Billy Eckstine; Singer of Hit Tunes Also Was a Pioneer of Be-Bop Style

Billy Eckstine, the handsome, dapper, bandleader and vocalist who turned out popular hits in the 1940s and ‘50s while playing a pivotal role in the formative years of be-bop, died Monday in Pittsburgh.

A spokeswoman for Mercury Records in New York said he died at Montefiore Hospital of complications of a stroke that he suffered last year.

He lived in Las Vegas but had gone to Pittsburgh for treatment.

The bass-baritone with the resonant voice was 78.

Eckstine’s musical odyssey took many turns in its six decades--from bandleader to balladeer, from near-superstardom to near-bankruptcy. But he never lacked for fans, whether they were admirers of such love songs as “Fools Rush In” or musicologists intrigued with such Eckstine sidemen as Dizzy Gillespie, Charlie Parker and Dexter Gordon.

His hit records between 1945 and 1951 included “A Cottage for Sale,” “Prisoner of Love,” “I Surrender, Dear,” “Everything I Have Is Yours,” “Blue Moon,” “My Foolish Heart,” “Caravan,” “Body and Soul” and “I Apologize.” His last big hit was “Passing Strangers,” a duet with the late Sarah Vaughan, whom he helped discover.

And when he was not singing, he was swinging on valve trombone or trumpet.

Born William Clarence Eckstein in Pittsburgh, the singer and instrumentalist was asked to change his name by a nightclub owner who thought it looked “too Jewish.”

The youngest of three children, Eckstine grew up in Pittsburgh and in Washington, D.C.

The man dubbed “the Sepia Sinatra” recalled in a long-ago Negro Digest interview that his father, a chauffeur, bought a piano for the family when one of the girls showed promise as a musician. It was her brother, however, who began to show the greater talent.

He apparently came naturally to the singing voice that Duke Ellington dubbed “sensuous semantics.”

Eckstine enrolled in college--first at St. Paul Normal and Industrial School in Lawrenceville, Va., then at Howard University in Washington--but after a year he won an amateur music contest at the nearby Howard Theater. The prize, a week as a singer with the theater band, for $10 a show, proved the springboard for Eckstine’s career.

Inspired by this beginning, “Mr. B” as he came to be known, launched his career in 1934 in a Buffalo, N.Y., nightclub as a singer and emcee.

Five years later, Eckstine went to Chicago as principal vocalist for the Earl (Fatha) Hines big band. With them he wrote and recorded “Jelly Jelly,” his first million-selling hit. Such other successes as the blues-oriented ballads “Somehow,” “You Don’t Know What Love Is” and “Skylark” quickly followed.

Eckstine also had a keen eye for talent. That became evident when he coaxed Hines into hiring Vaughan, whom he had first seen in an amateur show.

During the early 1940s, jazz clubs dotted most big cities and there was steady work for those with stamina and desire, Eckstine recalled in a 1983 interview. The worst part was touring the South, where food and lodging for “coloreds” were about as hard to come by as a seat at the front of a bus, he said.

Eckstine decided in the spring of 1944 to form his own band, filling it with musicians who would incubate the bop movement: Gillespie, Fats Navarro, Miles Davis, Parker, Gordon, Kenny Dorham, Art Blakey, Gene Ammons and others. Eckstine became so caught up in the music that he took up brass, playing the valve trombone and trumpet between vocals.

However, many saw the band as inconsistent, for Eckstine was courting young avant-garde jazz musicians while crooning conservative popular ballads.

Be-bop, rooted in New Orleans jazz and swing, represented a radical increase in complexity because many bop themes were based largely on ninth, 11th, and 13th chords, unlike those of previous jazz styles.

Despite being light-years ahead of its time, or maybe because of it, Eckstine’s orchestra failed to generate wide acceptance and disbanded after three years. “It got to the point where making ends meet was getting harder and harder,” Eckstine said in a Times interview. So from 1948 on Eckstine stayed with commercial balladry. With his sweet tones, good looks and impeccable delivery, he rivaled such white superstars as Frank Sinatra and Bing Crosby.

Throughout the 1950s, Eckstine, accompanied by his omnipresent pianist, Bobby Tucker, endured as one of the nation’s top male vocalists, winning polls and earning gold records for his recordings of such standards as “Fools Rush In” and “A Cottage for Sale.”

By that time his music had found a mainstream audience and he began appearing in white-owned magazines and newspapers. Although he was becoming a national sex symbol, superstardom eluded him. Crosby and Sinatra were film stars but Hollywood balked at a black leading man.

But his appeal crossed over to white audiences, and not just musically. The oversized Eckstine roll collar, loosened tie and casually draped jacket came to represent a rite of passage among big-city American youths.

Ellington recalled in the anthology “The Best of the Music Makers” that when he and Eckstine once worked the same theater, “neither of us wore the same suit twice. . . . By the third week, people were buying tickets just to see the sartorial changes.”

In 1953 the svelte, six-foot Eckstine married Carrolle Drake, his second wife. A 1942 marriage had ended in divorce. He and Miss Drake had seven children before their divorce in 1977.

One of his children, Gina, performed regularly on the Las Vegas circuit with her father in his later years. A son, Ed, is president of Mercury Records.

In 1986, claiming Eckstine owed $251,000 in back taxes, the Internal Revenue Service raided his country club townhouse in Las Vegas and confiscated 110 items of personal property, including three gold records and dozens of musical instruments.

Subsequently, published reports said, an unidentified entertainer and longtime friend purchased the gold records and personal memorabilia from the IRS, saving them from public auction.

Although Eckstine worked in semi-obscurity throughout most of the 1970s, ‘80s and ‘90s, he never lacked work. He performed regularly in Miami, California and Las Vegas. “There are about eight or nine things people ask for,” he told The Times in a 1986 interview. Among them (all gold records): “Fools Rush In,” “Everything I Have Is Yours,” “Caravan,” ’Prisoner of Love” and “A Cottage for Sale.”

To stay contemporary, he had also begun playing guitar.

But Eckstine explained that his personal favorite was “a song that wasn’t a favorite to anybody else,” called “Weaver of Dreams,” written by Victor Young.

“I recorded it, and Nelson Riddle did the backup,” Eckstine said. “(But) hell, my mother didn’t even buy it.”

As for retiring, he said: “I think the public will let you know. . . . If you look out there and don’t see anyone you’re in trouble.”