Since its beginnings at the dawn of the 20th century, jazz music has always been a happy hunting ground for singers with expressive power.
Whether it's the searing emotional honesty of Nina Simone or the irrepressible joy of Louis Armstrong in his prime, jazz has proved a brilliant backdrop for those singers who want to deliver a little extra emotion. Here are some of the best jazz singers: the most arresting performers ever to stride up to a jazz-club microphone.
Best jazz singers of all time: the top 15
15. Blossom Dearie (1924-2009)
A charming, understated singer with a distinctive, light voice and a sophisticated sense of phrasing, known for her witty, intimate performances.
When Blossom Dearie died, the obituaries began by declaring that that really was her given name. It seemed too good to be true, the winsome image so perfectly suited the doll-like delivery which had made her a unique presence on the international scene for over half a century.
Dearie’s personal territory was the jazz-cabaret frontier, an adroit blend of delicate swing and wit. As her fellow musicians well knew, she was a collector and connoisseur of good tunes, savouring clever lyrics and chord changes, which she projected with subtlety, insight and humour.
Essential listening: 'I Wish You Love'
14. Jimmy Rushing (1901-72)
A powerful blues shouter, best known for his work with the Count Basie Orchestra. His voice was a major force in swing-era jazz.
Not many vocalists inspire their own signature tune, but Jimmy Rushing was the unmistakable model for ‘Mr Five by Five’. A tribute to his roly-poly frame, the phrase was his nickname throughout his 50-year career and reflected his perennially good-humoured style.
He wasn’t built for tragedy, and his strength as a singer was an infectious, gravelly assurance. Despite being identified with the blues, he sang all kinds of songs, starting off in his hometown of Oklahoma City, touring as an itinerant entertainer and winding up in the precincts of Kansas City, where he joined the Count Basie band in 1935.
We just love the way he imperiously shoulder-barges the great Dizzy Gillespie aside in this clip.
Essential listening: 'Boogie Woogie (I May Be Wrong)'
13. Mose Allison (1927-2016)
A jazz pianist and singer with a unique, cool, blues-inflected vocal style, known for his witty, laid-back delivery.
Octogenarian Mose Allison, in a career stretching back beyond five decades, has produced a unique body of work. Allison’s songs are unmistakeable – wry, bluesy comments on the contemporary scene that manage to be streetwise and satiric, down-home and hip. While they might not have made him a household name, they have earned him the devotion of fans all over the world, and the respect and emulation of a couple of generations of his fellow singers, including stars of rock and pop.
Essential listening: 'Parchman Farm'
We also named Mose Allison one of the best jazz pianists ever
12. Leadbelly
More of a folk-blues artist, but his powerful voice and storytelling ability had a significant impact on early jazz and popular music.
Ordinary Huddie Ledbetter, known as ‘Leadbelly’, certainly wasn’t. Born in rural Texas in c.1888, regal in bearing and strong as an ox, he claimed to be the world’s greatest cotton picker, railroad track layer, lover, drinker and guitar player.
His pride was matched by a temper and disposition to violence, resulting in spells in prison for assault and murder. And it was in 1933, in the Louisiana State Penitentiary, that he was discovered by folk song collectors John and Alan Lomax.
Under the sponsorship of the Lomaxes, Leadbelly began his rise to stardom, benefiting from the gathering vogue for trad jazz and rugged authenticity. He gave concerts across the US and Europe, dying in New York in 1949.
Essential listening: 'Goodnight, Irene'
Leadbelly was also one of the four greatest jazz guitarists of all time
11. Cab Calloway
A charismatic performer and bandleader who brought jazz singing to the mainstream with his flamboyant, high-energy delivery and call-and-response style.
Singer, dancer, jive talker and dresser, Cab Calloway was a true jazz master of the revels. His exuberant personality overshadowed his reputation as one of the greatest jazz band leaders.
Through the 1930s and ’40s, Calloway’s orchestra accompanied his outrageous vocal displays and boasted an array of talent: tenorist Chu Berry, drummer Cozy Cole, bassist Milt Hinton and trumpeters Jonah Jones and bebop enfant terrible Dizzy Gillespie.
Essential listening: 'Minnie the Moocher'
Best jazz singers: the top ten
10. Kurt Elling
One of modern jazz’s great male vocalists, known for his daring improvisations, deep baritone, and ability to bring literary sophistication into jazz singing.
Listening to Kurt Elling brings to mind the essential jazz paradox – that it’s an art music whose purpose has been to sell booze. This is especially true of jazz singing, that vague crossover area in which hip performers croon standards with a bit of beat, indulge a taste for sassy subversion or toss off ‘shooby-dooing’ scat.
Though that kind of amiable entertainment may keep the customers happy, it’s not how Kurt Elling sees jazz. Intense, passionate, fearlessly ambitious, his vocal style ranges the gamut of his imagination, from searing ballads and improvisations to his own vocalese settings of classic instrumental solos, such as John Coltrane’s epic ‘Resolution’.
Essential listening: 'Nature Boy'
9. Bobby McFerrin
A vocal magician with an astonishing range and ability to use his voice like an instrument, known for his groundbreaking a cappella and jazz fusion work.
It was Emma Kirkby who first introduced me to Bobby McFerrin: she declared in a radio interview that he had ‘the most amazing voice I’ve ever heard’, and as evidence played ‘I’m My Own Walkman’. My McFerrin epiphany followed not long after in a live 90-minute solo concert where his only props were a cordless mic and a bottle of water.
‘Amazing’ barely described it: a four-octave range from basso profondo to falsetto; seemingly limitless inspiration, energy and wit; a throbbing beat that came from the singer’s thumped chest and rhythmic gasps; dazzling improvisations in which his bebop flights were accompanied by audience riffs he dictated on the spot.
Essential listening: 'Don’t Worry, Be Happy'
8. Betty Carter
A master of complex phrasing and harmonic adventurousness, Carter was one of the most innovative vocalists in jazz history.
The title that Betty Carter gave one of her last CDs epitomised her approach to jazz singing: It’s Not About the Melody. For over half a century she transformed standard popular songs into vehicles for her unique personal expression.
A live Carter performance encompassed joyous innocence, shattering insight and musical virtuosity, both from the singer and the young accompanists. In a Verve Finest Hour compilation she inspires her rhythm section with energy and invention just as if she were a horn, a living reproach to those diehards who secretly feel that the phrase ‘jazz singer’ is a contradiction. But Betty Carter was a musician who happened to sing, a jazz voice whose achievements continue to astound.
Essential listening: 'Open the Door'
7. Bessie Smith
The “Empress of the Blues” laid the foundation for jazz and blues vocals, influencing nearly every jazz singer who followed.
Historically, you can’t have jazz without the blues. To savour the essence of the blues, any listener should experience the majesty of Bessie Smith. Her first recording, in 1923, established her as a unique vocalist, with a huge sound and mesmerising presence. She maintained her eminence throughout the ’20s, her repertoire encompassing pop songs and novelties as well as her staple blues.
Her genius for expression was forged in a lifetime of stage performance. A Smith show could seem quasi-religious, with the crowd moaning and crying ‘Amen’. But her appeal was sexual, too: a favourite trick was to ‘walk one’, singing directly at a male member of the audience until he stumbled trance-like toward the stage.
Essential listening: 'Nobody Knows You When You’re Down and Out'
6. Nina Simone
A genre-defying artist who infused jazz with blues, classical, and protest music, making her one of the most compelling and original voices in history.
A veritable African-American icon and a singer much loved by fans of jazz, blues, soul, gospel and more, Nina Simone had great charisma and a truly distinctive voice. A superbly gifted singer, pianist, and songwriter, Simone could turn her hand to compositions in many genres.
Whatever she tackled, she did so with passion and a searing emotional honesty. A whole host of musicians from right across the musical spectrum, from David Bowie and Elton John to Janis Joplin and Van Morrison, have cited Simone as a major influence on their musical development.
As we've discussed in another article, Nina Simone faced racial prejudice early in her performing career: she had her heart set on becoming a classical pianist, having learned the music of Bach, Beethoven, Brahms, Chopin and Schubert as a young girl.
On leaving school, Nina Simone was awarded a year’s scholarship to the Juilliard School of Music in New York. The plan was that she should then apply for a full scholarship to the Curtis Institute of Music in Philadelphia, prompting her family to relocate there. When the expected scholarship failed to materialise she was dismayed. However, and however unfair the decision may have been, classical music's loss was undoubtedly jazz's gain.
Essential listening: 'Feeling Good'
Best jazz singers: the top five
5. Frank Sinatra
Though more of a pop crooner than a jazz singer, his impeccable phrasing and swing feel made him a major influence in jazz vocal interpretation.
When you're making a list of the most important musical figures of the 20th century, Frank Sinatra has to take his place at the top table alongside the likes of The Beatles and Elvis Presley. A singing career that lasted the best part of six decades saw Sinatra win and maintain an impressive popularity - always seeming relevant through the eras of swing (1030s-40s), the big singers of the 1940s and 1950s, and into and beyond the birth of rock and roll.
Sinatra really made his name with his rich, warm and soulful recordings of numbers by the great early 20th century American musical theatre composers, such as George Gershwin, Cole Porter, Richard Rodgers, Jerome Kern, and Irving Berlin. Sinatra's gift was to inject these standards with charm, soul, musicality and (when required) humour, helping to set them down as classics.
Essential listening: 'My Way'
4. Sarah Vaughan
Known for her rich, operatic tone and incredible range, she combined technical brilliance with deep emotional expression.
A true jazz diva, Sarah Vaughan bewitched listeners with her sheer beauty of sound and supple invention. Her blend of sensual sonority and technical command earned her the public sobriquet of ‘The Divine One’; her fellow musicians, impressed by her confidence, dubbed her ‘Sassy’.
A capable pianist as well as a singer, she came of age with the bebop pioneers, recording with Dizzy Gillespie and Charlie Parker, who admired her deeply. But from the ’50s, her sumptuous voice, with its four-octave range and operatic agility, attracted the attention of the pop industry. For much of her career, she veered between the two worlds, winning a middle-of-the-road following for albums of dreamy ballads with strings, while charming jazz fans with her swing and artful phrasing.
3. Louis Armstrong
While primarily known as a trumpeter, his gravelly voice and charismatic delivery revolutionized jazz singing. A founding father of jazz itself.
Armstrong’s unique scat vocals brought a new dimension to improvisation: a piece like ‘Heebie Jeebies’ seems an outpouring of pure joy, a song that doesn’t need words to convey its rhythmic and melodic gusto. And on the magnificent ‘West End Blues’, his trumpet and vocal powers combine to produce a masterpiece of searing emotion.
Essential listening: 'What a Wonderful World'
2. Billie Holiday
The most emotionally expressive jazz vocalist, influencing countless singers with her phrasing and unique ability to convey deep emotion.
Billie Holiday was an improviser of genius. Her ability to give an ordinary pop tune a subtle new shape and depth of meaning made her that most elusive of beings, a true jazz singer.
She remains, very likely, the best. Her youthful records from the ’30s still constitute a benchmark for jazz vocalists. In them, Lady Day is the peer of the all-star casts who surround her – chief among them her soulmate, tenorman Lester Young.
Together, she and Young spin wonders like their impromptu duet on ‘Me, Myself and I’, which Holiday launches with a deft quotation from her main influence, Louis Armstrong. But her phrasing, swing and confidence are her own, as in her assured entrance on ‘Miss Brown to You’, sliding across the beat, yet clear as a bell.
Essential listening: 'Strange Fruit'
Best jazz singers: and the greatest of them all is...
1. Ella Fitzgerald
The greatest jazz singer in terms of technical mastery, improvisational skill, and sheer longevity. Her scat singing and perfect intonation set the gold standard.
Besides her infectious way with pop songs, Ella Fitzgerald revealed the kind of full-throttle skill at improvisation which was usually the domain of instrumentalists.
Her power as a scat singer bursts out from her 1945 recording of ‘Flying Home’, and ‘Smooth Sailing’ from 1951 shows her at home in rhythm and blues. Records like these make you understand why she was the brightest star of Norman Granz’s Jazz at the Philharmonic tours, and the one who would close the show.
Jazz lovers loved the spectacle of Ella live, backed just with a rhythm section, storming through such impromptu masterpieces as ‘Mack the Knife’ and ‘How High the Moon’, recorded at a 1960 concert in Berlin. We’re left gasping at her energy, invention and exhilarating creativity; her songs enshrine a life committed to performing and a conviction that joy is the essence of jazz.
Essential listening: 'Summertime'