Records from ancestry.com indicate that the singer has an interesting geneology. His grandparents were William F. Eckstein and Nannie Eckstein, 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.
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."
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.
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). He 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. 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. His 1950 appearance at the Paramount in New York drew a larger audience than Frank Sinatra had 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.
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 dishevelled 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.
In 1984, Eckstine recorded his final album, I Am A Singer, featuring beautiful ballads arranged and conducted by Angelo DiPippo.
Billy Eckstine died on March 8, 1993, aged 78.