What was the relationship between Tony Bennett and Frank Sinatra?

On Friday, Tony Bennett passed away two weeks shy of his 97th Birthday in his hometown of New York, the news of which was made public by his publicist Sylvia Weiner. No cause of death was stated but the jazz crooner had been diagnosed with Alzheimer’s disease in 2016.

The ‘tenor who sings like a baritone’ garnered fans across generations collaborating with numerous artists from a range of genres. He’s the last of the great saloon singers who came to fame in the 1950s and 1960s like Frank Sinatra, who captivated the native of New York when he was eleven years old.

While Bennett never formed a part of the ‘Rat Pack’, comprised of Sammy Davis Jr., Dean Martin, Joey Bishop, and Peter Lawford and Sinatra, the unofficial leader after Humphrey Bogart died in 1957, he considered Ol’ Blue Eyes his best friend.

What was the relationship between Tony Bennet and Frank Sinatra?

In a salute to Sinatra in Vanity Fair “for showing the way”, Bennett shared his admiration for The Voice which he heard for the first time in 1935. On what was the American Idol of the day, a radio show call Major Bowes’ Amateur Hour, Sinatra captivated the then eleven-year-old Bennett with his confidence.

They would meet for the first time in 1956 when Bennet was asked to fill in for Perry Como on his NBC television show. Bennett was terrified, even though he already had three No. 1 hits, so he sought advice from Sinatra who was at the Paramount Theater. The elder singer told him: “Don’t worry about being nervous. People don’t mind that. It’s when you don’t care that they walk away from you.”

The two built a lasting friendship over the ensuing years and were each other’s fans, often praising the other’s work. In a Life magazine article in 1965 Sinatra spoke candidly about several singers saying “But for my money Tony Bennett is the best singer in the business. [He] gets across what the composer had in mind, and probably a little more.”

Bennett wrote in Vanity Fair: “I like to think that what he heard in my singing was the same honesty that I, and millions of others, found in his.”

Why wasn’t Tony Bennett in the Rat Pack?

You would think that if they were such good friends that Bennett would have been included in what James Wolcott called the “Mount Rushmore of men having fun.” The five members that comprised the group had a reputation of performing and filming movies together in addition to their partying and drinking.

Bennett said that he was never a part of the rabble-rousing club as he couldn’t keep up with them. “I had my singing and my painting, and with the hours they kept — whoa! — it’s just as well I wasn’t in that scene,” he said.