Best Sarah Vaughan Songs: 20 Classic Performances From The Divine One

Frank Sinatra once described Sarah Vaughan as “a singer who sings so good, I want to cut my wrist with a dull blade and let her sing me to death.” Although he was joking about Vaughan’s voice’s effect on him, his admiration for her gloriously rich, full-bodied tone with its velour phrasing and tremulous vibrato was wholeheartedly sincere. Nicknamed “Sassy” and often referred to by her devotees as “The Divine One,” Vaughan was a significant vocal pioneer who – via her assimilation of the melodic and rhythmic innovations of the bebop revolution – helped to modernize the art of jazz singing in the post-war era.

Between 1944, when she made her debut recording with a single called “I’ll Wait And Pray,” and 1989 when she entered a recording studio for the last time to appear on her friend, producer Quincy Jones’ Back On The Block LP, Vaughan demonstrated a breathtaking stylistic range. Though her forte was interpreting jazz standards taken from the hallowed pages of The Great American Songbook, her 49-album discography revealed her as an intrepid artist who successfully reinvented herself. In the 1960s and 70s, she stayed relevant by expanding her repertoire with pop, soul, rock, and even classical music, which she did without losing her jazz core or sacrificing her artistic integrity. In her later years, she explored her deep affinity with Brazilian music with 1987’s Sérgio Mendes-produced Brazilian Romance featuring Milton Nascimento.

As Sarah Vaughan’s discography offers such an abundance of riches, the songs we’ve selected for this best of are intended as a broad-stroked introduction, offering an overview of her repertoire designed to encourage a deeper investigation of her back catalog. We’ve blended hit singles with album cuts and signature songs with lesser-known gems to capture Vaughan’s essence. Expect rhapsodic romantic arias, tales of heartbreak, sassy bebop finger-snappers, tasteful pop covers, and sensuous Brazilian excursions.

Buy the best Sarah Vaughan songs on vinyl now.

A Jersey Girl

A native of Newark, New Jersey, Sarah Vaughan was born in 1924. Sharing her guitar-playing carpenter father’s passion for music, she learned to play the piano at age seven while developing her singing voice in the New Mount Zion Baptist Church choir. In her teenage years, Vaughan began performing publicly, quitting school early to focus on developing her fledgling music career. At eighteen, she ventured to Harlem’s famed Apollo Theater for an amateur talent contest, initially as an accompanist to a friend who won second prize. Shortly afterward, Vaughan plucked up the courage to return to the Apollo as a solo singer, winning first prize and $10 for her rendition of the jazz standard “Body & Soul.” That led to a week-long engagement at the theater that saw her open for rising jazz star Ella Fitzgerald.

Her Apollo stint got Vaughan noticed, putting her on the radar of singer Billy Eckstine, then working in the band of the influential jazz pianist Earl “Fatha” Hines. On Eckstine’s recommendation, Hines recruited Vaughan to his band, which included trumpeter Dizzy Gillespie and saxophonist Charlie Parker, the future architects of a new style called bebop. When Eckstine left Hines and formed a progressive big band featuring Gillespie and Parker, Vaughan joined him. The legendary group, which would include future modern jazz pathfinders Art Blakey, Miles Davis, Kenny Dorham, and Dexter Gordon, was crucial in Vaughan’s development as a singer, familiarizing her with the evolving language of bebop, a radically new kind of jazz defined by complex melodies, harmonies and rhythms.

Sassy the hitmaker

Sarah Vaughan’s alliance with Eckstine resulted in her singing on his band’s song “I’ll Wait And Pray,” released in 1945. Shortly afterward, Vaughan cut her first solo recordings for a small company called Continental before joining the Musicraft label, scoring her first US pop hit with “Tenderly,” a soft ballad accompanied by her then manager and first husband George Treadwell’s Orchestra. Showcasing Vaughan’s opulent sound with its flawless, finely calibrated technique, the memorable number – which she re-recorded in 1954 for the Mercury Records album The Divine Sarah Sings – reached No. 27.

An even bigger early Vaughan hit was “Black Coffee,” which rose to No. 13 in 1949. The blues-inflected song quickly became a favorite of other female jazz singers – Peggy Lee recorded a celebrated version in 1953 – but Vaughan had the distinction of putting her stamp on it first.

In 1950, Vaughan hit the US charts again with an upbeat big band number, “(I Love The Girl) I Love The Guy,” which reached No. 10. The spirited track, where her voice rose from a soft melodious contralto purr to a dazzling falsetto, highlighted Vaughan’s three-octave range.

In 1954, Vaughan recorded “Make Yourself Comfortable,” a playful pop song penned by Bob Merrill, famous for writing the novelty song “How Much Is That Doggie In the Window?” Showing a different side of Vaughan and highlighting her versatility, the track hit No. 6 in the US pop chart.

One of Vaughan’s most unexpected hits was 1955’s Latin-flavored “Whatever Lola Wants (Lola Gets),” the first recording of the famous Richard Adler-Jerry Ross tune from the musical Damn Yankees. Driven by a bongo-propelled tango rhythm, the skittish tune – which peaked at No. 6 on the US pop chart – captured Vaughan’s throaty voice at its most creamy and sensuous. In 2003, the track was sensationally given a contemporary makeover by Gotan Project on the album Verve Remixed 2.

Vaughan was also the first artist to record “Broken Hearted Melody,” released as a single in 1959. Her first million-seller and maiden Grammy nomination, the song proved a resounding international success, reaching No. 7 in both the US and the UK charts as well as making waves in Canada, Australia, and the Netherlands. Her immaculate pitch-perfect vocals were supported by male background voices and syrupy string lines over a chugging, guitar-driven backbeat.

The jazz goddess

Although her pop hits in the 1950s took her music to a substantial mainstream audience, at heart, Sarah Vaughan was a committed jazz singer. The late Quincy Jones said of her, “She thought like a horn and sang like a horn,” which were qualities she shared with her peers, Billie Holiday and Ella Fitzgerald, who modeled themselves on saxophone and trumpet players. Vaughan knew how to improvise, which she revealed in passages of her records where she scatted, a technique introduced by Louis Armstrong in the 1920s. As Vaughan vividly demonstrates on “Shulie A Bop,” the bebop-flavored track she co-wrote that appeared as the opener of her classic 1957 album Swingin’ Easy, she was a fluent and imaginative improviser, using her voice as an instrument in the way she extemporized wordless melodies.

From the same album, the achingly slow “Lover Man (Oh, Where Can You Be?)” – first recorded by Billie Holiday in 1945 – offered a stark musical contrast, showing how Vaughan excelled as a ballad singer. Whereas Holiday’s version was haunting and desolate, Vaughan’s is more wistful and sentimental.

Vaughan’s most famous ballad is her indelible take on pianist Erroll Garner’s 1954 classic, “Misty,” which began life as an instrumental before lyricist Johnny Burke contributed words. Pittsburgh jazz singer Dakota Staton recorded the first vocal version in 1957, but it was quickly eclipsed two years later by Vaughan’s voluptuous reading, taken from her album Vaughan And Violins. Recorded in Paris during a European tour, the track exuded a mystical quality thanks to Quincy Jones’ shimmering orchestral arrangement.

No Sarah Vaughan best of would have credibility without the song “My Funny Valentine,” her extraordinary version of a Rodgers and Hart classic from 1937. Illustrating her impeccable vocal control, the tune appeared on her 1955 Mercury album The Divine Sarah.

Another immortal Vaughan performance is provided by her magical vocal rendition of “Lullaby Of Birdland,” a 1952 tune British pianist George Shearing composed to promote the then-newly opened Birdland, a New York jazz club. After lyricist George Weiss wrote words for it, the song was cut by Ella Fitzgerald in 1954, with Vaughan following suit a year later on her self-titled Mercury debut LP.

Adventures in Contemporary Pop

The arrival of long-haired pop and rock groups in the 1960s weakened the commercial appeal of jazz, which had been increasingly marginalized since the explosive rise of rock and roll in the previous decade. Having already proved she was versatile by enjoying 50s pop success, Sarah Vaughan adapted to the changes in musical tastes the 60s brought. Her biggest hit during that decade was a slice of pure pop called “A Lover’s Concerto,” a song based on a J. S. Bach melody produced and arranged by Luchi de Jesus, a Mercury producer who had masterminded pop hits for Brook Benton, Dinah Washington, and Jerry Butler. A big US hit first for R&B trio The Toys in 1965, the track was featured on the 1966 LP, The Pop Artistry Of Sarah Vaughan, and reached No. 5 in the US Adult Contemporary chart. The same album featured Vaughan’s first recording of a Beatles song: Lennon and McCartney’s “Yesterday,” reflecting the “Fab Four’s” growing influence on jazz musicians.

America’s Burt Bacharach and Hal David also profoundly shaped contemporary pop music sensibilities in the 1960s. Vaughan served up a smoldering version of “Alfie,” their Cilla Black movie soundtrack hit, on her 1967 LP It’s A Man’s World.

In the 70s, Vaughan’s stylistic palette widened further with covers of John Lennon, Bob Dylan, and Carly Simon songs on her album A Time In My Life; its chief highlight was a version of soul singer Marvin Gaye’s febrile urban lament “Inner City Blues (Makes Me Wanna Holler),” on which Vaughan showed she possessed an innate feel for funky grooves.

The Collaborations

Sarah Vaughan’s career included several notable collaborations in the recording studio. In 1957, the singer joined forces with her early mentor, resonant-voiced crooner Billy Eckstine to score a US hit single with “Passing Strangers,” a storytelling romantic ballad spotlighting the pair’s tantalizing musical chemistry. That year, they performed it together on The Ed Sullivan Show.

In 1972, Vaughan joined forces with the French jazz pianist and film composer Michel Legrand for the 1972 album Sarah Vaughan With Michel Legrand. The highlight was Vaughan’s interpretation of Legrand’s poignant ballad “The Summer Knows,” in which her rich voice was complemented by lush orchestration.

Vaughan appeared on the same stage as Count Basie but never recorded with him in the studio; she did, however, record with the Count Basie Orchestra minus their leader on three albums. Their third collaboration, 1981’s Send In The Clowns included her indelible performance of the bittersweet Stephen Sondheim-penned title song, which she first recorded with a pop arrangement in 1974. A stunning showcase for Vaughan’s extraordinary vocal gymnastics, the song became the stunning centerpiece of the singer’s late-career live shows.

The Brazilian connection

The 1960s was not only the decade of Beatlemania but also witnessed the rise of the Brazilian bossa nova after Astrud Gilberto scored an international hit with “The Girl From Ipanema.” Like a lot of jazz musicians, Sarah Vaughan immediately took to the bossa nova’s sophisticated melodies and gently syncopated rhythms. “It was her favorite kind of music,” revealed Quincy Jones, who helmed the singer’s 1966 LP, Viva Vaughan, which included three bossa nova tunes, the best of which was “Quiet Nights Of Quiet Stars,” an outstanding performance of Antônio Carlos Jobim’s poetic love song.

In 1977, Vaughan, then 53, released the first – and best – of three late-career Brazilian-themed albums, the Grammy-nominated I Love Brazil! for producer Norman Granz’s Pablo label. It was recorded in Brazil and featured cameos from a host of local music luminaries, including Antônio Carlos Jobim and Milton Nascimento. Uniformly excellent, the album’s standout track was Vaughan’s sublime cover of Jobim’s “Triste,” featuring graceful woodwind figures and the song’s composer on piano.

Dizzy Gillespie once said “[Sarah Vaughan] can sing notes that other people can’t even hear.” Together with Ella Fitzgerald and Billie Holiday, Vaughan took jazz vocal artistry to new heights. Though she died at age 66 in 1990 from lung cancer, Vaughan lives on through her influence, which has touched many subsequent female jazz vocalists, from Dianne Reeves to Samara Joy. Countless reissues and compilations have helped to preserve her memory; so too have hip-hop artists like Method Man – who sampled her music – and four installments of the Verve Remixed project, in which several of Vaughan’s classic tunes were given a modern makeover by DJs and producers.

Whether presented in an ultra-modern 21st-century electronic context or supported by more traditional jazz musicians and orchestras, Sarah Vaughan’s warm, soulful voice has a unique quality that transcends time. It’s no wonder Tony Bennett once called her “the finest singer in the world.” She was simply divine.

Buy the best Sarah Vaughan songs on vinyl now.