Sad news hit this morning that Tony Bennett has died following a long battle with Alzheimer’s. The legendary crooner had one of the longest careers in the history of popular music. His debut LP, Because of You, landed in 1952, and he worked steadily in the studio and on the road until 2021.
Fans who came of age in the Fifties will likely remember early hits like “Cold, Cold Heart,” ” Rags to Riches,” and “Strangers in Paradise.” Children of the Sixties are more likely to think of songs like “I Left My Heart in San Francisco,” “I Wanna Be Around,” and “The Good Life.” He struggled to find his footing in the aftermath of the British Invasion, but he continued to headline big shows in Las Vegas. In the Seventies, he teamed up with jazz pianist Bill Evans for a pair of albums.
His career took an unexpected upswing in the late Eighties, when his son Danny Bennett took over as his manager. He got booked on shows like Late Night with David Letterman, The Simpsons, Late Night with Conan O’Brien, and even the MTV Video Music Awards. It created this new persona for Bennett as the hip grandfather of pop music, and he started playing to larger and larger crowds.
Bennett’s grunge-era comeback peaked in 1994, when he released an MTV Unplugged special, featuring guest appearances by k.d. Lang and Elvis Costello. His performance of “Steppin’ Out With My Baby” was put into rotation on the network as a video. Bennett was 68 years old at this point. This was a cover of an Irving Berlin song from 1948. Little effort was made to modernize it for a young audience. And yet there it was, playing alongside videos for Weezer’s “Undone (The Sweater Song),” Green Day’s “Basket Case,” and Sheryl Crow’s “All I Wanna Do.”
Bennett’s Unplugged album won Album of the Year at the 1995 Grammys, beating recent works by Eric Clapton, Bonnie Raitt, Seal, and the Four Tenors. Bennett looked genuinely stunned when his name was read that night. “I don’t believe this,” he said. “I really don’t believe it. This is the greatest moment in my whole musical career, and the greatest moment in my life. I want to thank you very, very much for voting for me. I love being with all of you. There are no words. It’s such a victorious feeling to sing good American music and have this happen. Thank you very much.”
It felt like the capstone moment of his career, but Bennett still had 27 years of creating music in front of him. It’s very hard to imagine that the musical world will see anyone quite like him ever again.