Tony Bennett

At 96 years old, Tony Bennett has this physical status:

Anthony Dominick Benedetto (born August 3, 1926), known professionally as Tony Bennett, is an American singer of traditional pop standards, big band, show tunes, and jazz.

He is also a painter, having created works under the name Anthony Benedetto that are on permanent public display in several institutions.

He is the founder of the Frank Sinatra School of the Arts in Astoria, Queens, New York.Born and raised in Astoria to an Italian-American family, Bennett began singing at an early age.

He fought in the final stages of World War II as a U.S. Army infantryman in the European Theater.

Afterward, he developed his singing technique, signed with Columbia Records and had his first number-one popular song with "Because of You" in 1951.

Several top hits such as "Rags to Riches" followed in early 1953.

He then refined his approach to encompass jazz singing.

He reached an artistic peak in the late 1950s with albums such as The Beat of My Heart and Basie Swings, Bennett Sings.

In 1962, Bennett recorded his signature song, "I Left My Heart in San Francisco".

His career and personal life experienced an extended downturn during the height of the rock music era. Bennett staged a comeback in the late 1980s and 1990s, putting out gold record albums again and expanding his reach to the MTV generation while keeping his musical style intact.

He remains a popular and critically praised recording artist and concert performer in the 2010s.

He has won 19 Grammy Awards (including a Lifetime Achievement Award, presented in 2001) and two Emmy Awards, and was named an NEA Jazz Master and a Kennedy Center Honoree.

Bennett has sold over 50 million records worldwide.

Personal life

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 St. Patrick's Cathedral in Manhattan, New York, in mock mourning. The couple had two sons, D'Andrea (Danny, born 1954) and Daegal (Dae, born 1955). Bennett and his wife Patricia separated in 1965, their marriage a victim of Bennett's spending too much time on the road, among other factors. In 1969, Patricia sued him for divorce on grounds of adultery. In 1971, their divorce became official.

Bennett had become involved with aspiring actress Sandra Grant while filming The Oscar in 1965. The couple lived together for several years and on December 29, 1971, they quietly married in New York. They had two daughters, Joanna (born 1970) and Antonia (born 1974), and moved to Los Angeles. The two were married until 1983.

In the late 1980s, Bennett entered into a long-term romantic relationship with Susan Crow, a former New York City schoolteacher. Susan Marion Crow, born September 9, 1966, is 40 years junior to Tony and had grown up in a family of Bennett fans, and as it happened the singer had once posed with Crow's mother, Marion, while she was pregnant with her. As a teenager, Crow had been the head of the Bay Area fan club for Bennett.

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

In February 2021, an article in AARP Magazine revealed that Bennett was diagnosed with Alzheimer's disease in 2016, though he continued to perform and record until the COVID-19 pandemic in early 2020 (he briefly resumed performing in 2021 for his farewell performances). His twice-weekly singing practices are thought to have kept his brain stimulated and spared him from symptoms such as disorientation, depression and a detachment from reality. His neurologist told AARP that, prior to the pandemic, Bennett's touring schedule "kept him on his toes and also stimulated his brain in a significant way". Bennett had only started showing symptoms of decline in the two years leading up to the article and had continued to record tracks from 2018 to early 2020 with Lady Gaga for their 2021 album Love for Sale, despite at times being "lost and bewildered" during recording sessions. In announcing Bennett's retirement in August 2021, Danny Bennett stated that the Alzheimer's was mainly affecting his short-term memory and that he would often forget he had just performed after a concert; his long-term memory remained intact and he could still fully remember all the lyrics to his repertoire when performing.

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Life and career

Anthony Dominick Benedetto was born in Long Island, Queens, on August 3, 1926. He is the first member of his family to be born in a hospital, and he is the son of grocer John Benedetto and seamstress Anna (Suraci). In 1906, John emigrated from Podargoni, a rural eastern district of Reggio Calabria's southern Italian city of Podargoni. Anna had been born in the United States shortly after her parents had emigrated from the Calabria area in 1899. Other relatives came over as a result of Italy's mass migration to America. Tony grew up in poverty with an older sister, Mary, and an older brother, John Jr. John Sr. instilled in his son a love of art and literature as well as a concern for human suffering, but he died when Tony was ten years old. The child will be a lifelong Democrat after growing up in the Great Depression and a dreadful reflection of Herbert Hoover's presidency would make him a lifelong Democrat.

Bennett grew up listening to Al Jolson, Eddie Cantor, Judy Garland, and Bing Crosby as well as jazz musicians such as Louis Armstrong, Jack Teagarden, and Joe Venuti. Dick's uncle Dick was a tap dancer in vaindeville, giving him a early glimpse of show business, and his uncle Frank was the Queensborough library commissioner. He was already singing and performed at the opening of the Triborough Bridge, standing next to Mayor Fiorello La Guardia, who patted him on the head by age ten. Drawing was another early passion of his; he became known as the nation's best-known caricaturist. 141 and aspire to a life in commercial art. He began singing for hire at the age of 13, appearing as a singing waiter in many Italian restaurants near his native queens.

He attended School of Industrial Art in New York where he studied painting and music and learned how to use proper techniques. However, he dropped out at age 16 to help his family. He served as a copy boy and runner for the Associated Press in Manhattan and several other low-skilled, low-paying jobs. However, he primarily set his sights on a professional singing career, returning to play and winning amateur nights all around the city, and having a fruitful night at a Paramus, New Jersey, nightclub.

During the last stages of World War II, Benedetto was drafted into the United States Army in November 1944. As part of his preparations to become an infantry rifleman, he underwent basic training at Fort Dix and Fort Robinson. Benedetto ran foul of a sergeant from the South who hated the Italian from New York City; large doses of KP duty or BAR cleaning resulted. He was drafted as a replacement infantryman to the 255th Infantry Regiment of the 63rd Infantry Division, a unit serving in the aftermath of the massive losses suffered in the Battle of the Bulge's massive losses. He was processed through the massive Le Havre replacement depot in January 1945. He went from France to Germany later in life. He was on the front line and what he would later describe as a "front-row seat to hell" as March 1945 began.

Benedetto and his company were bitterly combative in cold winter weather, often hunkering down in foxholes as German 88 mm guns fired on them. They crossed the Rhine and into Germany at the end of March, where they were involved in a difficult house-to-house, town-after-town battle to clean out German troops; during the first week of April, they crossed the Kocher River and the Danube by the end of the month. Benedetto barely survived death several times during his time in combat. "Anybody who believes that war is romantic obviously hasn't been through one," the experience made him a pacifist. This isn't life,' I just said.'This isn't it.' "This is not life." At the end of the war, he was involved in the liberation of a Nazi concentration camp near Landsberg, where some American prisoners of war from the 63rd Division had been detained.

Benedetto remained in Germany as part of the occupying army, but he was sent a civilian 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 racially segregated, resulted in his being demoted and reassigned to Graves Registration Service service positions. He performed with the 314th Army Special Services Band under the stage name Joe Bari, which he had begun using before the war and province in Italy, as a partial anagram of his family roots in Calabria). He appeared in several bands that would have gone on to have postwar careers.

Benedetto spent time at the American Theatre Wing on the GI Bill after being discharged from the Army and returning to the United States in 1946. He was taught the bel canto singing discipline, which would keep his voice in good shape for the rest of his career. He continued to excel at whatever level, including at waiting tables. Based on a request from a teacher at American Theatre Wing, he devised an unusual approach that involved imitating, the tone and phrasing of other musicians, including that of Stan Getz's saxophone and Art Tatum's piano, causing him to improvise as he interpret a song. Bari made a few albums as Bari in 1949, but no one else seemed to be selling.

Pearl Bailey noticed Benedetto's talent and begged him to open for her in Greenwich Village in 1949. Bob Hope had been invited to the performance. Hope took Benedetto on the road with him and changed his name to Tony Bennett. Bennett did a demo of "Boulevard of Broken Dreams" in 1950 and was signed by Mitch Miller to the major Columbia Records label.

Bennett began his career as a commercial pop musician, despite Miller's attempt not to imitate Frank Sinatra (who was just leaving Columbia). "Because of You," Miller's first big hit was "Because of You," a Percus Faith ballad with a rich orchestral arrangement. It came out on jukeboxes and then landed at number one on the pop charts in 1951 and remained there for ten weeks, selling over a million copies. This was followed by a similarly styled rendition of Hank Williams' "Cold, Cold Heart," which helped bring Williams and country music in general to a larger, more national audience later this year. The Miller and Faith crew continued to work on all of Bennett's early hits. "Blue Velvet" Bennett's album was also very popular and attracted adoring teenage fans at concerts at the famed Paramount Theatre in New York (Bennett performed seven shows a day beginning at 10:30 a.m.) and elsewhere.

"Rags to Riches" was the third number one in 1953. Unlike Bennett's other early hits, this was an up-tempo big band band with a bold, brassy tone, and a double tango in the instrumental break; it dominated the charts for eight weeks. Bennett's album "Stranger in Paradise" was released later this year as a way to advertise the performance after a New York newspaper strike. Bennett's debut, the show was a hit, and the band began a long tradition of recording show tunes. A year and a half later, Bennett's career as an international artist began, "Stranger in Paradise."

The music industry's dynamic changed as the rock and roll era began in 1955, and it became increasingly difficult for current pop stars to do well commercially. Bennett maintained his popularity, debuting eight songs in the Billboard Top 40 during the second half of the 1950s, with "In the Middle of an Island" (which he vehemently disliked) ranked at number one in 1957.

Bennett appeared on NBC Saturday night as a summer replacement for The Perry Como Show for a month from August to September 1956. Patti Page and Julius La Rosa had performed in turn for the past two months, and they all shared the same singers, dancers, and orchestra. Bennett will appear on The Perry Como Show again in 1959, this time alongside Teresa Brewer and Jaye P. Morgan as co-hosts of the summer-long Perry Presents.

Chuck Wayne, the guitarist, became Bennett's musical director in 1954. In 1955, Bennett released Cloud 7 as his first long-playing album. The album was billed as featuring Wayne Bennett and demonstrating Bennett's leanings toward jazz. Ralph Sharon, Bennett's keyboardist, arranger, and musical director, replacing Wayne, became Bennett's pianist, arranger, and musical director in 1957. Sharon warned Bennett that a career of "sweet saccharine songs like 'Blue Velvet'" would not last long, and that Bennett should rely even more on his jazz interests.

The result was the 1957 album The Beat of My Heart. It featured well-known jazz artists, including Herbie Mann and Nat Adderley, with a strong emphasis on percussion from Art Blakey, Jo Jones, Latin artist Candido Camero, and Chico Hamilton. Both popular and critically praised the album. Bennett continued his success by playing with the Count Basie Orchestra, becoming the first male pop vocalist to perform with Basie's band. Basie Swings, Bennett Sings (1958) and In Person! (1959) were among the best-known fruits of the pair's collaboration, with "Chicago" being one of the most popular songs.

Bennett also improved the quality and, consequently, the reputation of his nightclub act; in this respect, he was following Sinatra and other top jazz and standards singers of the current period. Bennett staged a highly praised concert performance at Carnegie Hall in June 1962, starring Al Cohn, Kenny Burrell, and Candido, as well as the Ralph Sharon Trio. Until then, Carnegie Hall had not seen a male pop performer (only Judy Garland a year before that). The set featured 44 songs, including favorites like "I've Got the World on a String" and "The Greatest Is Yet To Come" on the program. Bennett's reputation as a leading actor both nationally and abroad was firmly established by the event. Bennett has appeared on television, and in October 1962 he appeared on the first broadcast of The Tonight Show Starring Johnny Carson.

Bennett's collection of "I Left My Heart in San Francisco" was released in 1962, a decade-old but little-known song originally written for an opera singer. Despite being ranked 19 on the Billboard Hot 100, Bennett's exposure soared after the year on various other charts and boosted Bennett's visibility. Both the single and album had gold record success, with the album of the same name being a top-five hit. Bennett's album was nominated for Best Male Vocal Performance and Record of the Year. This will be Bennett's signature song over the years. On an RIAA/NEA list of the twentieth century's most Historical Significant Songs, it ranked 23rd.

Bennett's next album, I Wanna Be Around (1963), was also a top-five hit, with the title track and "The Good Life" both debuting in the top 20 of the pop charts, as well as the top ten of the Adult Contemporary chart.

The Beatles and the British Invasion took place next year, and with them still more musical and cultural interest to rock than to pop, standards, and jazz. Bennett had minor hits with several albums and singles based on show tunes over the next few years, but his commercial success was clearly starting to decline. Bennett's attempt to break into acting in the underrated 1966 film The Oscar recipient received mixed feedback; he did not enjoy the experience and did not seek out further roles.

Bennett, a civil rights activist, was active in the 1965 Selma-to-Montey marches. He would continue this commitment many years later by refusing to participate in apartheid South Africa.

In 1965, Ralph Sharon and Bennett parted ways. Singers such as Lena Horne and Barbra Streisand were encouraged to record "contemporary" rock songs, and Columbia Records' Clive Davis recommended that Bennett do the same. Bennett was extremely hesitant, and no one was joking about the results when he tried. Tony Sings of The Great Hits of Today exemplified all of this. Bennett died at the thought of recording (1970), long before he became physically ill at the thought of recording. It also included covers of Beatles and other current songs as well as a psychedelic art cover.

Bennett would recall his surprise at being asked to produce new stuff years later, compared to when his mother was coerced to produce a cheap dress. He had left Columbia for MGM Records (Philips in the United Kingdom) and had relocated to London, where he hosted a television show from the Talk of the Town nightclub in conjunction with Thames Television, Tony Bennett at the Talk of the Town. He tried a number of approaches, including some more Beatles songs, but no new market success was found, and he was without a recording deal for a few years.

Bennett formed Improv, Bennett's own record company, taking matters into his own hands. "What Is This Thing Called Love," he performed some songs that would later become hits, such as "What is This Thing Called Love." "I made two well-received albums with jazz pianist Bill Evans, The Tony Bennett/Bill Evans Album (1975) and Together Again (1976), but Improv was out of business by 1977, and it was out of business."

Bennett had no recording deal, no boss, and no shows outside of Las Vegas as the decade came to an end. He had a heroin use, was living beyond his means, and had the Internal Revenue Service attempting to locate his Los Angeles home.

Bennett's sons Danny and Dae asked for assistance after a near-fatal cocaine overdose in 1979. They were "look, I'm lost here," he told them. "People don't want to hear the music I make."

Danny Bennett, an aspiring musician himself, came to a realization. Danny and his brother's band, Quacky Duck and His Barnyard Friends, had formed, but Danny's musical abilities were limited. However, he had discovered during that time that he didn't have a head for company. On the other hand, his father, on the other hand, was an excellent musician but was having trouble sustaining a career in it and had no budget for it. Danny has been hired as the father's boss after his father.

Danny managed to keep his father's spending under control, took him back to New York, and began booking him in colleges and small theaters to get him away from a "Vegas" image. Following an initial setback, a fruitful scheme to pay back the IRS debt was put into place. The singer had previously worked with Ralph Sharon as his pianist and musical director (and would continue with him until Sharon's retirement in 2002). By 1986, Tony Bennett had returned to Columbia Records, this time under creative ownership, and the Art of Excellence had been published. This was his first album to reach the top of the charts since 1972.

The theme song "Life in a Glass" from Henry Mancini's film "That's Life" (1986), sung by Tony Bennett, has been nominated for Best Original Song at the Academy of Music.

If given the opportunity, Danny Bennett predicted that younger audiences who were unfamiliar with his father would respond to his music. No improvements were made to Tony's formal appearance, singing style, musical accompaniment (The Ralph Sharon Trio or an orchestra), or song choice (generally the Great American Songbook). Danny used to book his father on Late Night with David Letterman, which was a show with a younger, "hip" audience. This was followed by appearances on Late Night with Conan O'Brien, The Simpsons, Muppets Tonight, and various MTV shows. Bennett appeared at a number of benefit concerts hosted by alternative rock radio stations around the country in 1993. The scheme worked; as Tony later stated, "I realized that young people had never heard those songs." Cole Porter, Gershwin – they were like, 'Who wrote that?' It was different to them. If you're different, you stand out."

Bennett continued to record, first releasing Astoria: Portrait of the Artist (1990), then promoting specific albums, such as the Socratic tribute to Perfectly Frank (1992) and the Fred Astaire tribute Steppin' Out (1993). Bennett, Jr., gained Grammy Awards for Best Traditional Pop Vocal Performance (Bennett's first Grammy Awards since 1962) and established Bennett as the inheritor of a classic American great's mantle.

Bennett, who appeared on MTV Video Music Awards as Bennett portrayed the age gap, and Flavor Flav, was evidently, as his "Steppin' Out with My Baby" video demolished it, according to The New York Times. He has firmly connected with a younger crowd of people weaned on rock. There have been no compromises, and there have been no compromises."

Bennett's appearance on MTV Unplugged in 1994 brought the new audience to its peak. (I've been unplugged for my entire life, he declared on the program.) Featuring guest appearances by rock and country stars Elvis Costello and k.d. lang (both of whom had a passion for the standards genre) the program attracted a large audience and a lot of media attention. The MTV Unplugged Tony Bennett album received the highest accolades for the third year in a row, as well as the Best Traditional Pop Vocal Performance Grammy Award for the third year in a row.

Bennett has thrived since his comeback; by 1999, his assets were worth $15 to $20 million. He had no intention of retiring, having said of masters like Pablo Picasso, Jack Benny, and Fred Astaire: "right up to the day they died, they were doing." As you get older, you get busier." Bennett continued to record and tour regularly, selling more than 100 shows per year by the 1990s. Bennett often performed one song (usually "Fly Me to the Moon") without any microphone or amplification, demonstrating his vocal projection skills. Tony Bennett's Wonderful World: Live From San Francisco, a PBS special, was made into a PBS special. Bennett also created the concept and appeared in the first episode of A&E Network's famous Live by Request series, for which he received an Emmy Award. Bennett has appeared in films including The Scout, Analyze This, and Bruce Almighty, in addition to numerous television guest appearances.

He made an unexpected yet highly popular appearance on the last day of a mud-soaked Glastonbury in an immaculate suit and tie, his entire set on this occasion consisting of songs about the weather. In 1998, Bennett published The Good Life: Tony Bennett's Autobiography. Bennett has received eleven more Best Traditional Pop Vocal Album Grammys in recent years, the most recent for the year 2022; a series of albums based on themes (such as Duke Ellington, Louis Armstrong, Billie Holiday, blues, or duets). During his career, Bennett has earned more than 50 million dollars around the world.

Accolades came from Bennett. Tony Bennett was made a Hollywood Walk of Fame at 1560 Vine Street in recognition of his contributions to the recording industry. Bennett was inducted into the Big Band and Jazz Hall of Fame in 1997 and received the American Society of Composers, Authors, and Publishers (ASCAP) lifetime achievement award in 2002. Tony Bennett was featured in Q magazine's list of the "50 Bands To See Before You Die" in 2002. Bennett was named recipient of a Kennedy Center Honor on December 4, 2005. "I Left My Heart: A Salute to Tony Bennett's Music" was released later in San Francisco, and it featured some of his best-known songs, "Because of You" and "Wonderful." Bennett was inducted into the Long Island Music Hall of Fame the following year.

Bennett regularly contributes to charitable causes, to the point that he is often referred to as "Tony Benefit" in the media. In April 2002, Michael Jackson, Chris Tucker, and former President Bill Clinton were among a fundraiser for the Democratic National Committee at New York City's Apollo Theater. He has also produced Civitan International public service announcements.

Danny Bennett continues to be Tony Bennett's boss, while Dae Bennett, a recording engineer who has worked on a variety of Tony's projects and founded Bennett Studios in Englewood, New Jersey in 2001, has been fired due to major label deficits combined with skyrocketing overhead. Antonia, Tony's younger daughter, opens shows for her father.

Bennett turned eighty years old in August 2006. The birthday celebrations were a moment for promotion, which then lasted for the remainder of the year. Duets: An American Classic rose to the top position on the albums chart for an album by Bennett, earning two Grammy Awards; a tribute to Empower Bennett's friendship with Antonio Aguilera; and guest-mentoring on American Idol season 6 as well as performing during its finale. He was named the United Nations High Commissioner for Refugees' Humanitarian Award. In 2006, Bennett received the National Endowment for the Arts Jazz Masters Award, the highest award the United States bestowes on jazz musicians.

Bennett appeared on two occasions at Shea Stadium as "New York State of Mind," and the band's album A Swingin' Christmas with The Count Basie Big Band was released in October, with which he made several promotional appearances at holiday time. Bennett appeared at the conclusion of the final Macworld Conference & Expo for Apple Inc. in 2009, singing "The Best Is Yet to Come" and "I Left My Heart To San Francisco" and "I Left My Heart" in a standing ovation and then debuting at New Orleans for the first time in 2009. Bennett appeared on "We Are the World 25 for Haiti," a charity single in aid of the 2010 Haiti earthquake in February 2010. During the seventh-inning stretch, he sang "I Left My Heart in San Francisco" at AT&T Park in October and sang "God Bless America" during the third inning of Game 1 of the 2010 World Series. At the Rally to Restore Sanity and/or Fear in Washington, D.C., days later, he performed "America the Beautiful" and later on "The Late Show with Stephen Colbert" a decade later.

Bennett appeared on The Howard Stern Show in September 2011 and cited American military operations in the Middle East as the root cause of the September 11 attacks. Former President George W. Bush personally told him at the Kennedy Center in December 2005 that he had made a mistake in invading Iraq, to which a Bush spokesperson responded, "This account is clearly inaccurate." Bennett outlined his argument in the wake of poor press surrounding his remarks: "There is simply no excuse for terrorism and the assassination of the nearly 3,000 innocent victims of the 9/11 attacks on our country." My life experiences, ranging from the Battle of the Bulge to marching with Martin Luther King, made me a lifelong humanist and pacifist, and reinforced my belief that violence precedes violence and that war is the lowest form of human behavior."

In September 2011, Bennett unveiled Duets II, a follow-up to his first collaboration album, in connection with his 85th birthday. Aretha Franklin, Willie Nelson, Queen Latifah, and Lady Gaga appear in duets with seventeen well-known singers of varying styles, including Aretha Franklin, Willie Nelson, Queen Latifah, and Lady Gaga. Bennett appeared on the premiere of the television show "It Had To Be You" with Carrie Underwood. Bennett, as well as the artist with the longest number of appearances, appeared on "Body and Soul," the last recording she made before her death. The single did well in Europe, where it ranked in the top 15 in many nations. Bennett was the first living artist to reach the top spot on the Billboard 200 since his debut on the top chart, as well as the first time he had reached the top spot. The Tony Bennett Signature Edition (TBSE1), a replica of Koss headphones, was made for this historic occasion (Bennett was one of the early adopters of the Koss product in the 1960s). Columbia released Tony Bennett – The Complete Collection, a 73-CD plus DVD set, which although not completely "complete," brought out several albums that had never been available before, as well as some unreleased items and rare finds. In December 2011, Bennett appeared at the Royal Variety Performance in Salford in the presence of Princess Anne.

Bennett, in the aftermath of Winehouse and Whitney Houston's premature deaths, called for the legalization of drugs in February 2012. Bennett released Viva Duets, an album of Latin American music duets starring Vicente Fernández, Juan Luis Guerra, and Vicentico, among other things, in October 2012. The city cosponsored the recording and filming of the project in Fort Lauderdale. Bennett performed "I Left My Heart in San Francisco" on October 31, 2012 in front of more than 100,000 viewers at a City Hall celebration in San Francisco a 2012 World Series victory for the San Francisco Giants. He wrote a memoir called Life is a Gift: The Zen of Bennett, his son Danny Bennett's, and a documentary film titled The Zen of Bennett.

Bennett appeared at the Charles Bronfman Auditorium in Tel Aviv in September 2014 for the first time in Israel, receiving a standing ovation. The previous evening, he made a surprise cameo appearance on stage with Lady Gaga at Hayarkon Park, Tel Aviv. The performance took place just days before the pair's long-awaited collaborative effort and resultant Grammy Award-winning album, Cheek to Cheek, debuted at number one on the Billboard charts, extending Bennett's record for the oldest artist to achieve No. 1 on the US Album Chart with a newly released album at age 88 years and 69 days. Bennett and Lady Gaga produced the concert special Tony Bennett and Lady Gaga: Cheek to Cheek Live! in October 2014, and they kicked off their co-headlining Cheek to Cheek Tour at the end of the year. The two children appeared in a Barnes & Noble commercial.

The Silver Lining: The Songs of Jerome Kern was released on September 25, 2015. Bennett performed "America the Beautiful" at Citi Field on November 1, 2015, when the Frank Sinatra School choir performed "America the Beautiful" before Game 5 of the baseball World Series between the Kansas City Royals and the New York Mets.

Bennett was honoured on August 19, 2016, just 90 years after his 90th birthday, by the unveiling of an 8-foot tall statue in his likeness in front of the Fairmont Hotel in San Francisco. Bennett was serenaded by a youth orchestra performing "I Left My Heart in San Francisco" with Senator Dianne Feinstein, House Minority Leader Nancy Pelosi, and several San Francisco mayors in attendance. Bennett performed the song at the hotel for the first time in 1961. He appeared at the Macy's Thanksgiving Day Parade on November 24 and the Rockefeller Center tree lighting on November 30. He was the same year last year. Tony Bennett, the Best Is Yet to Come, NBC televised a special concert on December 20, 2016, in honor of his 90th birthday. According to the Guinness World Records adjudicator, Bennett re-recorded George Gershwin's "Fascinating Rhythm" after 68 years and 342 days, earning the distinction of "the longest time between the launch of an original record and the re-recording of the same song by the same artist." The song appeared on the compilation album Love Is Here to Stay with Diana Krall, which was released on September 14.

Bennett's uncle and boss Danny Bennett announced his resignation from concerts on August 12, 2021, a week after his 95th birthday. Danny said that although his father was still a talented performer, he was getting physically sick and risked a big crash if he kept touring. Love for Sale, his last album collaborating with Lady Gaga, was released on September 30, 2021. The document received mostly critical feedback and debuted at number eight in the United States, and debuted at number eight. Despite Bennett's age and health in his article for The Guardian, Alexis Petridis called his appearance on the album "very impressive." Bennett set a new personal record for the longest number of top-ten albums on the Billboard 200 chart for any living artist; his first top-ten album was I Left My Heart, which was released in 1962 in San Francisco. At the age of 95 years and 60 days, Bennett also set a Guinness World Record for the first person to record an album of new stuff.

Bennet's last live appearances came on August 3 and 5, 2021, when he opened two shows with Lady Gaga at Radio City Music Hall. At CBS, One Last Time: An Evening With Tony Bennett and Lady Gaga debuted on November 28, 2021, which included select excerpts from the two shows. In MTV Unplugged, Bennett's last televised appearance was with Gaga on December 16, 2021. The special was shot in front of an intimate studio audience in New York City and featured duets from Love for Sale. In 2022, The Lady and the Legend, a documentary that will feature video from Bennett and Gaga's two collaborative albums, will be available on In 2022, The Lady and the Legend will be released exclusively on The Lady and the Legend will appear on

Bennett, despite his retirement, continued to rehearse with his music director three times a week, according to Danny Bennett in an interview.

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