Inside the Long, Complicated and Colorful Life of Iconic Singer Tony Bennett

The Italian-American singer is an exponent of traditional pop, big band, show melodies, and jazz. He has created works as a painter, which are exhibited publicly in several institutions. And if that's not enough, he is also the founder of the Frank Sinatra School of Arts.

Anthony Dominick Benedetto, born August 3, 1926, Astoria, Queens, New York, U.S., the son of a grocer, spent his boyhood in Astoria, New York, studying singing and painting. He served three years in the army during World War II and embarked on a singing career in 1949.

Bennett’s break came the following year when Bob Hope heard him in a nightclub and invited him to share the stage during Hope’s engagement. Bennett was working under the stage name of Joe Bari, which Hope thought was hard to remember so he rechristened the young singer Tony Bennett.

Tony Bennett I Image: Getty Images

Tony Bennett I Image: Getty Images


Young Tony grew up listening to Al Jolson, Eddie Cantor, Judy Garland, and Bing Crosby as well as jazz artists such as Louis Armstrong, Jack Teagarden, and Joe Venuti. By age 10 he was already singing, and performed at the opening of the Triborough Bridge, standing next to Mayor Fiorello La Guardia.

The song “Boulevard of Broken Dreams” became Bennett’s first hit recording in 1951 and was followed by several records that topped the charts during the next few years: “Because of You,” “Cold, Cold Heart,” “Stranger in Paradise,” “Just in Time,” and “Rags to Riches.”

Tony Bennett I Image: Getty Images

Tony Bennett I Image: Getty Images


Bennett married art student and jazz fan Patricia Beech, on February 12, 1952, whom he had met the previous year after a nightclub performance in Cleveland. The couple had two sons, D’Andrea, Danny, born 1954 and Daegal, Dae, born in 1955).

He returned to the top of the singles charts in 1962 with his biggest hit, “I Left My Heart in San Francisco,” the song with which he remains most associated. Other hit recordings during the 1960s included “I Wanna Be Around,” “The Good Life,” and “Who Can I Turn To.”


“Stranger in Paradise” was also a number-one hit in the United Kingdom a year and a half later and started Bennett’s career as an international artist. For a month in August-September 1956, Bennett hosted a Saturday night television variety show, The Tony Bennett Show.

Tony Bennett I Image: Getty Images

Tony Bennett I Image: Getty Images

Bennett’s albums, nearly all of the Grammy Award winners or nominees, sold in the millions. Several albums Bennett made in tribute to other artists, such as Frank Sinatra (Perfectly Frank, 1992), Fred Astaire (Steppin’ Out, 1993), and Duke Ellington (Hot & Cool: Bennett Sings Ellington, 1999).

Bennett’s son and personal manager, Danny Bennett, began an aggressive campaign to market his father to a wider audience, and the following years proved to be the most successful and critically praised period of Bennett’s career.

Bennett continued to record and tour steadily, doing a hundred shows a year by the end of the century. In concert Bennett often makes a point of singing one song (usually “Fly Me to the Moon”) without any microphone or amplification, demonstrating his skills at vocal projection.


He had no intention of retiring, saying in reference to masters such as Pablo Picasso and Fred Astaire: “right up to the day they died, they were performing. If you are creative, you get busier as you get older.”

In the late 1980s, Bennett entered into a romantic relationship with Susan Crow, a former New York City schoolteacher who was 33 years his junior. On June 21, 2007, Bennett married Crow in a private civil ceremony in New York.

Bennett and Crow founded “Exploring the Arts,” a charitable organization dedicated to creating, promoting, and supporting arts education. At the same time, they founded “the Frank Sinatra School of the Arts in Queens,” a public high school dedicated to teaching the performing arts.


Bennett has also had success as a painter, done under his real name of Anthony Benedetto or just Benedetto. He followed up his childhood interest in professional training, work, and museum visits throughout his life.

He sketches or paints every day, often of views out of hotel windows when he is on tour. He has exhibited his work in numerous galleries around the world. He was chosen as the official artist for the 2001 Kentucky Derby and was commissioned by the United Nations to do two paintings.


Bennett has released over 70 albums during his career. The singer has won 18 Grammy Awards including a Grammy Lifetime Achievement Award.

He celebrated his 80th birthday with “Duets: An American Classic.” Bennett was joined by a wide range of collaborators on the project, from country “the Dixie Chicks” to Colombian pop star Juanes to contemporary crooner Michael Bublé.

At age 85, Bennett was the oldest living artist to top the Billboard charts. “Body and Soul” won a Grammy for best pop performance by a duo or group, and Duets II was awarded Best Traditional Pop Vocal Album.

Tony Bennett I Image: Getty Images

Tony Bennett I Image: Getty Images

Cheek to Cheek (2014) was an album of jazz recorded with pop artist Lady Gaga. She gave Bennett a giant birthday cake onstage at a recent concert in celebration of his 89th birthday.

Bennett’s basic style changed little throughout the years, although many persons feel that his voice and interpretive skills improved with the time. With a recognizable voice, he mastered all genres, from intimate ballads and up-tempo swing numbers to contemporary pop.

Today Tony Bennett's artistry and accomplishments are applauded here at home and all over the world from people from 12- to 90-years old.

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