After having achieved artistic and commercial success in the 1950s and early 1960s, his career suffered an extended downturn during the height of the rock music era. However, Bennett staged a remarkable comeback in the late 1980s and 1990s, expanding his audience to a younger generation while keeping his musical style intact. He remains a popular and critically praised recording artist and concert performer in the 2000s.
Tony Bennett is also a serious and accomplished painter.
Anthony Dominick Benedetto was born in the Astoria section of Queens in New York City. (Though some records show that the first name on his birth certificate is Antonio.) His father was a grocer and his mother a seamstress.
He grew up listening to Al Jolson, Eddie Cantor, Judy Garland, Bing Crosby, and jazz artists such as Louis Armstrong, Jack Teagarden, and Joe Venuti. An uncle was a tap dancer in vaudeville, giving him an early window into show business.
By age 10 the young Benedetto was already singing, performing at the opening of the Triborough Bridge. He attended New York's High School of Industrial Arts where he studied music and painting (an interest he would always return to as an adult), but dropped out at age 16 to help support his family. He then set his sights on a professional singing career, performing as a singing waiter in several Queens Italian restaurants.
World War II and afterThis was interrupted when Benedetto was drafted into the United States Army in 1944 during World War II. He served as a replacement infantryman in the U.S. 63rd Infantry Division in France and Germany, moving across France during the winter, then fighting on the front lines in March and April 1945 as the Germans were pushed back across the Rhine. Benedetto narrowly escaping death several times. He would later write, "Anybody who thinks that war is romantic obviously hasn't gone through one." At the war's conclusion he was involved in the liberation of a Nazi concentration camp near Landsberg.
Benedetto stayed in Germany as part of the occupying force, but was assigned to an informal Special Services band unit that would entertain nearby American forces. Later some remarks he made against the Army's racial segregation policies led to his being demoted and reassigned to Graves Registration duties, leading to a further dislike of the military.  Subsequently he sang with the Army military band under the stage name Joe Bari and played with many musicians who would have post-war careers.
Upon his discharge from the Army and return to the States in 1946 he studied at the American Theater Wing on the GI Bill. He was taught the bel canto singing discipline, which would keep his voice in good shape for his entire career. He continued to perform wherever he could, including while waiting tables. He developed an unusual style of phrasing that involved imitating other musicians – such as Stan Getz's saxophone or Art Tatum's piano – as he sang, thus allowing him to improvise as he interpreted a song.
In 1949 Pearl Bailey spotted his talent and asked him to open for her in Greenwich Village. She had invited Bob Hope to the show; Hope decided to bring Bari on the road with him, but suggested he use his real name simplified to Tony Bennett. In 1950 Bennett cut a demo and was signed to Columbia Records by Mitch Miller.
Warned by Miller not to imitate Frank Sinatra (who was just then leaving Columbia), Bennett began his career as a crooner singing commercial pop tunes. His first big hit was "Because of You", a ballad produced by Miller with a lush orchestral arrangement from Percy Faith. It started out gaining popularity on jukeboxes, then reached #1 on the pop charts in 1951 and stayed there for 10 weeks, selling over a million copies. This was followed to the top later that year by a similarly-styled rendition of Hank Williams' "Cold, Cold Heart", which helped introduce Williams and country music in general to a wider, more national audience. The Miller and Faith tandem continued to work on all of Bennett's early hits. Bennett's recording of "Blue Velvet" was also very popular and attracted screaming teenage fans at concerts in the famed Paramount Theatre in New York (Bennett did 7 shows a day, starting at 10:30 a.m.) and elsewhere.
In 1952 Bennett married Ohio art student and jazz fan Patricia Beech, whom he had met the previous year after a nightclub performance in Cleveland. Two thousand female fans dressed in black gathered outside the ceremony at New York's St. Patrick's Cathedral in mock mourning. Bennett and Beech would have two sons, D'Andrea (Danny) and Daegal (Dae).
A third #1 came in 1953 with "Rags to Riches". Unlike Bennett's other early hits, this was an up-tempo big band number with a bold, brassy sound and a double tango in the instrumental break; it topped the charts for eight weeks. Later that year Bennett began singing show tunes to make up for a New York newspaper strike; "Stranger in Paradise" from the Broadway show Kismet reached the top, as well as being a #1 hit in the United Kingdom and starting Bennett's career as an international artist.
Once the rock and roll era began in 1955, the dynamic of the music industry changed and it became harder for existing pop singers to do as well commercially. Nevertheless Bennett continued to enjoy success, placing 8 songs in the Billboard Top 40 during the latter part of the 1950s, with "In the Middle of an Island" reaching the highest at #9 in 1957.
In 1956 Bennett hosted the television variety show The Tony Bennett Show as a summer replacement for The Perry Como Show.
A growing artistryIn 1955 Bennett released his first long-playing album, Cloud 7, which showed Bennett's jazz leanings. In 1957 Ralph Sharon became Bennett's pianist and musical director. Sharon told Bennett that a career singing "sweet saccharine songs like 'Blue Velvet'" wouldn't last long, and encouraged Bennett to focus even more on his jazz inclinations.
The result was the 1957 album Beat of My Heart. It used well-known jazz musicians such as Herbie Mann and Nat Adderley, with a strong emphasis on percussion from the likes of Art Blakey, Jo Jones, Latin star Candido, and Chico Hamilton. The album was both popular and critically praised.
Bennett followed this by working with the Count Basie Orchestra, becoming the first male pop vocalist to sing with Basie's band. The albums Basie Swings, Bennett Sings (1958) and In Person! Tony Bennett/Count Basie and his Orchestra (1959) were the well-regarded fruits of this collaboration, with "Chicago" being one of the standout songs.
Bennett also built up the quality and reputation of his nightclub act; in this he was following the path of Sinatra and other top jazz and standards singers of this era. Bennett also appeared on television; he sang on the first night of both the Johnny Carson The Tonight Show and The Merv Griffin Show. In June 1962 Bennett staged a highly-promoted concert performance at Carnegie Hall, using a stellar lineup of musicians including Al Cohn, Kenny Burrell, and Candido, as well as the Ralph Sharon Trio. The concert featured 44 songs, including favorites like "I've Got the World on a String" and "The Best Is Yet To Come". It was a big success, and further cemented Bennett's reputation as a star both at home and abroad.
Also in 1962 Bennett released the song "I Left My Heart in San Francisco". Although this only reached #19 on the Billboard Hot 100, it spent close to a year on various other charts and increased Bennett's exposure. The album of the same title was a top 5 hit and both the single and album achieved gold record status. The song won Grammy Awards for Record of the Year and Best Male Solo Vocal Performance, and over the years would become known as Bennett's signature song. In 2001 it was ranked 23rd on an RIAA/NEA list of the most historically significant Songs of the 20th Century.
Bennett's following album, I Wanna Be Around (1963) was also a top 5 success, with the title track and "The Good Life" each reaching the top 20 of the pop singles chart and the top 10 of the Adult Contemporary chart.
The next year brought The Beatles and the British Invasion, and with them still more musical and cultural attention to rock and less to pop, standards, and jazz. Over the next couple of years Bennett had minor hits with several albums and singles based on show tunes – his last top 40 single was the #34 "If I Ruled the World" from Pickwick in 1965 – but his commercial fortunes were clearly starting to decline. An attempt to break into acting with a role in the 1966 film The Oscar was not well received.
A firm believer in the American Civil Rights movement, Bennett participated in the 1965 Selma to Montgomery marches. Years later he would continue this commitment by refusing to perform in apartheid South Africa.
Years of struggle
Sharon and Bennett parted ways in 1965. There was great pressure on singers such as Lena Horne and Barbra Streisand to record "contemporary" rock songs, and in this vein Columbia Records' Clive Davis suggested that Bennett do the same. Bennett was very reluctant, and when he tried, the results pleased no one. This was exemplified by Tony Sings the Great Hits of Today! (1969), which featured misguided attempts at Beatles and other current songs and a ludicrous psychedelic cover.
Years later Bennett would recall his dismay at being asked to do contemporary material, comparing it to when his mother was forced to produce a cheap dress. By 1972 he had departed Columbia for MGM Records, but found no more success there, and in a couple more years he was without a recording contract.
Bennett and his wife Patricia had been separated since 1965, their marriage a victim of too much time on the road among other factors, and in 1971 their divorce became official. Bennett had been involved with aspiring actress Sandra Grant since filming The Oscar, and in 1972 they married. They would have two daughters, Joanna and Antonia.
Hoping to take matters into his own hand, Bennett started his own record company, Improv. He cut some songs that would later become favorites, such as "What is This Thing Called Love?", and made two well-regarded albums with jazz pianist Bill Evans, The Tony Bennett/Bill Evans Album (1975) and Together Again (1976), but by 1977 Improv was out of business. A stint of living in England like other American jazz expatriates did not change his fortunes.
As the decade neared its end, Bennett had no recording contract, no manager, and was not performing any concerts outside of Las Vegas. His second marriage was failing (they would divorce in 1980). He had (like many musicians) developed a drug addiction, was living beyond his means, and had the Internal Revenue Service trying to seize his Los Angeles home. He had hit bottom.
After a near-death cocaine overdose in 1979, Bennett called his sons Danny and Dae for help. "Look, I'm lost here," he told them. "It seems like people don't want to hear the music I make."
Danny Bennett, an aspiring musician himself, also came to a realization. The band Danny and his brother had started, Quacky Duck and His Barnyard Friends, had foundered and Danny's musical abilities were limited. However he had discovered during this time, that he did have a head for business. His father, on the other hand, had tremenedous musical talent but was having trouble sustaining a career from it. Danny signed on as his father's manager.
Danny got his father's expenses under control, moved him back to New York, and began booking him in colleges and small theatres to get him away from a "Vegas" image. Also in 1979, Tony Bennett reunited with Ralph Sharon as his pianist and musical director.
By 1986, Tony Bennett was re-signed to Columbia Records, this time with creative control, and released The Art of Excellence. This became his first album to reach the charts since 1972.
An unexpected audience
By the mid-1980s, the excesses of the disco, punk rock, and new wave eras had given many artists and listeners a greater appreciation for the classic American song. Rock stars such as Linda Ronstadt began recording albums of standards, and such songs began showing up more frequently in movie soundtracks and on television commercials.
Danny Bennett felt strongly that younger audiences, although completely unfamiliar with Tony Bennett, would respond to his music if only given a chance to see and hear it. More crucially, no changes to Tony's appearance (tuxedo), singing style (his own), musical accompaniment (The Ralph Sharon Trio or an orchestra), or song choice (generally the Great American Songbook) were necessary or desirable.
Accordingly, Danny began to book his father on shows with younger audiences, such as David Letterman's talk shows, The Simpsons, and various MTV programs. The plan worked; as Tony later remembered, "I realized that young people had never heard those songs. Cole Porter, Gershwin – they were like, 'Who wrote that?' To them, it was different. If you're different, you stand out."
During this time, Bennett continued to record, first putting out the acclaimed look back Astoria: Portrait of the Artist (1990), then emphasizing themed albums such as the Sinatra homage Perfectly Frank (1992) and the Fred Astaire tribute Steppin' Out (1993). The latter two both achieved gold status and won Grammies for Best Traditional Pop Vocal Performance (Bennett's first Grammies since 1962) and further established Bennett as the inheritor of the mantle of a classic American great.
As Bennett was seen at MTV Video Music Awards shows side by side with the likes of the Red Hot Chili Peppers and Flavor Flav, and as his "Steppin' Out With My Baby" video received MTV airplay, it was clear that, as The New York Times said, "Tony Bennett has not just bridged the generation gap, he has demolished it. He has solidly connected with a younger crowd weaned on rock. And there have been no compromises."
The new audience reached its height with Bennett's appearance in 1994 on MTV Unplugged. Featuring guest appearances by rock and country stars Elvis Costello and k.d. lang (both of whom had a profound respect for the standards genre), the show attracted a considerable audience and much media attention. The resulting album went platinum and, besides taking the Best Traditional Pop Vocal Performance Grammy award for the third straight year, also won the top Grammy prize of Album of the Year. At age 68, Tony Bennett had come all the way back.
No retirementSince then Bennett has continued to record and tour steadily. In concert Bennett often makes a point of singing one song (usually "Fly Me to the Moon") without any microphone or amplification, demonstrating to younger audience members the lost art of vocal projection. One show, Tony Bennett's Wonderful World: Live From San Francisco, was made into a PBS special. Bennett also created the idea behind, and starred in the first, of the A&E Network's Live By Request series, for which he won an Emmy Award.
A series of albums, often based on themes (Duke Ellington, Louis Armstrong, Billie Holiday, blues, duets) have met with good acceptance; Bennett has won five more Best Traditional Pop Vocal Performance or Best Traditional Pop Vocal Album Grammies in the subsequent years, most recently in 2003. According to his official biography, Bennett has now sold over 50 million records worldwide during his career.
In addition to numerous television guest performances, Bennett has had cameo appearances as himself in films such as The Scout, Analyze This, and Bruce Almighty.
Tony Bennett's career as a painter has also flourished. He followed up his childhood interest with serious training, work, and museum visits throughout his life. He sketches or paints every day, even of views out of hotel windows when he is on tour. Painting under his real name of Benedetto, he has exhibited his work in numerous galleries and has been commissioned by the Kentucky Derby and the United Nations. His painting "Homage to Hockney" (for his friend David Hockney) is on permanent display at the highly regarded Butler Institute of American Art in Youngstown, Ohio as is his "Boy on Sailboat, Sydney Bay" at the National Arts Club in Gramercy Park in New York. His paintings have been featured in ARTNews and other magazines. Many of his works were published in the art book Tony Bennett: What My Heart Has Seen in 1996.
Bennett also published The Good Life: The Autobiography of Tony Bennett in 1998.
For his contribution to the recording industry, Tony Bennett has a star on the Hollywood Walk of Fame at 1560 Vine Street.
Bennett was inducted into the Big Band and Jazz Hall of Fame in 1997.
Bennett received a lifetime achievement award from the American Society of Composers, Authors, and Publishers (ASCAP) in 2002.
In 2002 Q magazine named Tony Bennett in their list of the "50 Bands To See Before You Die".
Bennett frequently donates his time to charitable causes, to the extent that he is sometimes nicknamed "Tony Benefit".
Bennett has not remarried, but has a long-term relationship with Susan Crow, a former New York City educator. Together they founded (and named after Bennett's friend) the Frank Sinatra School of the Arts in Queens, a public high school dedicated to teaching the performing arts which opened in 2001. It was a tribute in return, for in a 1965 Life magazine interview Sinatra had said that:
"For my money, Tony Bennett is the best singer in the business. He excites me when I watch him. He moves me. He's the singer who gets across what the composer has in mind, and probably a little more."
Danny Bennett continues to be Tony's manager while Dae Bennett is a recording engineer who has worked on a number of Tony's projects and who has opened Bennett Studios in Englewood, New Jersey. Tony's younger daughter Antonia is an aspiring jazz singer.
Bennett will be a recipient of a Kennedy Center Honor in 2005.