with Baez, and quickly fell in love. He wrote many songs about her, of which the most famous is probably "Sad-Eyed Lady of the Lowlands."

"Sad-Eyed Lady of the Lowlands."


Dylan and Sara had four children together; by most accounts, he was deeply reliant on her. But the relationship soured in the mid-'70s when Dylan began taking art classes. His teacher's methods had a profound effect on Dylan, who later said, "I went home after that first day and my wife never did understand me ever since that day. That's when our marriage started breaking up. She never knew what I was talking about, what I was thinking about, and I couldn't possibly explain it." Dylan's album Blood on the Tracks seems to describe this estrangement; Dylan has denied it, but his and Sara's son Jakob later told a biographer, "Those songs are my parents talking."

"Tangled Up In Blue"


If Dylan's philosophical change after art class was the emotional explanation, the practical explanation was a little clearer: Sara apparently came downstairs one day to find Dylan with another woman. When she filed for divorce and hired a therapist to help their children with the separation, Dylan slept with the therapist. In the midst of this ugliness and bad behavior, he also wrote "Sara," which finds him pleading for forgiveness, singing, "Loving you is the one thing I'll never regret."



Dylan's love life since his first divorce has been secretive, to say the least. In 1986, he married Carolyn Dennis, apparently one of many black backup singers he had affairs with. (Another, Clydie King, stands next to him in the picture above.) Dylan and Dennis divorced in 1992, but Dylan managed to keep this marriage a secret from the press for several more years. Dennis and Dylan promised their children privacy, with Dennis saying, "I have three children, but I'm not going to say which ones are Bob Dylan's… Bob Dylan has eight or nine children. We're not trading on that." Another lover, Susan Ross, was with Dylan for some dozen years starting in the mid-'80s. According to Ross, Dylan was charming and warm, but also essentially incapable of intimacy. Ross says she once asked him why they couldn't live together. His reply explains a lot about both his romantic history and his astonishing musical accomplishment: "Because I can barely live with myself."

"Most of the Time"


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