Tales of the Jazz Age: Gianni Russo at The Grill Room

Gianni Russo, a k a Connie’s husband.

Gianni Russo, a k a Connie’s husband. (Photo by Steve Barkaszi.)

Walk down Manhattan’s 52nd Street today, and you’ll find few clues that the strip was once a jazz center of New York. Billie Holiday, Miles Davis, Frank Sinatra—all the greats performed here in the ’30s, ’40s and ’50s, in jazz clubs that have since been replaced by Starbucks and glass office buildings.

Wednesday evenings in The Four Seasons Restaurant’s Grill Room, however, Gianni Russo is trying to bring this Golden Age back to life. The flamboyant Mr. Russo—known for playing Carlo Rizzi in The Godfather (“You bastard. You hurt my sister again and I’ll kill you.”)—is also an accomplished singer. For the past two weeks, Mr. Russo has performed a 40-song set for the restaurant’s Wednesday evening crowd, covering classics he once heard Sinatra and others perform live in the 52nd Street clubs.

“We’re going to revive what 52nd Street was,” Mr. Russo told the Transom. “It was the hottest place in New York, long before you were born. Tony Bennett, Nat King Cole—I mean, everybody played this street. When you hear my show, I’ll describe it all.”

Elegantly coiffed patrons—many from the ranks of New York’s business elite—began arriving around 7:30 p.m. to hear Mr. Russo croon. Catalog magnate Lillian Hochberg (of Lillian Vernon) and Sam Waksal, Martha Stewart’s insider trading pal, were spotted separately in the crowd.

But before Mr. Russo had even taken the stage, Four Seasons co-owner Julian Niccolini was already performing. He kissed his longtime patrons—“my regulars,” he called them—before leading them to their tables. He doted on them lavishly, refusing to let them speak of food until they’d at least had a bottle of pink champagne. It didn’t take us long to see that the Grill Room is not so much a restaurant as it is an exclusive club, with Mr. Niccolini serving as its gregarious godfather.

“If Gianni’s no good, we’ll cut his throat,” Mr. Niccolini joked.

As soon as Mr. Russo started singing, accompanied by a four-piece band, it was clear he would survive the night. Some couples danced to his vocal stylings, while others took breaks from their tuna tartare and hamachi ceviche to offer enthusiastic applause. Everyone seemed thrilled by Mr. Russo’s covers of classics like Sinatra’s “The Lady Is a Tramp” and “New York, New York.”

“I think he’s amazing!” gushed Maggie Rady, who told the Transom she’s been dating Mr. Russo for six years. “I’m here every Wednesday!” Ms. Rady was seated at a corner table with some of Mr. Russo’s close friends—an eclectic crew that included a urologist, a restaurateur and a Serbian model.

Radio veteran Bill O’Shaughnessy, who runs Whitney Radio when he (and his magnificent hair) are not circling the New York party scene, was equally thrilled with Mr. Russo’s performance.

“He’s the greatest performer in New York,” Mr. O’Shaughnessy stated. “So many other performers just emote—it’s all about them. Gianni wants to make sure that everybody’s having a good time.”

And it was, indeed, a good time. Mr. Niccolini glided around the room, tipping oysters into patrons’ open mouths and inviting the lucky ones into the kitchen to make the restaurant’s signature cotton candy with one of the pastry chefs. Mr. Russo amicably chatted with guests between songs.

At the end of the night, the Transom was reluctant to step back into the reality of present-day 52nd Street. Luckily, a longtime New Yorker at the table next to us offered an uplifting thought.

“You want to know when the Golden Age is?” he asked. “The Golden Age is now.”