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.

[9] Bennett 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.

[22] Benedetto ran afoul of a sergeant from the South who disliked the Italian from New York City; heavy doses of KP duty or BAR cleaning resulted.

[9] Based upon a suggestion from a teacher at the American Theatre Wing, 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.

[13] Warned by Miller not to imitate Frank Sinatra[11] (who was just then leaving Columbia), Bennett began his career as a crooner of commercial pop tunes.

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.

[34] 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.

[13] Nevertheless, Bennett continued to enjoy success, placing eight songs in the Billboard Top 40 during the latter part of the 1950s, with "In the Middle of an Island" (which he vehemently hated) reaching the highest at number nine in 1957.

It featured 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.

[13] 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.

[53] At the conclusion of the march, Bennett was driven to the airport by Viola Liuzzo, a mother of five from Detroit, who was murdered later that day by the Ku Klux Klan.

[61] Danny got his father's expenses under control, moved him back to New York City, and began booking him in colleges and small theaters to get him away from a "Vegas" image.

[63] No changes to Tony's formal appearance, singing style, musical accompaniment (The Ralph Sharon Trio or an orchestra), or song choice (generally the Great American Songbook) were necessary or desirable.

"[18] 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).

He had no intention of retiring, saying in reference to masters such as Pablo Picasso, Jack Benny, and Fred Astaire: "right up to the day they died, they were performing.

[69] In 1998, Bennett performed on the final day of a mud-soaked Glastonbury Festival in an immaculate suit and tie,[70] his whole set on this occasion consisting of songs about the weather.

A series of albums, often based on themes (such as Duke Ellington, Louis Armstrong, Billie Holiday, blues, or duets), met with largely positive reviews.

[76] 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 City's Apollo Theater.

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.

[13] 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;[36] receipt of the Billboard Century Award;[66] and guest-mentoring on American Idol season 6 as well as performing during its finale.

[79][80] 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,[81][82] and later making his Jazz Fest debut in New Orleans.

[84] 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.

"[86] 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.

He sang duets with seventeen prominent singers of varying techniques, including Aretha Franklin, Willie Nelson, Queen Latifah, and Lady Gaga.

[101] 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.

[119] 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.

[36] Regarding his choices in music, Bennett reiterated his artistic stance in a 2010 interview: I'm not staying contemporary for the big record companies, I don't follow the latest fashions.

The biggest selling of these in the U.S. were I Left My Heart in San Francisco, MTV Unplugged: Tony Bennett, and Duets: An American Classic, all of which went platinum for shipping one million copies.

On February 12, 1952,[148] Bennett married Ohio art student and jazz fan Patricia Beech, whom he had met the previous year after a nightclub performance in Cleveland.