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The tragic story of Bob Dylan's favourite singer of all time

Bob Dylan is unquestionably one of the greatest artists of all time, the impact he has had on the musical landscape is immeasurable and he is rightly recognised as an icon. Dylan has been namechecked as an influence by legendary artists like The Beatles and The Rolling Stones but the freewheelin’ troubadour drew his influences from more obscure quarters. Instead, his favourite singer was far from a famous name and if it wasn’t for Dylan’s profile they would likely have been etched out of history.

Dylan cut his teeth going from coffee shop to coffee shop across New York’s legendary Greenwich Village, this scene was filled to the brim with talent and soon enough musicians like Dylan would graduate to the bigger stage. Tragically, this wasn’t to be the case for everybody and some artists weren’t destined to be the next Bob Dylan or Joni Mitchell. Some of the brightest singers that the scene had to offer would never quite make it and get the recognition that their talent warranted, including Dylan’s favourite Karen Dalton.

The singer had lived quite the coloured life before arriving at her own musical mecca in Greenwich Village. The singer had suffered two divorces by the age of 21 and it was clear from her music that Dalton had more than enough life experience to pour into her performances. It was this proposition which soon took the scene by storm.

It didn’t take Dalton long to become a vital pillar of Greenwich Village scene after her arrival in the early 1960s and she immediately gained the respect of her peers. Bob Dylan, on occasion, would back her up on the harmonica and she also played with other stalwarts of the scene including Fred Neil, Richard Tucker, and Tim Hardin. Dalton would go on to marry Tucker and they would often play together but playing by herself was something which she was reluctant to do, she was especially hesitant about performing her own songs in public.

In his 2004 memoir Chronicles: Volume One, Bob Dylan wrote, “My favourite singer was Karen Dalton. Karen had a voice like Billie Holiday and played guitar like Jimmy Reed, I sang with her a couple of times.” With praise like that from arguably the greatest of all time, why is Karen Dalton not a household name? Her story is drenched in sadness and her life was marred by addiction and crippling stage fright, something which stopped her from ever getting her career off the ground.

It would take until 1969 for her to release her debut album, It’s So Hard to Tell You Who’s Going to Love You the Best. The record wasn’t the result of Dalton suddenly gaining a shot of confidence, in fact, the album was only recorded because Fred Neil fooled her into believing the tape wasn’t rolling. The follow-up, In My Own Time, was recorded at Bearsville studio, near Woodstock in upstate New York, which was set up by Bob Dylans’s manager, Albert Grossman. 

Grossman tried his hardest to pull out all the stops for Dalton to make the record successful, including building an impressive team around her to make up for her phobia of songwriting. Despite this, the record still failed to be a commercial success and her last chance seemed to slip through her fingers. Producer Harvey Brooks told The Observer in 2007, “the fact that she wasn’t a writer meant that we really had to create something for her,” he says. “It was a lot of work, because her emotional personality had to be dealt with every step of the way. And respected.”

“It just didn’t work out for her. For some people it’s just like that; they give, but they don’t get. And it just broke her heart. After that, she couldn’t get her life together and in the music business you have to be able to promote your product. That album didn’t sell and nobody was gonna put the money up to make another,” Brooks added.

Dalton would fall deeper into the pits of addiction, become estranged from her family and, by the early 90s, she found herself living on the streets of New York. Her friend Friend Lacy J. Dalton helped send her to rehab in Texas in the early 1990s but her stay would only last a couple of days, Lacy wanted her to remain at the facility long enough to get her teeth fixed but what she didn’t realise was that the teeth problem was Karen’s way of getting codeine — which, sadly, is what she cared about more than getting clean.

She tragically succumbed to addiction by choosing to return to the streets of New York and passed away a year later in 1993, aged just 55. The cause of death still remains unclear, Brooks said: “From what I understand, she ran out of steam”. However, others say it was a drug overdose and it’s also claimed by her friend Peter Walker that she passed away from an AIDS-related illness that she had been suffering with for eight years. Dalton remains one of music’s saddest stories and question marks still remain about what could have been if she hadn’t suffered her addiction issues.

Listen to Dalton’s beautiful ‘Something On Your Mind’, below.