Eckstine, William Clarence (“Billy”)

(b. 8 July 1914 in Pittsburgh, Pennsylvania; d. 8 March 1993 in Pittsburgh, Pennsylvania), popular baritone singer whose smooth delivery on love ballads made him a sex symbol in the African American community; he led an influential jazz band in the mid-1940s that served as an important breeding ground for musicians of the emerging bebop style.

Eckstine was born William Clarence Eckstein, the youngest of three children of Clarence William and Charlotte Eckstein. His father held various jobs including chauffeur; his mother was a homemaker. He began singing at age seven, probably in the family’s Episcopal church in the East Liberty neighborhood of Pittsburgh.

Although he pursued singing throughout his early life, Eckstine at this stage was more interested in sports than in music. On his own, he went to Armstrong High School in Washington, D.C., and St. Paul Normal and Industrial School in Lawrenceville, Virginia, to play high school football, earning an athletic scholarship to Howard University in 1932. Enrolled as a physical education major, he was injured and withdrew less than a year later.

While in Washington, Eckstine gained a reputation as a singer of ballads and blues through his work with Tommy Myle’s band. Imitating the entertainer and orchestra leader Cab Calloway, he won an amateur contest at the Howard Theater in 1933. Returning to Pittsburgh in 1934, Eckstine encountered the tenor saxophonist Budd Johnson—a childhood acquaintance and member of the pianist Earl Hines’s orchestra—who advised him to move to Chicago. Eckstine left Pittsburgh in 1936, lived in Buffalo, New York, for most of 1937, and then lived in Detroit before arriving in Chicago in early 1938.

He entertained at Ralph Capone’s Club De Lisa until 1939, when Hines heard him and offered him a job with his orchestra, then nearing the end of its long and storied residence at the Grand Terrace Hotel. Together with Johnson, Eckstine helped to revive Hines’s sagging fortunes by attracting the best and most innovative young musicians to play in his band.

In 1940 a blues song, “Jelly, Jelly,” hastily conceived by Eckstine and Johnson to use up excess studio time, became the singer’s first hit with Hines. A classic ballad performance, “Skylark,” followed in 1942, and Eckstine’s career was launched. In late 1942, “Stormy Monday Blues” by Hines, featuring Eckstine, was the number one rhythm-and-blues (or as it was known then, “race music”) song in the country, staying on the chart for fourteen weeks.

Among the young modernists who Eckstine helped attract to the Hines band were the trumpeters “Dizzy” Gillespie and “Little Benny” Harris, the alto saxophonist Charlie Parker (who played tenor while with Hines), the tenor saxophonists Gene Ammons and Wardell Gray, and the vocalist Sarah Vaughan. Unfortunately this seminal band made few recordings. Because of a ban on recordings by the American Federation of Musicians—which in 1942 demanded better contract terms with the recording industry—as well as wartime shortages of the materials used to make recording discs, only a few documents of this brief era of jazz survive.

Eckstine, who did not serve in World War II because of a sports injury, left Hines in September 1943 to embark on a solo career in New York City. Following a brief period in which he was billed on Fifty-second Street as “Billy X-Tine,” he decided to form a big band of his own. Although the Billy Eckstine Orchestra, launched in June 1944, was an economic failure, it was an important harbinger of things to come in jazz. The band toured the southern United States and had a few hit records for the De Luxe and National labels—mostly ballads, including such staples of Eckstine’s later repertoire as “A Cottage for Sale” (1945) and the old Russ Columbo warhorses “Prisoner of Love” and “You Call It Madness” (1946). In 1944 he recorded a Tadd Dameron arrangement of his own composition, “I Want to Talk About You,” a sublime statement of love subsequently recorded by the tenor saxophonist John Coltrane and others. Sometime around 1944, Eckstine changed his surname’s spelling to “Eckstine.”

Eckstine sidemen, the trumpeter Miles Davis and the drummer Art Blakey, went on to become famous bandleaders themselves. The band also boasted, at various times, the trumpeters Gillespie, Fats Navarro, and Kenny Dorham, and the saxophonists Dexter Gordon, Lucky Thompson, Gene Ammons, Parker, and Sonny Stitt. Some critics and listeners recognized the progressiveness of the music, while others found the juxtaposition of smooth vocal ballads and avant-garde bop instrumentals unsettling. In later interviews Eckstine scoffed at the critics who had faulted his band’s sound in the early days, only to reverse their opinion once the group’s significance to jazz history was known.

Eckstine had blue eyes and pretty-boy looks, and as a young man he would not hesitate to fight if provoked. In the film short Rhythm in a Riff (1946), he is shown singing and conducting the big band, and he solos competently on valve trombone. He began playing trumpet while with Hines, partly as a way of teaching himself to read music, but switched to valve trombone in his own band, he said, to counterbalance the trumpet and saxophone soloists. When he gave up the big band along with the trombone in 1947, he continued to play trumpet in his nightclub act. Dizzy Gillespie absorbed the remnants of the Eckstine band into his own group and added some irreverent clowning, finally achieving wide success with big band bop in 1949.

Turning to Hollywood, Eckstine found doors partly closed because of racial prejudice. Signing with Metro-Goldwyn-Mayer’s nascent MGM Records, he had a string of hits working with various arrangers including Russ Case and Pete Rugolo, and rose quickly to become the most popular American male vocalist of 1949–1950. Like Nat King Cole, he presented an image of the contemporary African American male that was strong, sophisticated, romantic, sensitive, and intelligent. His appeal transcended boundaries of race, and he set box office records in New York while being mobbed by the “Billy soxers” who came to hear him sing love songs like “Everything I Have Is Yours” (1947), “Somehow” (1948), “My Foolish Heart” (1949), and his theme, “I Apologize” (1950).

He toured lucratively with the pianist George Shearing in 1950 and 1951, and ignited a fashion craze in the United States and England with his trademark “Mr. B.” cotton shirts, which had a rolled, floppy collar. An avid golfer, he was the subject of feature articles in Life (1950) and Look (1951) magazines. Yet MGM mostly denied Eckstine the opportunity to expand his talent into movies—with the exception of a cameo appearance in the 1952 Esther Williams vehicle, Skirts Ahoy! Years later his friend the producer Quincy Jones commented, “They never let him become the sex symbol he could have been. If he’d been white, the sky would have been the limit. As it was he didn’t even 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.”

Eckstine’s popularity waned with the arrival of rock music in the early 1950s. He turned again to the jazz scene, helping Count Basie to reestablish his orchestra after its collapse in 1951. He and his wife, June, divorced in 1953 (they had married in 1942, and had no children). Later that year he married Carolle Drake. They had seven children before the marriage ended in divorce in 1977. Eckstine also had an eighth child by another woman during his second marriage. Eckstine made the charts one last time for MGM with “Passing Strangers,” a duet with Sarah Vaughan, in 1957. By then he had settled into a comfortable career as a nightclub singer, a position that he was able to maintain for the rest of his life in Las Vegas and Reno, Nevada, and Atlantic City, New Jersey.

After briefly signing with RCA, Eckstine signed with Morris Levy’s Roulette label in 1960, recording both Basie-Eckstine, Inc. with Count Basie, and No Cover, No Minimum with his regular accompanist since 1949, Bobby Tucker. In 1961 he signed a five-album deal with Mercury Records and recorded Live at Basin Street East with Quincy Jones’s orchestra.

He toured Europe and Asia and maintained homes in Las Vegas and Encino, California, as well as an apartment on 125th Street in the Harlem neighborhood of New York City. Typically he would work thirteen-week engagements at the Las Vegas casinos. The performances and subsequent partying would be followed by a round of golf in the morning, with Eckstine getting to bed in the early afternoon, waking up in time for the evening’s performance.

Eckstine signed with Motown Records in 1965, but the resultant two albums did not sell well. The same was true of three albums he made for Stax in the late 1960s and early 1970s. In 1966 he performed with Duke Ellington. By the 1970s he had matured into a beloved celebrity, making guest appearances in television and films—a debonair, living symbol of a more romantic time in history.

In 1979 Eckstine toured with his daughter Gina, a singer. He recorded with saxophonist Benny Carter in 1986 for Mercury, where his son Ed was an executive. That year, he made his final album, I Am a Singer, for Kimbo Records. He continued to tour and carry out his nightclub engagements until his death from a stroke. He was cremated and his ashes were distributed among the surviving family members.

Eckstine’s name is synonymous with the smooth style of baritone ballad singing that he perfected. Subsequent singers who have shown the Eckstine influence include Joe Williams, Arthur Prysock, Luther Vandross, Kevin Mahogany, and Brian McKnight. While essentially a popular singer, he maintained strong ties to jazz throughout his career, and was highly regarded in both the world of entertainment and the African American community.

Eckstine wrote a three-part series about leading his band for the British music magazine Melody Mailer in 1954; he also granted interviews to Metronome (Feb. 1949, July 1950, and Jan. 1951), Soul (14 Oct. 1974), and Jazz Times (June 1984). Information about Eckstine’s bop band may be found in Ira Gitler, Jazz Masters of the ‘40s (1966), Ira Gitler, Swing to Bop: An Oral History of the Transition in Jazz in the 1940s (1985), as well as in Scott DeVeaux, Birth of Bebop: A Social and Musical History (1997). Further information about the bop era may be found in Dizzy Gillespie, To Be, or Not. . . to Bop, Memoirs (1979; rev. ed. 1999). Information about the Earl Hines Orchestra is found in Stanley Dance, The World of Earl Hines (1977). An obituary is in the New York Times (9 Mar. 1993).

Gregory K. Robinson