Tony Bennette

This past July, we bade farewell to Tony Bennett, one of the all-time great crooners. Tony Bennett, an artist of whom Frank Sinatra said “is the best singer in the business.”

What made Bennett the best was his unique style. A crooner is a particular type of vocalist, typically a male artist who sings sentimental songs in a soft, smooth, low voice. Think of other great crooners; Andy Williams, Dean Martin, Bing Crosby, and Perry Como. They called Mel Tormé, another celebrated vocalist, The Velvet Fog. But that was not Bennett. Compare his rendition of Don’t Get Around Much Anymore to Tormé’s. Where Tormé smoothly rolls from one phrase to the next, warbling high notes, Bennett cleanly ends each phrase without excessive flourish. Tormé is relaxed, hitting those high notes with seemingly little effort, while Bennett sometimes seems to strain to reach the top of his range. While both are masters, there is an edge to Bennett, something almost foreign to middle-class America in the 1950s.

It was Bennett’s distinctive style that caused his popularity to span generations. Music lovers born long after his first hit in 1951, Rags to Riches, were drawn to Bennett. Artists from Willy Nelson to Amy Winehouse teamed up with him, giving him a reach far beyond the typical crooner audience. Then again, Tony Bennett was far from your typical crooner. Where did Bennett develop this approach to music? What was it about his music that gave him such broad appeal?

Born Anthony Dominick Benedetto on August 3, 1926, at St. John’s Hospital in Queens, New York, to John and Anna Benedetto, Tony was the first of his family to be born in a hospital. Although his father was sickly, ultimately dying when Tony was ten, he instilled a love of the arts in his son. In addition to painting, Tony loved music. Although he listened to such mainstream artists as Judy Garland and Bing Crosby, Tony loved jazz, digging deep into the genre with the likes of Louis Armstrong and Joe Venuti.

He went on to study painting and music at New York’s School of Industrial Art, where he was encouraged by his vocal instructor to explore instrumentalists rather than vocalists, a turn from the well-worn path followed by other singers. At the same time, Tony worked as a singing waiter in Italian restaurants around Queens. One report from this period in his life said that the other waiters and kitchen staff would coach him in singing. It was this combination of scholarly study and practical application that was the foundation for his exclusive brand of music. This continued until he was sixteen, when he dropped out of school to support his family.

Bennett was drafted into the United States Army in 1944, joining the front line in 1945. He would later describe this as a “front-row seat in hell.” He fought his way across Europe, at times involved in house-to-house, town-to-town fighting, narrowly escaping death. Reaching Landsberg, Germany, he was involved in liberating the Kaufering Concentration Camp. He later wrote in his autobiography, “anybody who thinks that war is romantic obviously hasn’t gone through one…I saw things no human being should ever have to see.”

After the war, he returned to the United States, studying music at the American Theatre Wing. There he learned the bel canto singing style. This Italian-originated singing style focused on phrasing, where to emphasize a lyric and staccato, which shortened the duration of a note. You can hear this style when you compare his version of Don’t Get Around Much Anymore with Tormé’s, as suggested above.

In 1949, Pearl Bailey asked him to open for her. This was Bennett’s big break. When Bob Hope saw Bennett perform, he took the singer on the road, which led to a recording contract with Columbia Records. He enjoyed a successful career throughout the 1950s and early 60s. Then came the Beatles and the British Invasion. The dominance of rock put pressure on performers such as Bennett to develop a more contemporary sound. The results were not good. Some of the cuts from Bennett’s rock album, Tony Sings the Great Hits of Today, are embarrassingly bad. Dissatisfied, Bennett left Columbia Records. By the decade’s end, Bennett was not performing and had no recording contract. Tony had hit bottom. In addition to a growing drug addiction, he was living beyond his means and had difficulties with the IRS.

Admitting he was in trouble, Tony reached out to his sons for help. His son Danny took on the role of his father’s manager, booking him on shows ranging from Late Night with David Letterman to The Simpsons. The younger audience liked it. He appeared on the MTV Video Music Awards along with artists such as The Red Hot Chili Peppers and Flavor Flav. The New York Times said, “Tony Bennett had not just bridged the generation gap, he has demolished it.” in 1994, he appeared on MTV Unplugged. The resulting album, MTV Unplugged: Tony Bennett, won the Grammy for Album of the Year as well as winning Tony the Best Traditional Pop Vocal Performance. Although diagnosed with Alzheimer’s in 2016, he continued to work until early 2022. Over his career he sold over 50 million records and won 20 Grammy Awards and two Primetime Emmy Awards.

Returning to the earlier question, what was it about his music that gave him such broad appeal? Philip Toshio Sudo wrote in his book Zen Guitar, “It’s not enough to simply find the means to express this sound [music]…You must find your sound and dig into it until you reach its very source…Whatever obstacles you face, never stop listening to the sound inside you.” This is what makes Tony Bennett’s music great. In all those years of listening, studying, and applying what he learned, he found his sound. He remained loyal to that sound even when it meant ending his contract with Columbia Records. It was a sound that was true. For that reason, that sound resonated with so many of us, even those of a younger generation.

For more on Italian and Italian-American culture, read my book Italianità, The Essence of Being Italian .