2006–2021: Later years and final album
On August 3, 2006, Bennett turned 80 years old. His record label celebrated by releasing reissues, compilations, and the album Duets: An American Classic, which reached his highest chart position ever and won a Grammy Award. Concerts were given, including a high-profile one for New York radio station WLTW/106.7; 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 went on to 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.
In 2008, Bennett made two appearances with Billy Joel singing "New York State of Mind" at the final concerts given at Shea Stadium, and in October released 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 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 who sang on "We Are the World 25 for Haiti", a charity single in aid of the 2010 Haiti earthquake. In October, he performed "I Left My Heart in San Francisco" at AT&T Park before the third inning of Game 1 of the 2010 World Series and sang "God Bless America" during the seventh-inning stretch. Days later he sang "America the Beautiful" at the Rally to Restore Sanity and/or Fear in Washington, D.C., which he reprised ten years later in a segment on The Late Show with Stephen Colbert.
In September 2011, Bennett appeared on The Howard Stern Show and named American military actions in the Middle East as the root cause of the September 11 attacks. Bennett also claimed that former President George W. Bush personally told him at the Kennedy Center in December 2005 that he felt he had made a mistake invading Iraq, to which a Bush spokesperson replied, "This account is flatly wrong." Following bad press resulting from his remarks, Bennett clarified his position, writing: "There is simply no excuse for terrorism and the murder 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 life-long humanist and pacifist, and reinforced my belief that violence begets violence and that war is the lowest form of human behavior."
In September 2011, Bennett released Duets II, a follow-up to his first collaboration album, in conjunction with his 85th birthday. He sang duets with seventeen prominent singers of varying techniques, including Aretha Franklin, Willie Nelson, Queen Latifah, and Lady Gaga. Bennett appeared on the season 2 premiere of the television procedural Blue Bloods performing "It Had To Be You" with Carrie Underwood. His duet with Amy Winehouse on "Body and Soul"—reportedly the last recording she made before her death—charted on the lower reaches of the Billboard Hot 100, making Bennett the oldest living artist to appear there, as well as the artist with the greatest span of appearances. The single did well in Europe, where it reached the top 15 in several countries. The album then debuted at number one on the Billboard 200, making Bennett the oldest living artist to reach that top spot, as well as marking the first time he had reached it himself. A model of Koss headphones, the Tony Bennett Signature Edition (TBSE1), was created for this milestone (Bennett having been one of the early adopters of the Koss product back in the 1960s). In November 2011, Columbia released Tony Bennett – The Complete Collection, a 73-CD plus 3-DVD set, which although not absolutely "complete", finally brought forth many albums that had not had a previous CD release, as well as some unreleased material and rarities. In December 2011, Bennett appeared at the Royal Variety Performance in Salford in the presence of Princess Anne.
In the wake of the premature deaths of Winehouse and Whitney Houston, Bennett called for the legalization of drugs in February 2012. In October 2012, Bennett released Viva Duets, an album of Latin American music duets, featuring Vicente Fernández, Juan Luis Guerra, and Vicentico among others. The recording and filming for the project, in Fort Lauderdale, was co-sponsored by the city. On October 31, 2012, Bennett performed "I Left My Heart in San Francisco" in front of more than 100,000 fans at a City Hall ceremony commemorating the 2012 World Series victory by the San Francisco Giants. He published another memoir, Life is a Gift: The Zen of Bennett, and a documentary film produced by his son Danny was released, also titled The Zen of Bennett.
In September 2014, Bennett performed for the first time in Israel, with his jazz quartet at the Charles Bronfman Auditorium in Tel Aviv, receiving a standing ovation. He also made a surprise cameo appearance on stage with Lady Gaga at Yarkon Park, Tel Aviv, the previous evening. The performance took place days before the release that month of the two stars' much-delayed collaborative effort and resultant Grammy-winning album, Cheek to Cheek, which debuted at number one on the Billboard charts, extending the 88-year-old Bennett's record for the oldest artist to do so, It also earned him the Guinness World Records for "oldest person to reach No.1 on the US Album Chart with a newly recorded album", at the age of 88 years and 69 days. In October 2014, Bennett and Lady Gaga released the concert special Tony Bennett and Lady Gaga: Cheek to Cheek Live!, and at the end of the year, they kicked off their co-headlining Cheek to Cheek Tour. The pair also appeared in a Barnes & Noble commercial.
On September 25, 2015, he released an album of songs composed by Jerome Kern, featuring Bill Charlap on piano, called The Silver Lining: The Songs of Jerome Kern. On November 1, 2015, Bennett, joined by the choir from the Frank Sinatra School, sang "America the Beautiful" before Game 5 of the baseball World Series between the Kansas City Royals and New York Mets at Citi Field.
On August 19, 2016, shortly after his 90th birthday, Bennett was honored by the unveiling of an 8-foot tall statue in his likeness in front of the Fairmont Hotel in San Francisco. With Senator Dianne Feinstein, House Minority Leader Nancy Pelosi, and several San Francisco mayors in attendance, Bennett was serenaded by a young-adult choir singing "I Left My Heart in San Francisco". Bennett had first sung the song at the hotel in 1961. That same year, he performed at the Macy's Thanksgiving Day Parade on November 24 and the Rockefeller Center tree lighting on November 30. On December 20, 2016, NBC televised a special concert in honor of his 90th birthday, called Tony Bennett Celebrates 90: The Best Is Yet to Come. In September 2018, Bennett re-recorded the George Gershwin song "Fascinating Rhythm", after 68 years and 342 days, according to the Guinness World Records adjudicator, earning the title of "longest time between the release of an original recording and a re-recording of the same single by the same artist". The song appeared on the collaborative album Love Is Here to Stay with Diana Krall that was released on September 14.
Bennett's final album, Love for Sale, another collaborative record with Lady Gaga, was released on September 30, 2021. The record received generally favorable reviews, and debuted at number eight in the United States. Alexis Petridis called Bennett's performance on the album "pretty remarkable", despite the singer's age and health condition, in his review for The Guardian. Bennett broke the individual record for the longest span of top-10 albums on the Billboard 200 chart for any living artist; his first top-10 record was I Left My Heart in San Francisco in 1962. Bennett also broke the Guinness World Record for the oldest person to release an album of new material, at the age of 95 years and 60 days until being surpassed by saxophonist Marshall Allen at age 100 on February 14, 2025.
Bennett's final live performances were on August 3 and 5, 2021, when he presented a pair of shows with Lady Gaga at Radio City Music Hall. On August 12, 2021, nine days after his 95th birthday, Bennett's retirement from concerts was announced by his son and manager Danny Bennett. Danny stated that though his father remained a capable singer, he was becoming physically frail and risked a major fall if he continued touring. A television special, One Last Time: An Evening with Tony Bennett and Lady Gaga debuted on November 28, 2021, on CBS, which contained select performances from the two final concerts. Bennett's last televised performance was also with Gaga on December 16, 2021, on MTV Unplugged. The special was filmed the previous July in front of an intimate studio audience in New York City, and included duets from Love for Sale.
Despite his retirement, as of early 2022, Bennett still continued to rehearse with his music director three times a week, Danny Bennett said in an interview.
