The last of the great saloon singers of the mid-20th century, Bennett often said his lifelong ambition was to create “a hit catalog rather than hit records.” He released more than 70 albums, bringing him 19 competitive Grammys — all but two after he reached his 60s — and enjoyed deep and lasting affection from fans and fellow artists.
Bennett didn’t tell his own story when performing; he let the music speak instead — the Gershwins and Cole Porter, Irving Berlin and Jerome Kern. Unlike his friend and mentor Sinatra, he would interpret a song rather than embody it. If his singing and public life lacked the high drama of Sinatra’s, Bennett appealed with an easy, courtly manner and an uncommonly rich and durable voice — “A tenor who sings like a baritone,” he called himself — that made him a master of caressing a ballad or brightening an up-tempo number.
Bennett was praised often by his peers, but never more meaningfully than by what Sinatra said in a 1965 Life magazine interview: “For my money, Tony Bennett is the best singer in the business. He excites me when I watch him. He moves me. He’s the singer who gets across what the composer has in mind, and probably a little more.”
Ironically, his most famous contribution came through two unknowns, George Cory and Douglass Cross, who in the early ’60s provided Bennett with his signature song at a time his career was in a lull. They gave Bennett’s musical director, pianist Ralph Sharon, some sheet music that he stuck in a dresser drawer and forgot about until he was packing for a tour that included a stop in San Francisco.
“Ralph saw some sheet music in his shirt drawer … and on top of the pile was a song called ‘I Left My Heart In San Francisco.’ Ralph thought it would be good material for San Francisco,” Bennett said. “We were rehearsing and the bartender in the club in Little Rock, Arkansas, said, ‘If you record that song, I’m going to be the first to buy it.’”
By his early 40s, he was seemingly out of fashion. But after turning 60, an age when even the most popular artists often settle for just pleasing their older fans, Bennett and his son and manager, Danny, found creative ways to market the singer to the MTV Generation. He made guest appearances on “Late Night with David Letterman” and became a celebrity guest artist on “The Simpsons.” He wore a black T-shirt and sunglasses as a presenter with the Red Hot Chili Peppers at the 1993 MTV Music Video Awards, and his own video of “Steppin’ Out With My Baby” from his Grammy-winning Fred Astaire tribute album ended up on MTV’s hip “Buzz Bin.”
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