Danny Bennett, a son from Bennett’s first marriage, became his personal manager and engineered his father’s comeback and his return to Columbia. 1986’s The Art of Excellence was Bennett’s first album to reach the pop charts in 14 years. It began a spectacular string of critically-acclaimed and best-selling recordings that celebrated musical heroes (among them Bennett/Berlin, Perfectly Frank and Steppin’ Out, featuring songs popularized by dancer Fred Astaire, Bennett Sings Ellington: Hot and Cool and Here’s to the Ladies) .

In 2014, Cheek to Cheek, a collection of standards that paired Bennett and Lady Gaga, debuted at No. 1 on Billboard’s Top 200 pop and rock chart. The subsequent PBS special was nominated for an Emmy. In his ninth decade, Bennett sold a reported 10 million albums.

Bennett, to paraphrase the title of his idol Frank Sinatra’s own signature song, did it his way. When he appeared on MTV Unplugged, guest artists such as k.d. lang and Elvis Costello dueted on songs from Bennett’s vast repertoire of standards, and not the other way around. He played intimate clubs and the finest concert halls rather than impersonal stadiums.

It was a testament to his cross-generational appeal that he appeared on American Idol, voiced himself on The Simpsons, made a self-deprecating cameo opposite a Bennett-impersonating Alec Baldwin on Saturday Night Live and guested on The Howard Stern Show and Late Night with David Letterman

Danny Bennett booked him with alternative acts like the Red Hot Chili Peppers and the Lemonheads. “He told me that he deplores the notion of demographics,” Danny told The Chicago Tribune in 1994. “So I knew it was a matter of turning the market around. Instead of fitting the artist to the marketing, I fit the marketing to the artist.”

Bennett was a champion of the arts. He co-founded Exploring the Arts (ETA) with his third wife, Susan Crow, a Tony Bennett fan club member who met Bennett backstage when she was 19. ETA supports public school arts education. One of ETA’s first initiatives was the Frank Sinatra School of the Arts, a public school which opened in New York City in 2009. 

Bennett was also a recognized painter, whose works are in the Smithsonian collections as well as the Butler Institute in Youngstown, OH. The 2007 book, Tony Bennett in the Studio: A Life of Art and Music, features 200 of his works. He took up sculpting at the age of 85. 

In addition to his memoir, Bennett also wrote two collections of anecdotes and life lessons, Life is a Gift in 2012 and Just Getting Started in 2016. But he was an Oscar short of an EGOT. His acting career began and ended with The Oscar, a 1966 critical and box office flop now considered something of a camp classic, and which handed Bennett such cringeworthy dialogue as, “Like a junkie shooting pure quicksilver into his veins, Frankie got turned on by the wildest narcotic known to man: success!”

Bennett continued to record as well as tour after he was diagnosed in 2016 with Alzheimer’s. Antonia Bennett, his daughter from his second marriage (that union dissolved in 2007), opened his shows. A second collection of duets he recorded with Lady Gaga between 2018-2020 was scheduled for release in the spring of this year. Bennett’s family revealed the singer’s condition in a February 2021 AARP profile.

Latter-year profiles of Bennett that were written without knowledge of his Alzheimer’s diagnosis make for poignant reading. “Tony’s all about moving forward,” Danny Bennett said in the 2017 New York Times article. “He tells me, ‘Hey, as long as my voice doesn’t wobble and people like me, I’m going to keep singing until I die.’”

Bennett himself is quoted in the piece too: “I could have retired 16 years ago, but I just love what I’m doing.”

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