In the early 2000s, one of Frank Sinatra’s old stomping grounds was reborn when Jilly’s reopened on 41 West 58th Street. For many years, Sinatra and his Rat Pack gang frequented the old place on 256 West 52nd Street, which is now home to the Russian Samovar. They used to hang out there until the wee small hours of the morning. The popular celebrity hang had been owned by Jilly Rizzo, a colorful character and longtime Sinatra pal, who ran his joint from the 50s to 70s before he headed out west. So when I learned that Jilly’s would be given a new life and twist, I was extremely excited as I was much too young to experience the original saloon.

I was working in Tribeca at the time as the General Manager of the upscale Italian restaurant Scalini Fedeli, run by chef Michael Cetrulo. After finishing my night at Scalini, I would typically take a cab to Jilly’s for a few nightcaps, from which point I could walk—or frequently stagger—back to my house a few blocks away. It was a perfect place for me to end my night—a small, cozy room with a piano—just my kind of place. So once I wet my feet there, it was time to tell my gang of misfits that this would be our new hang.

The manager of the establishment was a man by the name of Anthony Mazzola, who worked with a smart, raven-haired beauty with a great sense of style, named Carey Smith. Together, they were incredibly courteous and frequently went above and beyond to make you feel at home, making them the ideal hosts for the type of folks who frequented the establishment. On one occasion, I was fortunate to attend Nancy Sinatra’s after-party, as she was in town performing at Irving Plaza. Some of her band members were part of the famed Wrecking Crew and her guitarist, Gilby Clarke, was formerly of Guns & Roses. It was a special night and many of her New York friends turned out to see her, including Little Steven Van Zandt, who was then my neighbor. At one point, I spotted bassist Christian McBride smoking a cigar at the bar and grabbed him to introduce him to Nancy and her daughter AJ. He was thrilled as he had never met a Sinatra. (Today, he’s still in touch with them from that initial introduction, and I reunited with AJ not too long ago when she returned to New York to perform at 54 Below.)

On another occasion, Robert Plant was staying at The Plaza hotel just down the street for a week while opening for The Who at Madison Square Garden. After his performance, he would go over to Jilly’s for a few drinks and to unwind. He had been dropping by intermittently all week. On one of those evenings, one manager called me to say that Plant had just walked in again with a gorgeous blonde, and since I lived only a few blocks away, I should come over. That wasn’t even a decision I had to make. I bolted over, as I was such a huge Led Zeppelin fan.

That week, Louis Vanaria—who at 17 had made his acting debut in the film A Bronx Tale—was singing at the club with pianist John Colianni supporting him. It seemed like Plant had been enjoying the music and kept returning for more. But on this night, Vanaria had prepared an uptempo swing-style version of A Stairway to Heaven, expecting that Plant would return. Sure enough, he did. When I got to the club, they were playing it while Plant and his companion were listening intently from the bar while sipping their Chardonnay. As Louis was swinging the song, he would tease Plant about the lyrics, which amused him. Vanaria would rib Plant, and say something after he’d sung the lyrics,

There’s a feeling I get when I look to the west

And my spirit is crying for leaving.

Hey Robert, ”What the fuck does that mean?” This went on for a while and at each point during the song, as Vanaria was mocking Plant, I’d see Plant get closer to the stage until he was right in front of Vanaria. At that point, Plant grabbed the mic and started singing his own song. The place then went nuts. We were being given a private show from none other than Zeppelin’s frontman. It was electric. After he ended his most famous song, he whispered to the pianist and said that he hadn’t sung or played that song since 1979, because he got sick of hearing inferior versions of it. But this version inspired him, he intimated. From there he began singing the Nat King Cole hit, Nature Boy. I just couldn’t believe what was happening.

After Plant sang a few more songs, we all went to the bar and got smashed with him. It was a night to remember, and it was all courtesy of Frank and Jilly. Thanks, guys!

RECOMMMEDED

Charles Carlini

Former restauranteur, musician, concert promoter, producer, publisher, manager, and impresario, Charles Carlini has synthesized these roles to become a dynamic force in the music industry–noted for his ability to bring diverse talent together to create innovative concerts and recordings that reach and move music-lovers everywhere.