Bob Dylan’s Teenage Love Letters To Be Sold At Auction


A collection of love letters that were written by Bob Dylan during his teenage years are expected to make a splash at an auction next week.

The letters were sent by the singer when he was roughly 17-18 years old between 1958 and 1959.

At the time, Bob Dylan was courting a girl named Barbara Ann Hewitt. The singer was living in Hibbing, Minn at the time.

There are 42 handwritten notes in total, containing 150 pages overall, including a valentine.

Bob Dylan met Barbara Ann Hewitt during a high school history class, according to reports.

“never ending affection”

The auction sale is being conducted by RR Auctions, who have released the following description.

“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”, it reads.

They also added, “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”. 

On the pair’s romance, RR Auctions also added, “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”. 

Check out these letters here.

Elsewhere, RR Auctions’ vice president Bobby Livingston also described the letters as “first-person account of Dylan’s formative years”. 

“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”, he said.

‘Tangled Up In Blue’

Another letter included in the collection also covers the break up of this romance. In this letter, Bob Dylan asks for Hewitt to return some photographs he sent her.

Following the break up, Barbara Ann Hewitt got married in the 1960s. Her marriage ended after seven years. She passed away in 2020.

Hewitt’s daughter reportedly told Livingston that Bob Dylan had invited his former lover to attend on of his concerts in the 1960s, however she declined.

As her mother was a redhead, Hewitt’s daughter has always speculated that Bob Dylan’s track ‘Tangled Up In Blue’ may have been about Barbara.

The lyrics read, “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 collection will go under the hammer on November 17, with the bidding beginning at $250,000.

Earlier this month, a collection of essays was also released by Bob Dylan,‘The Philosophy Of Modern Song’. Chapters for the audiobook were read by Helen Mirren and Jeff Bridges. More on this here.