Love Letters Written by a Teenage Bob Dylan Go Up for Auction

A collection of love letters, lyrics, and poems written by Bob Dylan when he was a teenager will go up for auction on Nov. 17 by RR Auctions with bidding starting at $250,000.

The lot of letters, written to Barbara Ann Hewitt between 1958 and 1959 from Dylan, who was 17 or 18 years old at the time and still living in Hibbing, Minnesota, include 42 handwritten notes, totaling 150 pages, and a valentine.

The letters reveal a younger, and very motivated Dylan, who at one point asks Hewitt, who he first met in their high school history class, what she thinks about him changing his name (monikers like Little Willie and Elston are mentioned). He also talks about appearing on American Bandstand and one-day selling a million records.

“Wide-ranging in scope and content, the young Dylan reveals his dreams of changing his name and selling a million records, offers bits and pieces of poetry, and professes his never-ending affection,” reads the RR Auctions description of the lot. “He prepares for the Hibbing High talent show; invites Barbara to the Buddy Holly show in Duluth; speaks of singing, songwriting, and recording; comments on the cars and clothing of the late 1950s; and writes on the records he’s listening to.”

Another RR Auctions summary of the letters adds, “On New Year’s Eve, 1957, Barb and Bob had a date to a holiday-season party downstate, in the Twin Cities area, and they fell in love that night. January of 1958 saw the beginning of an epistolary correspondence that went on into 1959, and perhaps beyond. Barb’s letters to Bob may or may not survive.”

A later letter captures the end of Dylan and Hewitt’s relationship. In the letter, Dylan asks Hewitt to return the photographs he gave her. Hewitt was married in the 1970s and later divorced and remained unmarried until her death in 2020.

Hewitt’s daughter, who found the letters after her mother died, told RR Auctions that Dylan once called up her mother to invite her to one of his shows in California in the 1960s, but she declined. Bobby Livingston, vice president of RR Auctions also suggested that Hewitt, who was a redhead, may have been immortalized in some of Dylan’s songs, including “Tangled Up in Blue” from 1975—Early one morning, the sun was shining / I was laying in bed / Wondering if she’d changed it all / If her hair was still red.

“This archive is one of the most culturally important of the 20th century we have ever offered,” said Livingston. “They really give an insight into how he’s going to present himself. It shows that Dylan dreamed all this up, and it all came true. He foresaw it.”

The Barbara Hewitt Estate is the owner of the physical archive being auctioned, while Dylan retains the copyright of the unpublished writings, poems, and song fragments within the letters to Hewitt.

See photographs of the lot of letters written by Dylan to Hewitt HERE.

Photo by PL Gould/IMAGES/Getty Images