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Celebrating Tony Bennett on what would have been his 100th birthday

DAVID BIANCULLI, HOST:

This is FRESH AIR. Monday marks the centennial of the birth of singer Anthony Benedetto . Early patron Bob Hope suggested he anglicize his stage name to Tony Bennett. A lifelong New Yorker, Bennett had a long series of hits starting in the 1950s. In 1965, Bennett marched on Selma with Martin Luther King Jr. Later, he became a successful painter of portraits, landscapes and cityscapes. He then had a spectacular late-career comeback, recording scores of vocal duets. Tony Bennett's hits include "Rags To Riches," "I Wanna Be Around" and "I Left My Heart In San Francisco." Jazz historian Kevin Whitehead offers an appreciation, which includes some of Bennett's lesser-known songs.

(SOUNDBITE OF SONG, "OUT OF THIS WORLD")

TONY BENNETT: (Singing) You're clear out of this world. When I'm looking at you, I hear out of this world. The music that no mortal ever knew.

KEVIN WHITEHEAD, BYLINE: Tony Bennett, 1964, with saxophonist Stan Getz, pianist Herbie Hancock, bassist Ron Carter and drummer Elvin Jones - fast company. The song is "Out Of This World" by one of Bennett's favorite composers, Harold Arlen. Tony Bennett didn't call himself a jazz singer, but the influence was hard to miss in his swinging paraphrases of a tune. He had one of the great pop singer voices - soaring, confident, big as a billboard. He liked a big finish. Even his vulnerability sounded self-assured, but good taste and timing would save him. Still, on early singles, he might battle top-heavy orchestrations and gimmicky effects, like the tango beat plus castanets that paint a Latin setting on "Boulevard Of Broken Dreams."

(SOUNDBITE OF SONG, "THE BOULEVARD OF BROKEN DREAMS")

BENNETT: (Singing) Here is where you'll always find me, always walking up and down. But I left my soul behind me in an old cathedral town. The joy that you find here, you borrow. You cannot keep it long it seems. But Gigolo and Gigolette still sing a song and dance along the boulevard of broken dreams.

WHITEHEAD: When Tony Bennett was getting started in the late 1940s, early booster Pearl Bailey warned him learning proper stagecraft takes 10 years. He got there about on schedule. Bennett's favorite jazz composer was Duke Ellington, but his favorite band leader was Count Basie, whose orchestra he recorded with in 1958. Basie's fireworks in that period fit a singer who liked to go big.

(SOUNDBITE OF SONG, "TAKING A CHANCE ON LOVE")

BENNETT: (Singing) Things are mending now. I see a rainbow blending now. We'll have a happy ending now. We're taking a chance. I hear the trumpets blow again. And we're taking a chance. About to take that ride again. Taking a chance.

WHITEHEAD: In the early '60s, Tony Bennett had his signature hit "I Left My Heart In San Francisco" and made some good jazzy records. But as rock music took over, he came to stand for a fading breed, guy in a tux with a loosened tie singing Cole Porter in a Vegas lounge. Bennett ignored advice to modernize and kept on going. In the '70s, he downsized, had his own small label and recorded some of his most intimate sessions in duo with pianist Bill Evans, and with a quartet run by Ruby Braff on cornet and George Barnes on guitar. On ballads, the singer kept his power in reserve.

(SOUNDBITE OF SONG, "ISN'T IT ROMANTIC")

BENNETT: (Singing) Isn't it romantic, merely to be young on such a night as this? Isn't it romantic? Every note that's sung is like a lover's kiss. Sweet symbols in the moonlight. Do you mean that I will fall in love perchance? Isn't it romance?

WHITEHEAD: In 1980, Tony Bennett's career was in a slump. Things began turning around when his son Danny became his manager, introducing him to younger listeners via MTV and late-night television shows. The CD reissue boom helped. Folks heard Tony's old sides with fresh ears or for the first time. And he made a few records with his working trio, where we could hear how expertly his longtime pianist Ralph Sharon shepherds him along.

BENNETT: (Singing) I took a trip on a train, and I thought about you. I passed a shadowy lane, and I thought about you. Two or three cars parked under the stars, a windin' stream. Moon shining down on some little town, and with each beam, the same old dream.

WHITEHEAD: In his last phase, Tony Bennett famously recorded many, many duets with diverse singers - B.B. King, Bonnie Raitt, Barbra Streisand, Bono, Billy Joel, Michael Buble. That's just some of the B's. The series got rolling in the '90s when he paired up with k.d. lang, a very good fit. Here they are in 2001.

(SOUNDBITE OF SONG, "KEEP THE FAITH, BABY")

BENNETT: (Singing) I'll go on.

K D LANG: (Singing) I'll go on.

BENNETT: (Singing) I'll go on.

LANG: (Singing) Go on.

BENNETT: (Singing) I'll go on and...

TONY BENNETT AND K D LANG: (Singing) Do my best.

LANG: (Singing) I'll go on. I'll go on. I'll go on and never rest.

BENNETT: (Singing) Keep the faith. Keep the faith.

LANG: I will.

BENNETT: (Singing) Keep the faith, (laughter) baby. Oh, yes.

WHITEHEAD: That fake little laugh - he used that a lot. Tony Bennett's late duets cast a wide net. Some are quite good. Others, not so much. The rock 'em, sock 'em swingers with Lady Gaga lean hard on the old Vegas glitz, as if to vindicate the 1960s Tony the hippies ignored. At least all the attention the duets brought him let Bennett see that in the long run, everybody loved him just as he was. Tony Bennett sang as long as he was able, last performing in 2021, on turning 95. He died less than two years later. He had a voice you can recognize anywhere. A singer can't do much better than that.

(SOUNDBITE OF SONG, "DANCING IN THE DARK")

BENNETT: (Singing) Dancing in the dark till the tune ends. We're dancing in the dark, and it soon ends. We're waltzing in the wonder of why we're here.

BIANCULLI: Jazz historian Kevin Whitehead is the author of the books "Why Jazz?," "Play the Way You Feel: The Essential Guide To Jazz Stories On Film" and "New Dutch Swing." Singer Tony Bennett died in 2023 at the age of 96. Monday is the hundredth anniversary of Bennett's birth. Coming up, Justin Chang reviews "I Want Your Sex, " the new comedy film from Olivia Wilde. This is FRESH AIR. Transcript provided by NPR, Copyright NPR.

NPR transcripts are created on a rush deadline by an NPR contractor. This text may not be in its final form and may be updated or revised in the future. Accuracy and availability may vary. The authoritative record of NPR’s programming is the audio record.

Kevin Whitehead is the jazz critic for NPR's Fresh Air with Terry Gross. Currently he reviews for The Audio Beat and Point of Departure.