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Slices of NYC music history go under the hammer —including Madonna and Bob Dylan’s first recordings

Rare items tied to the New York City music scene are on the auction block at Guernsey’s and will tomorrow land in the hands of lucky collectors.

Personal pieces range from autographed musical instruments to history-making recordings and snapshots taken on a first date with Madonna.

One things you won’t see are love letters written by the Material Girl. Former boyfriend Dan Gilroy planned on selling the sweet notes which conveyed her missing New York while on a trip to Paris and, as Gilroy put it to The Post, “little notes about how she went for a walk with Grey Boy the cat.”

Dan Gilroy lived with Madonna and watched her musical chops develop. Now he’s selling the instruments she learned on. Getty Images

But Madonna put the kibosh on those being sold – Madge insisted that “she’s very protective of her writing” – and offered to sign the instruments if Gilroy, who played with her in her first NYC band, the Breakfast Club, agreed to turn over the sweet notes.

“I thought they were beautiful and poetic,” Gilroy said. “They were wonderful, but I gave them back.”

Here are some of the things you can bid on when the auction begins at 2 p.m. Wednesday.

Photographs of Madonna

Estimate: Various lots range from $800 to $5,000

It was 1979 when Dan Gilroy met Madonna at a party. “We hung out that night; then she called me the next morning and said, ‘Let’s go to the Cloisters,’” Gilroy told The Post. “So, we took a bus up there.”

Gilroy had his camera with him and Madonna proved to be a game subject. “She did all kinds of funny things,” he remembered of their first date, which is captured in the snaps for sale. “She pretended to pray to a statue, got on line behind a bunch of nuns, laid down on the bus seat and kicked her legs in the air.”

Told that Madonna sounds like a lot of fun, Gilroy added, “She wanted to be noticed and was very expressive. In fact, after she made it, Madonna said to me, ‘I used to spend all my time trying to be noticed. Now I spend all my time hiding.’”

Dan Gilroy snapped photos of a young Madonna. Now they are up for sale. Courtesy of Guernsey’s

Madonna’s Drum Set

Estimate: $30,000 to $40,000

Madonna and Gilroy lived in a former synagogue in the Corona neighborhood of Queens. Gilroy, who was partnered in a small fashion design company, happened to have a drum set he bought from a friend for $500.

“She learned very quickly,” said Gilroy. “Since she had a dancer background, she picked up the beats in no time. She played on stage at CBGB in our band Breakfast Club. Then she’d come off the drums and sing a couple songs. The audience reacted very well.”

Madonna mastered the drums quickly. Dan Gilroy attributes it to her background as a dancer. Guernseyâs / SWNS

Madonna’s First Guitar

Estimate: $50,000 to $75,000

When Madonna first got with Gilroy, she was a six-string neophyte. That changed when she started strumming on his acoustic guitar

“I bought it for $125 and it was what I used to play at home,” said Gilroy. “She wanted to write songs; so I showed Madonna a few bar chords and she began writing. An early one, “Daniel,” was about me.”

This is the guitar on which Madonna first learned to play. She signed it ahead of the auction. Emmy Park for NY Post
Alongside the guitars is also a small portable amp, which Gilroy says they used during their first public performance Emmy Park for NY Post

Bob Dylan’s Master Tape for “Bob Dylan”

Estimate: $300,000 to $500,000

Stephen Handschu, a sculptor who was born blind, moved from Chicago to New York City. He happened to be friends with a security guard who worked at Columbia Records, the label for which an unknown musician named Bob Dylan was signed to record his first album.

Tapes from the recording session were poised to be incinerated and were believed to have been erased. Seeing Dylan’s name on the tape box, the security guard asked if he could have them. A supervisor told him it would be fine.

Master tapes for Bob Dylan’s first album were thought to be blank. Their current owner, Stephen Handschu found out otherwise. Emmy Park for NY Post

Somehow, those tapes wound up in the hands of Handschu who, for decades thought they were blank. “My family laughed at me as I carried them from one move to the next,” he told The Post, adding that, in 2008, while volunteering to help disabled voters put down audio ballots, he came across a reel-to-reel machine and asked the engineer if he would play the tape. “He put them on, and, lo and behold, the tapes are pristine and the master recording of Dylan’s first album is on there.”

While Handschu welcomes the money (a portion of which will be donated to an education organization for the blind called EYE Learn), what’s most important to him, he said, “is that there is an object in my possession that was integral to the changing of American music.”

Bob Dylan wrote one of his signature songs, “Visions of Johanna,” while living in the Chelsea Hotel. Redferns

Chelsea Hotel Sign

Estimate: $50,000 to $75,000 for the word Chelsea; $5,000 to $10,000 for individual letters

The Chelsea Hotel was a haunt for musicians of every stripe.

It provided inspiration for Bob Dylan, soon to be played by Timothée Chalamet in a biopic, and Leonard Cohen. Dylan wrote the elegiac “Visions of Johanna” while ensconced there. Cohen penned a song called “Chelsea Hotel No. 2,” about an affair he had with Janis Joplin at the Chelsea. It’s where Patti Smith recited poetry while Sandy Daley shot footage of Robert Mapplethorpe having his nipple pierced. It’s also where punk Sid Vicious is believed to have killed girlfriend Nancy Spungen in a heroin-fuelled rage.

Now the sign that was a homing light for the people who stayed there can be purchased letter by letter. High rollers might go for the entire word Chelsea. “The sign was made in neon right after World War II,” Arlan Ettinger, president of Guernseys, told The Post. “It’s known around the world and is one of the first things you see when you watch the opening credits of ‘Saturday Night Live.’”

The original neon Chelsea lettering from the hotel, which was created shortly after World War 2 Emmy Park for NY Post
The Chelsea Hotel’s iconic sign is being sold off letter by letter. Christopher Sadowski
Patti Smith read poems in a Chelsea Hotel room as Robert Mapplethorpe had his nipple piereced. Getty Images

Madonna’s Early Recordings

Estimate: $1,000 to $10,000 for an assortment of lots

Like all striving musicians, Madonna and Gilroy made their share of home recordings.

“Some of them are our rehearsal tapes,” said Gilroy.

Asked if he’s surprised Madonna does not mind him selling off her early musical efforts, Gilroy explained, “The songs are really fabulous for first outings. They are just so good.”

As for his favorite of the bunch, Gilroy referenced “A Letter to Daddy.” In describing it, he said, “She is expressing her disappointment in her father’s disappointment at her leaving home at age 19 and coming to New York with no money. You can imagine how afraid he was of the whole thing.”

Early Madonna recording contain at least one song about her father, and bandmate Dan Gilroy describes them as “really fabulous for first outings.” Emmy Park for NY Post
Another tape containing Madonna’s earliest recordings when she was in Breakfast Club and played the drums, as well as sung Emmy Park for NY Post
Madonnas’s first public musical performance featrured this guitar, which she has signed. Emmy Park for NY Post

Madonna’s Electric Guitar

Estimate: $100,000 to $150,000

Gilroy’s used electric Rickenbacker, purchased for $150, is the first instrument with which Madonna performed publicly as a musician.

As he remembers it, they dressed in white, walked through the streets of Manhattan and played. “I had a [portable, battery powered] amplifier strapped to me,” he said. “After a crowd formed around us, a cop came out and told us to beat it. We walked away from the crowd but didn’t stop playing.”

Years later, having written the kinds of songs that would one day make her famous, Gilroy remembered getting together with Madonna so they could make music together. She played the electric guitar, Gilroy took to the drums and they swung through her tunes.

“It hit me,” he remembered of the jam session, “this woman is going to be big.”

This post was originally posted by NYPost

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Written by Michael Kaplan

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