Billy Eckstine

By the time he reached his peak popularity in 1950, he rivaled Frank Sinatra as the country's most popular vocalist. In fact he was dubbed "the sepia Sinatra," although he was known most often as "Mr. B." Billy Eckstine was a smooth singer also noted as a premier jazz bandleader in the 1940s, gathering many of the performers in the innovative bebop style into a unique large band.

Born William Clarence Eckstein in Pittsburgh, Pennsylvania, in 1914, Eckstine had the spelling of his name changed early in his career by a club owner. The family moved to Washington, D.C. Eckstine's parents stressed education, and he graduated from Washington's Armstrong High School. He began to sing when he was 11, but was a football player in high school and aspired to a sports career for a time. Eckstine went on to college at the city's Howard University. A first-place finish in a talent contest at a Washington theater put an end to his educational career, however; he dropped out of school to sing full time.

At first Eckstine appeared in and around Washington, D.C., but had moved to Chicago by 1937. Pianist and bandleader Earl Hines hired him as his lead vocalist for his Grand terrace Orchestra in 1939. During a four-year stint with Hines, Eckstine broadened his vocal skills, learned to play the trumpet, and met many of the jazz players who were experimenting with new styles. All this made for ideal training as Eckstine dreamed of starting a band of his own. He notched several hits with Hines, the first of which was the bluesy "Jelly, Jelly" of 1940. When he introduced the song "Skylark" on a network radio program, he was the first African American vocalist to premiere a mainstream pop song on the radio.

In 1943 Eckstine was ready to launch his own group, the Billy Eckstine Band. He put together a group of the most talented young players he encountered, and the roster would read like an account of the performers who would dominate jazz over the next two decades. Among those who passed through Eckstine's band were Charlie Parker, Miles Davis, Sarah Vaughan, Dizzy Gillespie, Fats Navarro, Gene Ammons, Dexter Gordon, and Art Blakey.

Eckstine's initial intention was simply to gather a backing group for his own vocal numbers, but he had the experience and insight to realize the unique opportunities his ensemble offered. Many of them had participated in the formation of the radical new style that became known as bebop. Eckstine was able to adapt this sound to a big-band format and is generally credited with forming the first bebop big band.

In the hands of Gillespie and other followers, big-band bebop would become a durable jazz style. At the time, however, Eckstine's experiments enjoyed only limited commercial success. He had more luck with the romantic ballad style he had been cultivating under Hines; a harbinger of his crossover success came when the band toured the South in 1944 and several promoters dropped the prevalent requirement that the audience be segregated by race. That tour grossed over $100,000 in ten weeks, a figure that made music-industry figures sit up and take notice.

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. Lacking an interest in the blues and frustrated by the failure of his big band, Eckstine, at first reluctantly, turned to ballads. Henceforth his successes would be in the pop charts.

In 1947, he was one of the first signings to the newly established MGM Records and had immediate hits with revivals of “Everything I Have Is Yours,” (1947), Rodgers’ and Hart’s “Blue Moon,” (1948), and “Caravan.” (1949) He toured with the Count Basie Orchestra and the middle-of-the-road George Shearing Quintet. He had further success in 1950 with Victor Young’s theme song to ‘My Foolish Heart’ and a revival of the Bing Crosby hit, ‘I Apologize’. ). By 1950 he was MGM's top-selling artist and was selling out major venues like New York's Paramount Theater. 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. His best record of the fifties was the thrilling duet with Sarah Vaughan, “Passing Strangers,” a minor hit in 1957.

Eckstine's appeal began with his baritone vocals, so well crafted that he considered a move into classical music for a time. But equally central to his success was his image. Eckstine's narrow ties and loose-fitting, relaxed jackets became fashion trendsetters, and the singer became a romantic icon whose audiences over time grew to include a substantial proportion of white listeners.

The decline of bebop, swing and the rise of the blues and country styles that produced rock and roll finally diminished Eckstine's popularity somewhat, although he continued to be much sought-after as a top nightclub attraction through the 1950s and 1960s. Eckstine returned to his jazz roots occasionally as well, recording with Vaughan, Count Basie, and Quincy Jones for separate sessions, and the 1960 live date “No Cover, No Minimum,” featured him taking a few trumpet solos as well. He recorded several albums for Mercury and Roulette during the early '60s, and he appeared on Motown for a few standards albums during the mid-'60s. After recording very sparingly during the '70s, Eckstine made his last recording “Billy Eckstine Sings with Benny Carter,” in 1986. He died of a heart attack in 1993.

Billy Eckstine was top male vocalist, Metronome magazine, 1949 and 1950; voted most popular singer, Down Beat readers' poll, 1949 and 1950. He left an impressive legacy of recordings in a distinguished trajectory through music of over fifty years. Show less