Anthony Benedetto was born in Astoria, Queens, New York City, the son of Ann (née Suraci) and John Benedetto. His father was a grocer who had emigrated from Podàrgoni, a rural eastern district of the southern Italian city of Reggio Calabria, and his mother was a seamstress. With two other children and a father who was ailing and unable to work, the siblings grew up in poverty. John Benedetto died when Anthony was 10 years old.

Young "Tony" Benedetto 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. An uncle was a tap dancer in vaudeville, giving him an early window into show business.By age 10 he was already singing, and performed at the opening of the Triborough Bridge. Drawing and caricatures were also an early passion of his.He attended New York's High School of Industrial Art where he was studying painting and music, but dropped out at age 16 to help support his family. He worked as a copy boy and runner for the Associated Press in Manhattan. But mostly he set his sights on a professional singing career, performing as a singing waiter in several Italian restaurants around the borough of Queens.

Benedetto was drafted into the United States Army in November 1944, during the final stages of World War II. He did basic training at Fort Dix and Fort Robinson as part of becoming an infantry rifleman. Benedetto ran afoul of a sergeant from the South who disliked the Italian from New York City and heavy doses of KP duty or BAR cleaning resulted. Processed through the huge Le Havre replacement depot, in January 1945, he was assigned as a replacement infantryman to 255th Infantry Regiment of the 63rd Infantry Division, a unit filling in for the heavy losses suffered in the Battle of the Bulge. He moved across France, and later, into Germany. As March 1945 began, he joined the front line and what he would later describe as a "front-row seat in hell."

As the German Army was pushed back to their homeland, Benedetto and his company saw bitter fighting in cold winter conditions, often hunkering down in foxholes as German 88 mm guns fired on them. At the end of March, they crossed the Rhine and entered Germany, engaging in dangerous house-to-house, town-after-town fighting to clean out German soldiers; during the first week of April, they crossed the Kocher River, and by the end of the month reached the Danube. During his time in combat, Benedetto narrowly escaped death several times. The experience made him a patriot and also a pacifist; 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, where some American prisoners of war from the 63rd Division had also been held.

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. His dining with a black friend from high school — at a time when the Army was still segregated — led to his being demoted and reassigned to Graves Registration Service duties. Subsequently, he sang with the 314th Army Special Services Band under the stage name Joe Bari (a name he had started using before the war, chosen after the city and province in Italy and as a partial anagram of his family origins in Calabria). He played with many musicians who would have post-war careers.

Upon his discharge from the Army and return to the States in 1946, Benedetto studied at the American Theatre 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 approach that involved imitating, as he sang, the style and phrasing of other musicians—such as that of Stan Getz's saxophone and Art Tatum's piano—helping him to improvise as he interpreted a song. He made a few recordings as Bari in 1949 for small Leslie Records, but they failed to sell.

In 1949, Pearl Bailey recognized Benedetto's talent and asked him to open for her in Greenwich Village. She had invited Bob Hope to the show. Hope decided to take Benedetto on the road with him, but suggested he use his real name simplified as Tony Bennett. In 1950, Bennett cut a demo of "Boulevard of Broken Dreams" and was signed to the major Columbia Records label 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 of the charts 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 teenaged fans at concerts at the famed Paramount Theater in New York (Bennett did seven shows a day, starting at 10:30 a.m.) and elsewhere.

On February 12, 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, born around 1954) and Daegal (Dae, born around 1955).

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 the producers of the upcoming Broadway musical Kismet had Bennett record "Stranger in Paradise" as a way of promoting the show during a New York newspaper strike. The song reached the top, the show was a hit, and Bennett began a long practice of recording show tunes. "Stranger in Paradise" was also a #1 hit in the United Kingdom a year and a half later and started 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 and harder for existing pop singers to do well commercially. Nevertheless, Bennett continued to enjoy success, placing eight songs in the Billboard during the latter part of the 1950s, with "In the Middle of an Island" reaching the highest at #9 in 1957.

For a month in August—September 1956, Bennett hosted a NBC Saturday night television variety show,called The Tony Bennett Show, as a summer replacement for The Perry Como Show. Patti Page and Julius La Rosa had in turn hosted the two previous months, and they all shared the same singers, dancers, and orchestra. In 1959, Bennett would again fill in for The Perry Como Show, this time alongside Teresa Brewer and Jaye P. Morgan as co-hosts of the summer-long Perry Presents.

In 1954, the guitarist Chuck Wayne became Bennett's musical director. Bennett released his first long-playing album in 1955, Cloud 7. The album was billed as featuring Wayne and showed Benett's leanings towards jazz. In 1957, Ralph Sharon became Bennett's pianist and musical director, replacing Wayne. 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 The 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 Camero, 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! (1959) were the well-regarded fruits of this collaboration, with "Chicago" being one of the standout songs.

Bennett also built up the quality, and therefore, the reputation of his nightclub act; in this he was following the path of Sinatra and other top jazz and standards singers of this era. In June 1962, Bennett staged a highly-promoted concert performance at Carnegie Hall, using a stellar line-up 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, further cementing Bennett's reputation as a star both at home and abroad. Bennett also appeared on television, and in October 1962 he sang on the first night of the Johnny Carson The Tonight Show.

Also in 1962, Bennett released the song "I Left My Heart in San Francisco". Although this only reached #19 on the , it spent close to a year on various other charts and increased Bennett's exposure. The album of the same title was a 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. Over the years, this 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 of the pop singles chart along with the 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 poorly received 1966 film The Oscar met with middling reviews for Bennett; he did not enjoy the experience and did not seek further roles.

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.

Ralph 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! (1970), before which Bennett became physically ill at the thought of recording. It featured misguided attempts at Beatles and other current songs and a ludicrous psychedelic art 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 Bennett's spending too much time on the road, among other factors. In 1971, their divorce became official. Bennett had been involved with aspiring actress Sandra Grant since filming The Oscar, and on December 29, 1971 they married. They had two daughters, Joanna (born around 1969) and Antonia (born 1974), and moved to Los Angeles.

Taking matters into his own hands, 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 Improv lacked a distribution arrangement with a major label and by 1977 it was out of business. A stint 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 completely separate in 1979, but not officially divorce until 2007). He had 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-fatal 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 tremendous musical talent but was having trouble sustaining a career from it and had little financial sense. 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 theaters to get him away from a "Vegas" image. After some effort, a successful plan to pay back the IRS debt was put into place. Tony Bennett had also 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.

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 regularly book his father on a show with a younger, hip audience, Late Night with David Letterman. This was subsequently followed by appearances on Late Night with Conan O'Brien, The Simpsons, and various MTV programs. In 1993, Bennett played a series of benefit concerts organized by alternative rock radio stations around the country. 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 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 Grammys for Best Traditional Pop Vocal Performance (Bennett's first Grammys 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. (He quipped famously on the show, "I've been unplugged my whole career.") 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 Tony Bennett 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.

Tony Bennett's career as a painter, done under his real name of Benedetto, 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.

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, including one for their 50th anniversary. His painting "Homage to Hockney" (for his friend David Hockney, painted after Hockney drew him) is on permanent display at the highly regarded Butler Institute of American Art in Youngstown, Ohio. His "Boy on Sailboat, Sydney Bay" is in the permanent collection at the National Arts Club in Gramercy Park in New York, as is his "Central Park" at the Smithsonian American Art Museum in Washington, D.C. His paintings and drawings have been featured in ARTnews and other magazines, and sell for as much as $80,000 apiece. Many of his works were published in the art book Tony Bennett: What My Heart Has Seen in 1996. In 2007, another book involving his paintings, Tony Bennett in the Studio: A Life of Art & Music, became a best-seller among art books.

Since his comeback, Bennett has financially prospered; by 1999, his assets were worth $15 to 20 million. He had no intention of retiring, saying "If you study the masters — Picasso, Jack Benny, Fred Astaire — right up to the day they died, they were performing. If you are creative, you get busier as you get older." Indeed, Bennett has continued to record and tour steadily, doing 100 to 200 shows a year. 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 popular Live By Request series, for which he won an Emmy Award. 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. Bennett also published The Good Life: The Autobiography of Tony Bennett in 1998.

A series of albums, often based on themes (Duke Ellington, Louis Armstrong, Billie Holiday, blues, duets) has met with good acceptance; Bennett has won seven more Best Traditional Pop Vocal Performance or Best Traditional Pop Vocal Album Grammys in the subsequent years, most recently for the year 2006. Bennett has sold over 50 million records worldwide during his career.

Accolades came to Bennett. For his contribution to the recording industry, Tony Bennett was given 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, was awarded the Grammy Lifetime Achievement Award in 2001, and 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". On December 4, 2005, Bennett was the recipient of a Kennedy Center Honor. Later, a theatrical musical revue of his songs, called I Left My Heart: A Salute to the Music of Tony Bennett was created and featured some of his best-known songs such as "I Left My Heart in San Francisco", "Because of You", and "Wonderful". The following year, Bennett was inducted into the Long Island Music Hall of Fame.

Bennett frequently donates his time to charitable causes, to the extent that he is sometimes nicknamed "Tony Benefit". In April 2002, he joined Michael Jackson, Chris Tucker and former President Bill Clinton in a fundraiser for the Democratic National Committee at New York's Apollo Theater. He has also recorded public service announcements for Civitan International. In the late 1980s, Bennett entered into a long-term romantic relationship with Susan Crow (born c. 1960), a former New York City schoolteacher. Together they founded Exploring the Arts, a charitable organization dedicated to creating, promoting, and supporting arts education. At the same time 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 and would have a very high graduation rate. 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.

In August 2006, Bennett turned eighty years old. The birthday itself was an occasion for publicity, which then extended through the rest of the following year. An American Classic reached the highest place ever on the albums chart for an album by Bennett and garnered two Grammy Awards; concerts were given, including a high-profile one for New York radio station WLTW-FM; a performance was done with Christina Aguilera and a comedy sketch was made with affectionate Bennett impressionist Alec Baldwin on Saturday Night Live; a Thanksgiving-time, Rob Marshall-directed television special Tony Bennett: An American Classic on NBC, which would win multiple Emmy Awards; receipt of the Billboard Century Award; and guest-mentoring on American Idol season 6 as well as performing during its finale. He received the United Nations High Commissioner for Refugees' Humanitarian Award. Bennett was awarded the National Endowment for the Arts Jazz Masters Award in 2006, the highest honor that the United States bestows upon jazz musicians.

On June 21, 2007, Bennett married long-time girlfriend Susan Crow in a private civil ceremony in New York that was witnessed by former Governor Mario Cuomo.

The year 2008 saw Bennett making two appearances on "New York State of Mind" with Billy Joel at the final concerts given at Shea Stadium, and in October releasing the album A Swingin' Christmas with The Count Basie Big Band, for which he made a number of promotional appearances at holiday time. In 2009, Bennett performed at the conclusion of the final Macworld Conference & Expo for Apple Inc., singing the "The Best Is Yet to Come" and "I Left My Heart In San Francisco" to a standing ovation, and later making his Jazz Fest debut in New Orleans. In February 2010, Bennett was one of over 70 artists singing on "25 for Haiti", a charity single in aid of the 2010 Haiti earthquake.

Bennett has won fifteen Grammy Awards, as follows (years shown are the year in which the ceremony was held and the award was given, not the year in which the recording was released):

• Best Solo Vocal Performance, Male, 1963, "I Left My Heart in San Francisco"
• Record of the Year, 1963, "I Left My Heart in San Francisco"
• Best Traditional Pop Vocal Performance, 1993, Perfectly Frank
• Best Traditional Pop Vocal Performance, 1994, Steppin' Out
• Best Traditional Pop Vocal Performance, 1995, Tony Bennett
• Album of the Year, 1995, Tony Bennett
• Best Traditional Pop Vocal Performance, 1997, Here's to the Ladies
• Best Traditional Pop Vocal Performance, 1998, Tony Bennett on Holiday
• Best Traditional Pop Vocal Performance, 2000, Hot & Cool
• Lifetime Achievement Award, 2001
• Best Traditional Pop Vocal Album, 2003, Bennett Sings the Blues
• Best Traditional Pop Vocal Album, 2004, A Wonderful World (with k.d. lang)
• Best Traditional Pop Vocal Album, 2006, The Art of Romance
• Best Traditional Pop Vocal Album, 2007, An American Classic
• Best Pop Collaboration with Vocals, 2007, "For Once in My Life" (with Stevie Wonder)

Bennett has won two Emmy Awards, as follows (years shown are the year in which the ceremony was held and the award was given, not the year in which the program aired):

• Primetime Emmy Award for Individual Performance in a Variety or Music Program, 1996, Live by Request
• Primetime Emmy Award for Individual Performance in a Variety or Music Program, 2007, Tony Bennett: An American Classic

Bennett has gained other notable recognition:

• New York City's Bronze Medallion, 1969
• Star on the Hollywood Walk of Fame
• Inducted into the Big Band and Jazz Hall of Fame, 1997
• Lifetime achievement award from the American Society of Composers, Authors, and Publishers, 2002
• Kennedy Center Honoree, 2005
• Inducted into the Long Island Music Hall of Fame
• United Nations High Commissioner for Refugees Humanitarian Award, 2006
• National Endowment for the Arts Jazz Masters Award, 2006

Discography

Bennett has released over 70 albums during his career, with almost all being for Columbia Records. The biggest selling of these in the U.S. have been I Left My Heart in San Francisco, Tony Bennett, and An American Classic, all of which went platinum for shipping one million copies. Eight other albums of his have gone gold in the U.S., including several compilations. Bennett has also charted over 30 singles during his career, with his biggest hits all occurring during the early 1950s and none charting since 1967.

Books

• Bennett, Tony. Tony Bennett: What My Heart Has Seen. Rizzoli, 1996. ISBN 0-8478-1972-8.
• Bennett, Tony, with Will Friedwald. The Good Life: The Autobiography Of Tony Bennett. Pocket Books, 1998. ISBN 0-671-02469-8.
• Bennett, Tony, with Robert Sullivan. Tony Bennett in the Studio: A Life of Art & Music. Sterling Publishing, 2007. ISBN 1402747675.