See Amy Winehouse, Lady Gaga’s Letters to Tony Bennett

As anyone who’s seen the Amy Winehouse documentary Amy may recall, the troubled singer was initially rattled when she and Tony Bennett were cutting a duet in a recording studio, mere months before her death. “Amy was freaking out and the tape was running,” recalls Danny Bennett, who was managing his father. “She was ready to flee at any moment.”

What we don’t see in the doc is the moment when Danny Bennett approached Winehouse and, at his father’s request, asked her to sign a copy of the sheet music they used to sing the standard “Body and Soul.” “Happy 85th /You handsome legend you,” Winehouse wrote. “Your biggest fan. (My dad is literally much bigger in person than me though), Amy XX.”

For somewhere between $1,000 and $1,500 (though possibly much more), that collectible could soon be in the hands of a Bennett or Winehouse fan. Along with hundreds of other items, it will be part of an upcoming auction, “Tony Bennett: A Life Well Lived,” of items from Bennett’s personal archives.

After Bennett’s death last July at 96, Danny Bennett realized the extent of memorabilia his father had left behind in a storage space in New York. “Tony never had any awards in his house,” Danny tells Rolling Stone. “We never grew up that way. They were all in my office. Tony would find them very distracting.” The archives included microphones from his live shows, letters from presidents and celebrities, paintings Bennett both collected and created himself, and even a San Francisco cable-car bell given to him after he’d supported then-Mayor Dianne Feinstein’s campaign to rebuild the city’s system in the Eighties. (His anthem “I Left My Heart in San Francisco” also factored into that award.)

At Julien’s Auctions on April 18 and 19, hundreds of those collectibles will be up for grabs, including some of the suits Bennett wore onstage. “He wasn’t Elton John,” Danny Bennett says, “but we have a handful of them.” After Bennett and Stevie Wonder cut a duet of Wonder’s “For Once in My Life,” Wonder bestowed Bennett with the Hohner harmonica he’d played in the studio ($800 to $1,200). A red leather scrapbook, with a preliminary price of $8,000 to $12,000, contains letters to Bennett from Martin Scorsese, Madonna, Robert De Niro, Quincy Jones and Barbra Streisand, among others. Among the priciest items — asking price between $20,000 and $30,000 — is a typed 1965 letter to Bennett from Martin Luther King Jr.; in it, King thanks Bennett for entertaining those in that year’s Selma to Montgomery civil rights march.

What’s clear from the collection — which will be on display at San Francisco’s Fairmont Hotel April 8-10 and then at the Jazz at Lincoln Center building in New York April 10-16 — is that Bennett himself was as much of a souvenir maven as anyone. “He had a collection,” Danny says of his father’s practice of asking for signed souvenirs from his collaborative partners. “It was very personal to him.”

Along with Winehouse, Bennett also had Lady Gaga autograph the sheet music for Rodgers and Hart’s “The Lady Is a Tramp,” which they covered on a duet album. (“Dear Tony, I’ll always be your tramp,” Gaga scribbled. That item is estimated at $1,000 to $1,500.) When Bennett presented the Beatles with an NME award in England 1965, he asked them all to autograph a publicity photo of themselves; that signed shot is going for at least $4,000 to $6,000.

The Bennett family decided to keep many items in the family. Danny himself is holding onto a painting his father created while sitting on the front porch of the Kennedy compound in Hyannis Port, Massachusetts, in the Sixties. “He was close to the Kennedys,” Danny says, “and he wanted me to have that.”

As for the future, Bennett says he’s working on an exhibit of his father’s art and other legacy projects. Later this year, Paramount Plus will finally premiere The Lady and the Legend, a documentary about Bennett’s friendship with Gaga that’s been in the works for several years. First off, though, is the auction and its contents. “It’s better than having it all in a closet somewhere,” Bennett says. “It belongs to the people.”