“People forget how crazy the city was,” he said. “But also, it was still an era where most people that you’d meet — what’s the line? The people who didn’t fit in anywhere else would move here.”

To engage with Mr. Willner at 61 is to enter a world where freak shows and Soupy Sales are still a salient presence. For nearly four decades, he has worked to consolidate the margins of American culture into his own idiosyncratic mainstream.

His first big idea, at age 24, was to gather a bunch of jazz musicians to reimagine the music from Federico Fellini’s films. It was a screwy idea. It was 1980, and no one was buying jazz records or soundtracks by Nino Rota, Fellini’s composer. Mr. Willner was driving a cab at the time, starting his shift at 5 a.m. at the Paradise Garage or other clubs. The idea did not seem screwy to him. It was the music he heard in his head.

He found money somewhere, and willing participants: Debbie Harry and Chris Stein from Blondie; a very young Wynton Marsalis and youngish Henry Threadgill, among others. Then he went to Rome to ask Fellini for the rights.

“I was speechless when I went to Fellini’s door,” Mr. Willner said. “It was like meeting Dickens. I noticed that he had all these Laurel and Hardy books. So I mentioned it, and he said, ‘Yes, what else is there?’ We were doing Laurel and Hardy with each other.

“He said, ‘We go to lunch now.’ And he takes these two actresses who were in ‘City of Women,’ voluptuous, and he orchestrated the whole lunch, and then drove me around Rome. And dropped me off in the middle of somewhere: ‘I leave you to your destiny.’”

That first album, “Amarcord Nino Rota,” gave Mr. Willner a taste of what was possible, especially if he did not draw borders between types of music or musicians — between jazz and rock, between punk and mainstream. He could get Todd Rundgren and Dr. John to play the music of Thelonious Monk; he could get Sinead O’Connor or the Replacements to play songs from Disney cartoons. If he combined the right musicians in unfamiliar pairings, the results might be something not heard before, even in the minds of the players.