Bob Dylan’s Teenage Love Letters Go to Auction

A collection of love letters written by Bob Dylan in his teenage years has gone up for auction, with bidding starting at a cool $250,000.

The 42 handwritten notes, totaling 150 pages and including a valentine, were sent to Barbara Ann Hewitt between 1958 and 1959, when Dylan was roughly 17-18 years old and living in Hibbing, Minn. RR Auctions, the sale conductor, did not reveal the precise contents but offered a hint at what the letters contain.

“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,” the lot description reads. “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.”

The couple met in their high school history class. “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,” RR Auctions reported. “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.”

“This archive is one of the most culturally important of the 20th century we have ever offered,” said RR Auctions vice president Bobby Livingston (via the Associated Press). He described the letters as as a “first-person account of Dylan’s formative years,” adding, “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.”

One of the last letters illustrates the end of the relationship, with Dylan asking Hewitt to return the photos he’d sent her. Hewitt married in the ‘70s but divorced after seven years. She remained unmarried up until her death in 2020.

Hewitt’s daughter told Livingston that Dylan called his former lover in the ’60s and invited her to attend one of his shows, but she turned him down. Livingston also speculated that Hewitt, a redhead, was immortalized in some of Dylan’s lyrics, perhaps in the opening lines of 1975’s “Tangled Up in Blue”: “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.”

The lot will be sold on Nov. 17. Dylan retains copyright of the lyrics and poetry he wrote to Hewitt.

Listen to Bob Dylan’s ‘Tangled Up in Blue’

Bob Dylan Albums Ranked

Not so surprisingly, Bob Dylan’s recording career has lots of ups and downs. That’s bound to happen when you stick around for more than 50 years and release three dozen albums during that time.

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