Tony Bennett was the last man standing – the saloon crooner, the jazz interpreter, the subtlest of stylists of the Great American Songbook, the man that Sinatra called the greatest popular singer in the world.
“Your old man takes chances” is what Frank Sinatra told Danny Bennett, Tony’s son and manager. “When others zig, Tony zags,” said Danny. Those risks involved the vocal dynamics of grandeur (no Tony Bennett concert was complete without him shutting down all amplification, singing a cappella without a mic, and rocking the room), of pensive emotional nuance, of a whisper’s near-silence.
With Bennett’s passing on Friday morning at age 96, after his struggle with Alzheimer’s since 2016 and retirement from the stage in 2021, his era of grace and elegance in vocal song is gone. He left a rich, long body of work that will last forever. Choosing 150, let alone 15, of Tony Bennett’s finest musical moments is a tough call to make with early sweeping singles such as “Because of You” and jazzy signatures such as “I Left My Heart in San Francisco.” So Variety has mixed the hits with the rarities in touching on his legendary career.
“Cold Cold Heart” (1951)
Country songwriter Hank Williams had only written and released his melancholy romancer a year before Tony Bennett made it into a smash pop hit. But with its bold-faced vocal clarity and his tear-in-your-beer warble, it’s not hard to hear that an original interpretive singer was on his way up, and that he wore diversity on his sleeve as a song selector.
“Boulevard of Broken Dreams” (1952)
The first track on Bennett’s debut disc for Columbia is a dramatic curiosity — something between a sensuous tango and a schmaltzy show tune as orchestrated by Percy Faith. The Al Dubin/Harry Warren classic allows Bennett to swerve and soar through its tempestuous rhythm with ease and might. Plus, his pointed, quavering recitation of the lyrics “I walk along the street of sorrow /The Boulevard of Broken Dreams / Where gigolo and gigolette / Can take a kiss without regret / So they forget their broken dreams” is killer stuff.
“Rags to Riches” (1953)
Re-watch the opening of Marty Scorsese’s “Goodfellas” right after the blood begins to flow deep and red. Then we’ll talk. Brassy and ballsy.
“Lost in the Stars” (1959)
From “In Person!” (a live album first recorded in mono, then changed to a studio production for stereophonic sound), and with the imaginative accompaniment of the Count Basie Orchestra, Bennett’s poetic reading of Maxwell Anderson and Kurt Weill’s classic is the first opportunity we hear where the crooner ably opens up his intonation to impressionistic atmospheric instrumentation and arrangements. Truly magical.
“The Party’s Over” (1959)
Bennett’s “Hometown, My Town” album is an embarrassment of riches when it comes to dedication to all things New York. Let’s start with the dear and pensive “The Party’s Over” from composers Jule Styne, Betty Comden and Adolph Green’s Judy Holliday musical “Bells Are Ringing.” Bennett takes his time through the lyrics look at dreams, rumination and isolation before its near-finale scat-singing bridge.
“Once Upon a Time” (1962)
How would you like to be the song after “I Left My Heart in San Francisco” on the album of the same name? That is the fate, and joy, of composers Charles Strouse and Lee Adams’ “Once Upon a Time” and Bennett’s graceful, gentle take on love and loss.
“Quiet Nights of Quiet Stars (Corcovado)” (1963)
Bennett was famously revolutionary for bringing the bossa nova and the samba to the not-so-sandy shores of the U.S, and the singer’s warm, drifting interpretation of Antônio Carlos Jobim’s slippery chord changes shows why. Bennett is so tender, tactile and free with his phrasing here – such a pleasure to behold.
“Who Can I Turn To (When Nobody Needs Me)” (1964)
British showtune songwriters Leslie Bricusse and Anthony Newley weren’t known for their subtlety. Yet Bennett and pianist Ralph Sharon strip away any and all rococo folderol to get to the meat of rejection with their spare, cutting (yet still happily hammy) rendition.
“The Shadow of Your Smile (Love Theme from ‘The Sandpiper’)” (1966)
Every musician who saw “The Sandpiper” in the movie theater covered composer-arranger Johnny Mandel’s deceptively complex ballad — Sinatra, Streisand, Mathis. Only Bennett, however, tucks into the supple sadness of Paul Francis Webster’s lyrics and comes out with a tense, sad vocal that breaks ever-so-slightly at a crucial impactful moment of the track.
“Days of Wine and Roses” (1975)
Bennett had a knack for working with some of the most innovative, colorful pianists in pop and jazz. So the entirety of 1975’s “The Tony Bennett/Bill Evans Album” is worth a deep dive. For the sake of singling out one moment, Henry Mancini and Johnny Mercer’s forlorn ballad finds Evans laying down sparse but playful chords for Bennett to romp about freely. By 1975, what made Bennett’s voice truly magnetic was its early stages of gruffness, and with that Tony aged perfectly into the vintage “Wine.”
“The Folks Who Live on the Hill” (1990)
After a long break in album-making, Bennett returned to recording and to crafting tributes to his roots with “Astoria: Portrait of the Artist.” One of the album’s centerpiece’s find Bennett talk-crooning his way through Ralph Sharon’s dancing piano, composer Oscar Hammerstein II’s homey romanticism, and an honest, life-size look at aging.
“Don’t Worry ‘Bout Me” (1992)
During his warm tribute to friend and fellow traveler Frank Sinatra, Bennett — a marvelous curator beyond his singing skills — delves deep into Old Blue Eyes’ canon for a craggy, sung-spoken take on the Koehler/Bloom rare classic with a subdued jazzy backing from pianist Sharon and his orchestra.
“Steppin’ Out” (1993, 1994)
Tony Bennett could cut a rug. Therefore, to allow his love of hoofer Fred Astaire to show through, he recorded an entire album of songs dedicated to the dance master, and began the beguine with this righteously rhythmic entrance from the pen of Irving Berlin. Then, a year later, when he wanted to hep the kids to his dance moves and cool factor, Bennett repeated the thrill of Berlin for his massive “MTV Unplugged” showcase.
“How Do You Keep the Music Playing (Live at the Royal Variety Performance, Great Britain)” (2011)
Initially recorded on 1986’s stunning “The Age of Excellence” album, the song has Bennett waltzing into the late-in-life look at romance and sensuality with gravitas, for sure, but with a sense of play that makes Alan and Marilyn Bergman’s composition come alive like never before.
“Sophisticated Lady” (2014)
Square in the middle of his glorious duets album with Lady Gaga, “Cheek to Cheek,” sits one of Bennett’s superior latter-day vocal soliloquies, “Sophisticated Lady.” With the cosmopolitan complexity of Duke Ellington to guide him, Tony Bennett proved he hadn’t lost a step when it came to jazzily reinterpreting his own signature ease and elegance seven decades since his start.