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Tony Bennett smiling
Tony Bennett's Most Iconic Duets
Frank Sinatra
Tony Bennett was profoundly influenced by Frank Sinatra. As a young man, Bennett idolized Sinatra and said the legendary singer gave him wonderful advice.
Sinatra and Bennett duetted “New York, New York” for Ol’ Blue Eyes’ LP titled “Duets.” In 1965, Sinatra told Life Magazine, “Tony Bennett is the best singer in the business.”
Aretha Franklin
Franklin appeared on "Duets II" performing the tune "How Do You Keep the Music Playing," and in a joint interview, the pair spoke highly of each other.
"It's wonderful just to sing with such a legendary voice," Franklin said of Bennett. Bennett said Franklin was one of “two or three people in the world” that sings “the right way.”
Willie Nelson
For "Duets II," Nelson sat in with Tony Bennett on an absolutely endearing retention of the standard "On the Sunny Side of the Street."
The two legends clearly enjoyed sharing the stage, and it must be noted that Nelson acquitted himself quite well as a crooner, also ripping off a dizzyingly jazzy guitar solo.
Judy Garland
On a 1963 episode of legendary actress and singer Judy Garland's CBS variety show, Bennett and Garland performed an iconic duet of “I Left My Heart in San Francisco.
In his 2012 memoir, Bennett said Garland had given him “One of the best compliments I ever received” by stating he was “the epitome of what entertainers were put on Earth for.”
On the first “Duets” album Sting and Bennett sang a mesmerizing rendition of “Boulevard of Broken Dreams” that beautifully blended their voices.
Bennet’s influence on Sting was evident when he released his own “Duets” album in 2021. Sting said he was “so happy to learn” from Bennett during their collaboration.