What Bob Dylan Wrote in His High School Love Letters

A collection of notes from the musician to his girlfriend sold for nearly $670,000 at auction

Bob Dylan in 1974
Before changing his name to Bob Dylan, the popular singer-songwriter was Robert Zimmerman. Bettmann / Getty Images

Before becoming an international superstar, Bob Dylan was just a normal teenager named Robert Zimmerman growing up in the Midwest. And, like many teens, he spent much of his time penning long, romantic missives to his high school sweetheart.

Now, fans and scholars will also soon get to enjoy the renowned singer-songwriter’s heartfelt sentiments. The Livraria Lello bookshop in Porto, Portugal, bought a trove of the musician’s handwritten love letters for nearly $670,000 at auction last week.

The popular shop, which calls itself “the world’s most beautiful bookshop,” plans to make the letters available for study, reports the Associated Press.

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The collection includes 42 letters Dylan, then Zimmerman, wrote to his high school sweetie, Barbara Ann Hewitt, while the two were in school in Hibbing, Minnesota. All told, the “unprecedented archive” features 150 pages of text, according to Boston-based RR Auction, which offered up the documents as part of its recent “Marvels of Modern Music” sale.

The letters, penned between 1957 and 1959, are like a time-capsule from the late ’50s. In them, Zimmerman wrote about popular clothing trends and cars of the time, as well as the music he was listening to. He included snippets of poetry, discussed plans for entering the Hibbing High talent show—and, of course, “[professed] his never-ending affection,” per the auction house.

The teen even shared with Hewitt his plan to change his name and one day sell a million records. He made both of those goals a reality: Dylan, who is 81, has sold an estimated 125 million records worldwide.

Bob Dylan signature
Dylan, then Zimmerman, wrote about trends and culture of the late 1950s. Courtesy of RR Auction

Dylan was born in 1941 in Duluth, Minnesota, but grew up in Hibbing, a small mining town in the northeast part of the state where his father co-owned a furniture and appliance store. Hewitt, meanwhile, moved to Hibbing with her family as a teenager and met Dylan in history class. They had their first date on New Year’s Eve in 1957 and, based on the letters, continued dating through the end of 1959. After Hewitt died in 2020, her daughter found the sweet notes and decided to auction them off.

The auction also sold other pieces of Dylan memorabilia, including signed photographs, handwritten poems, song lyrics and more.

Bob Dylan's love letters
The collection includes 42 letters totaling 150 pages of handwritten text. Courtesy of RR Auction

Dylan got his first guitar at age 14 and played in several bands throughout high school. While studying at the University of Minnesota, he changed his name and began performing in coffee shops. He moved to New York City and released his first album in 1962.

His career skyrocketed from there. Today, Dylan is regarded as the “Shakespeare of his generation,” as Encyclopedia Britannica puts it. He’s penned more than 500 songs recorded by more than 2,000 musicians, and he received the Nobel Prize for Literature in 2016.

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