Billy Eckstine

William Clarence “Billy” Eckstine (July 8, 1914 – March 8, 1993) was an American singer of ballads and bandleader of the swing era. Eckstine’s smooth baritone and distinctive vibrato broke down barriers throughout the 1940s, first as leader of the original bop big-band, then as the first romantic black male in popular music.

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Eckstine’s grandparents were William F. Eckstine and Nannie Eckstine, a mixed race, lawfully married couple who lived in Washington D.C.; both were born in the year 1863. William F. was born in Prussia and Nannie in Virginia. His parents were William Eckstein, a chauffeur and Charlotte Eckstein. Billy attended Armstrong High School, St. Paul Normal and Industrial School, and Howard University.[1] He left Howard in 1933, after winning first place in an amateur talent contest.[2] He married his first wife, June, in 1942; she too was a vocalist. After their divorce he married actress and model Carolle Drake in 1953, and remained married until his death. He was the father of 5 children and 2 step children, including Ed Eckstine who was a president of Mercury Records, Guy Eckstine who was a Columbia and Verve Records A&R executive and record producer, and singer Gina Eckstine.[3]

1947 “Everything I have Is Yours”

An influence looming large in the cultural development of soul and R&B singers from Sam Cooke to Prince, Eckstine was able to play it straight on his pop hits “Prisoner of Love“, “My Foolish Heart” and “I Apologize“. Raised in Washington, D.C., Eckstine began singing at the age of seven and entered many amateur talent shows. He had also planned on a football career, but after breaking his collar bone, he made music his focus. After working his way west to Chicago, Eckstine joined Earl Hines‘ Grand Terrace Orchestra in 1939, staying with the band as vocalist and, occasionally, trumpeter, until 1943. By that time, he had begun to make a name for himself through the Hines band’s radio shows with such juke box hits as “Stormy Monday Blues” and his own “Jelly Jelly.”

A Sunday Kind Of Love

In 1944, Eckstine formed his own big band and made it a fountainhead for young musicians who would reshape jazz by the end of the decade, including Dizzy Gillespie, Dexter Gordon, Miles Davis, Art Blakey, Charlie Parker, and Fats Navarro. Tadd Dameron and Gil Fuller were among the band’s arrangers, and Sarah Vaughan gave the vocals a contemporary air. The Billy Eckstine Orchestra was the first bop big-band, and its leader reflected bop innovations by stretching his vocal harmonics into his normal ballads. Despite the group’s modernist slant, Eckstine hit the charts often during the mid-’40s, with Top Ten entries including “A Cottage for Sale” and “Prisoner of Love“. On the group’s frequent European and American tours, Eckstine, popularly known as Mr. B, also played trumpet, valve trombone and guitar.

“A Cottage For Sale”

Dizzy Gillespie, in reflecting on the band in his 1979 autobiography To Be or Not to Bop places it in perspective: “There was no band that sounded like Billy Eckstine’s. Our attack was strong, and we were playing bebop, the modern style. No other band like this one existed in the world.”

After a few years of touring with road-hardened be-boppers, Eckstine became a solo performer in 1947, and seamlessly made the transition to string-filled balladry. He recorded more than a dozen hits during the late ’40s, including “My Foolish Heart” and “I Apologize.” He was one of the first artists to sign with the newly-established MGM Records, and had immediate hits with revivals of “Everything I Have Is Yours” (1947), Richard Rodgers’ and Lorenz Hart’s “Blue Moon” (1948), and Juan Tizol’s “Caravan” (1949).


Eckstine had further success in 1950 with Victor Young’s theme song to “My Foolish Heart” and a revival of the 1931 Bing Crosby hit, “I Apologize“. However, unlike Nat “King” Cole (who followed him into the pop charts), Eckstine’s singing, especially his exaggerated vibrato, sounded increasingly mannered and he was unable to sustain his recording success throughout the decade.

“Body and Soul”

While enjoying success in the middle-of-the-road and pop fields, Eckstine occasionally returned to his jazz roots, recording with Vaughan, Count Basie and Quincy Jones for separate LPs, and he regularly topped the Metronome and Downbeat polls in the Top Male Vocalist category: He won Esquire magazine’s New Star Award in 1946; the Down Beat magazine Readers Polls from 1948 to 1952; and the Metronome magazine award as “Top Male Vocalist” from 1949 to 1954.

His 1950 appearance at the Paramount Theatre in New York City drew a larger audience than Frank Sinatra at his legendary Paramount performance.

Among Eckstine’s best records of the 1950s was a 1957 duet with Sarah Vaughan, “Passing Strangers“, a minor hit in 1957, but a perennial hit in the UK. Even before folding his band, Eckstine had recorded solo to support it, scoring two million-sellers in 1945 with “Cottage for Sale” and a revival of “Prisoner of Love“. Far more successful than his band recordings, though more mannered and pompously sung, these prefigured Eckstine’s future career. Where before black bands had played ballads, jazz and dance music, in the immediate post-war years they had to choose.

“My Foolish Heart”

The classic 1960 live in Las Vegas LP No Cover, No Minimum featured Eckstine taking a few trumpet solos as well. He recorded several albums for Mercury and Roulette during the early 1960s, and he appeared on Motown for a few standards albums during the mid-’60s. After recording very sparingly during the ’70s for Al Bell’s, Stax/Enterprise imprint, Eckstine (although still performing to adoring audiences throughout the world), made his last recording, the Grammy-nominated Billy Eckstine Sings with Benny Carter in 1986.

Eckstine made numerous appearances on television variety shows, including “The Ed Sullivan Show”, “The Nat King Cole Show”, “The Tonight Show” with Steve Allen, Jack Paar, and Johnny Carson, “The Merv Griffin Show“, “The Art Linkletter Show,” “The Joey Bishop Show,” “The Dean Martin Show“, “The Flip Wilson Show“, and “Playboy After Dark“. He also performed as an actor in the TV sitcom “Sanford and Son“, and in such films as Skirts Ahoy, Let’s Do It Again, and Jo Jo Dancer.

Eckstine was a style leader and noted sharp dresser. He designed and patented a high roll collar that formed a “B” over a Windsor-knotted tie, which became known as a “Mr. B. Collar.” In addition to looking cool, the collar could expand and contract without popping open, which allowed his neck to swell while playing his horns. The collars were worn by many a hipster in the late 1940s and early 1950s. Legend has it that his refined appearance even had an effect on trumpeter Miles Davis. Once, when Eckstine came across a disheveled Davis in the depths of his heroin excess, his remark “Looking sharp, Miles” served as a wake-up call for Davis, who promptly returned to his father’s farm in the winter of 1953 and finally kicked the habit.[4]

With Nat King Cole, “Rosetta”

In 1986, Billy recorded his final album Billy Eckstine Sings with Benny Carter. Eckstine died on March 8, 1993, aged 78.

Quincy Jones quoted in Billboard: “I looked up to Mr. B as an idol. I wanted to dress like him, talk like him, pattern my whole life as a musician and as a complete person in the image of dignity that he projected… As a black man, Eckstine was not immune to the prejudice that characterized the 1950s”. Quincy Jones is quoted in The Pleasures of Jazz as saying of Eckstine: “If he’d been white, the sky would have been the limit. As it was, he didn’t have his own radio or TV show, much less a movie career. He had to fight the system, so things never quite fell into place.””

“When Somthing’s Wrong”

Finally, Lionel Hampton, legendary vibraphonist: “He was one of the greatest singers of all time. We were proud of him because he was the first Black popular singer singing popular songs in our race. We, the whole music profession, were so happy to see him achieve what he was doing. He was one of the greatest singers of that era. He was out singer.”

Sources: wikipedia, youtube,,


  • 1961 Broadway, Bongos and Mr. B (Mercury)
  • 1962 Don’t Worry ’bout Me (Mercury)
  • 1964 12 Great Movies (Mercury)
  • 1964 Modern Sound of Mr. B (Mercury)
  • 1965 Prime of My Life (Motown)
  • 1966 My Way (Motown)
  • 1969 For Love of Ivy (Motown)
  • 1971 Feel the Warm (Enterprise)
  • 1971 Moment (Capitol)
  • 1972 Senior Soul (Enterprise)
  • 1974 If She Walked into My Life (Enterprise)
  • 1978 Memento Brasiliero – (Portuguese)
  • 1984 I am a Singer
  • 1986 Billy Eckstine Sings with Benny Carter (Verve)
  • 1994 Everything I Have Is Yours – Anthology (Verve)
  • 1995 I Apologize (Polydor)
  • 2002 How High the Moon (Past Perfect)
  • 2002 Billy Eckstine and His Orchestra (Deluxe)
  • 2002 Stardust (Polydor)
  • 2003 The Motown Years (Motown)
  • 2004 Love Songs (Savoy)
  • 2006 Timeless (Savoy)

1 Comment

  1. Wow! Loved the ‘Rosetta’ clip. What a great ‘2-fer’–Ekstine and Cole. And…it’s lovely to be able to hear Mr. B sing ‘Everything I Have Is Yours’ whenever I feel like. Thanx!

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