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Dylan, now 81, posted poetry and confessed his love to Barbara Ann Hewitt. Perhaps he also imagined his future success most impressively.

This September 2022 photo shows a personal collection of love letters written by Bob Dylan to his high school sweetheart in the late 1950s. A personal collection of love letters is put up for auction. Nikki Brickett / RR Auction / Estate of Barbara Hewitt by AP

A very personal collection of love letters in which teenage Bob Dylan tells his high school sweetheart that he intends to change his name and sell a million records will go on sale in Boston.

The Hibbing, Minnesota, a boy – still known then as Bob Zimmerman – wrote 42 letters totaling 150 pages to Barbara Ann Hewitt between 1957 and 1959. period in the life of the folk-rock icon about which little is known first hand.

“This archive is one of the most culturally important of the 20th century we have ever offered,” said RR Auction Executive Vice President Bobby Livingston, a huge Dylan fan.

The collection, including the rich Valentine’s Day card, is “the first person to describe Dylan’s youth,” he said.

Hewitt’s daughter found letters after her mother’s d*ath in 2020. Along with the original envelopes addressed with Dylan’s handwriting, they are offered as a single lot with an initial bid of $ 250,000. The auction ends on November 17th.

RR Auction does not publish the exact content of the letters in advance, but does address the timeless and universal problems of teenagers: clothes, cars and musical tastes, the auction house said.

Dylan, now 81, also published poetry and professed his love for Hewitt. Perhaps he also imagined his future success most impressively.

In one letter, he asks Hewitt for feedback on his name change (the letters mention Little Willie and Elston) and writes about selling a million records (in fact, he sold about 125 million) and performing on the American Bandstand in front of crowds of screaming girls.

“They really give a glimpse of how they’re going to present themselves,” said Livingston. “It shows that Dylan made it all up and it all came true – he predicted it.”

Unfortunately, like most teenage romances, it ended. In one of the last letters, the future Nobel Prize winner asks Hewitt to return the photos sent to her.

But it seems likely Dylan didn’t forget her. Hewitt’s daughter told RR Auction that Dylan called her mother in the late 1960s after he had achieved great success and asked her to come to California. She rejected him.

Hewitt was redheaded, and Livingston speculates that Dylan’s references to redheads or auburn women in some songs were Hewitt-inspired, including “Tangled Up in Blue” where he wonders in one line “was her hair still red”.

Apparently, Hewitt moved on. She married another Hibbing but divorced in the late 1970s after seven years and never remarried, as her daughter told the auction house.

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