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Nearly 22 years after the premiere of The Sopranos, the classic mob/family show only seems to be gaining fans. It’s not a mystery why that’s happening. Whether you scrutinize the storylines, the acting, the directing, or the cinematography, most of it holds up two decades later.

You can say the same about the use of music on The Sopranos. As TV shows go, only Miami Vice is in the same league, and The Sopranos did it without incidental (i.e., background) music. Nearly everything you hear had to be licensed for use on TV. And it often got expensive (see: that Led Zeppelin track).

Once The Sopranos became a hit, recording artists began to lobby the show’s producers to get their songs on the soundtrack. (Even Bob Dylan wanted in on the action.) However, when The Sopranos contacted Prince about using his music, the legendary songwriter-performer replied that it would be a no-go.

Prince denied the request by ‘The Sopranos’ producers to use 1 of his songs on the show

Prince on stage in 1992
Prince performs at Earl’s Court, London, June 1992. | Dave Benett/Getty Images

If you want to know about the use of music on The Sopranos, producer Martin Bruestle is the one to seek out. Over the series’ 86-episode run, Bruestle handled post-production duties alongside creator David Chase. And a significant part of Bruestle’s job was the music.

On the Talking Sopranos podcast, Bruestle spoke about clearing the rights to the publishing (i.e., the sheet music) as well as the master recordings of various songs. Bruestle enjoyed great success nabbing the industry’s biggest names (including the previously impossible-to-get Zeppelin).

“Ric Ocasek from The Cars called me and loved the music,” Bruestle said. “And [Chic founder] Nile Rodgers, the producer, loved the music. Jerry Vale wanted me to have his music on the show.” And Bruestle recalled artists sending him music for his consideration.

Bruestle didn’t receive any such request from Prince, however. And when The Sopranos producers reached out to The Purple One to use a song of his (circa 2002), Prince’s people replied that they wouldn’t be licensing anything for the show.

Prince also dissed ‘Sopranos’ star Michael Imperioli in an unrelated ’90s incident

'Sopranos' still
Tony Sirico, Steven Van Zandt and James Gandolfini in a publicity still for ‘The Sopranos’ | Anthony Neste/The LIFE Images Collection via Getty Images
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Prince’s rejection of that song request wasn’t the first time he dissed something Sopranos-related. Michael Imperioli, who played Christopher Moltisanti, felt the sting of Prince’s rejection years before The Sopranos began to air on HBO.

On the occasion in question, Imperioli was attending a party after the completion of Spike Lee’s Girl 6 (1996). Imperioli acted in the film, and Prince had handled the soundtrack for Lee. When Imperioli tried to greet Prince in the VIP section at the party, The Artist’s handlers told Imperioli to go away.

“His two bodyguards — a man and a woman — stepped in front of me,” Imperioli recalled previously on Talking Sopranos. “And one of them says, ‘Can you not look at him, please?’ I was stunned.” Indeed, it turns out Prince never wanted anything to do with The Sopranos. And he apparently knew that before the show existed.