Tony Bennett left his heart in Chicago, too

Tony Bennett was Mr. New York.

Born and raised in the Astoria neighborhood in the borough of Queens, Anthony Benedetto lived and breathed the Big Apple. He later made his home in Manhattan, where he took walks in Central Park and painted by the sunlight cascading through windows overlooking the urban oasis. He rehearsed songs at the side of a grand piano in his, ahem, tony apartment, songs he knew like the back of his hand, but never performed the same way twice.

He immortalized San Francisco with his signature song. That city’s Fairmont Hotel — where he performed many, many times over the course of a 70-year-career at its Venetian Room, and where in 1961 he first publicly performed “I Left My Heart in San Francisco” — features a life-sized bronze statue in tribute to him. (The song earned him his first two of 19 Grammy Awards over the course of his career.)

But mention Chicago during the course of a conversation (or two or three) with Bennett, and his seemingly omnipresent smile would grow even larger. His love for the Windy City ran deep.

Miriam Di Nunzio

Of course there was Mayor Richard M. Daley’s proclamation of “Tony Bennett Day” in Chicago in 1993.

But long before that, there were the 1960s and 1970s at Chicago jazz hubs such as Mister Kelly’s or London House, where many times Bennett would take in a set from some of the best in the business (hello, Erroll Garner), or perform a scheduled gig of his own. Then there were the headlining shows at Hugh Hefner’s Playboy clubs in the Gold Coast and Lake Geneva.

There was Highland Park’s Ravinia, where Bennett performed more than 40 times over the course of nearly as many years in the sweltering August heat to adoring throngs (his concerts were among the biggest sellers in the history of the outdoor venue). He often referred to Ravinia as one of his “favorite summer homes.”

And what was a visit to Chicago without a stop at his beloved Rosebud restaurant?

JON SALL/SUN-TIMES, FILE

“Absolutely, he was Mr. Ravinia,” said Welz Kauffman, the former president and CEO of Ravinia. (Bennett’s sincere fondness for the sprawling outdoor concert site can be seen in his oil painting of the festival grounds, “Ravinia: Music Under the Stars,” presented to the venue in 1988.)

“His many, many performances there thrilled and delighted audiences with his shear sense of joy,” Kauffman said “You’d hear the same set list sometimes, but it didn’t matter because no one could touch his artistry. ... And he was always thinking about Ravinia and its continued success and how to move it into the next century. ... That’s why he brought Lady Gaga with him to Ravinia, because he felt [the duo] was not about the past and the present, but about the present and the future.”

Lunch or dinner in Chicago for Bennett was almost always at Rosebud on Taylor Street, and later at the River North location, where Alex Dana, owner/founder of Rosebud Restaurants Group, welcomed his friend of more than 40 years with open arms, a window-side table and plenty of “al dente pasta with red sauce.”

“He really just loved simple food,” Dana said. “You could talk up everything on the menu, but he’d say gimme me the pasta and red sauce. Al dente. He always wanted the bucatini, or the linguini.”

And Bennett would eagerly oblige fellow diners’ requests, autographing their cocktail napkins.

Courtesy Rosebud Restaurants

The two would also share visits to jazz clubs around town, especially the famed Gold Star Sardine Bar, to “take in a set by (jazz singer/guitarist) Frank D’Rone.”

Or they’d head over to the Art Institute for the afternoon, where Bennett, an acclaimed painter and longtime supporter of arts education in schools, would enlighten his restaurateur pal on his favorite paintings.

And when it seemed like Bennett’s career was on its way out in the 1970s, and Dana’s restaurant wasn’t quite yet successful, it was the singer who encouraged his Chicago pal not to lose faith.

“I don’t know if Bennett was a religious person, but I’ll never forget he told me, ‘You’re gonna build a business, and I’m gonna build a career.’ And we did,” Dana said.

Sun-Time File

There was also Bennett’s work on behalf of the Civil Rights Movement, that saw him walking alongside the Rev. Martin Luther King Jr. during the march from Selma to Montgomery in 1965.

On Twitter Friday, the Rev. Jesse Jackson paid tribute to his good friend, noting Bennett’s lifelong commitment to civil rights.

“He was dedicated to civil and human rights and to the arts. He will live as long as we remember him,” Jackson tweeted.

In a 2006 interview, I asked Bennett about his signature song, and if he loved performing it as much as fans loved hearing it.

“‘I Left My Heart in San Francisco’ will be my greatest legacy,” Bennett said, “There’s so much fear out there these days, in the world we live in. ... So if that song, if what I do with musicians and other singers, can help people forget their troubles, forget their pain, forget their fears for a little while, I can’t ask for any greater legacy.”