Billy Eckstine

Mr. B -Influential Band Leader and Top Male Vocalist

Billy Eckstine was the leader of the first bop big-band and then became the first romantic African American male vocalist in popular music. Noted for his smooth deep baritone and distinctive vibrato he sang the classic pop hits "Prisoner of Love," "My Foolish Heart" and "I Apologize."  Having 12 songs in the top 10 from 1949 through 1952 Eckstine at his peak was more popular than Sinatra and Bing Crosby.  He was the first African American singer to appeared on the cover of Life Magazine.  Billy set fashion trends, and was swarmed by the bobby soxers.  Metronome magazine named Eckstine that top male vocalist in 1949 and 1950. The Down Beat readers voted him the most popular singer in 1949 and 1950. Eckstine earned 11 Gold records during his career. He is credited as a major influence in the music genres of Bop, Soul, and R&B.  Eckstine was inducted into the Big Band and Jazz Hall of Fame in 1985.

Lionel Hampton said of Eckstein: "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 our singer."

"Eckstine was a warm man who overcame racial stereotypes to succeed. He was a man of great character, of courage." Singer Nancy Wilson

"The most important thing to me as a jazz musician is that Billy Eckstine, from a historical point of view, had one of the most revolutionary big bands in jazz. "There were four big bands that changed jazz -- Earl 'Fatha' Hines, Billy Eckstine , Dizzy Gillespie and Woody Herman. Mr. Eckstine  had all those great innovators who left their marks in jazz."   - Nathan Davis, Director of jazz studies University of Pittsburgh. 

Highland Park Beginnings

Billy Eckstine was born as William Clarence Eckstein in Pittsburgh in July of 1914.  His father William was a chauffeur and his mother Charlotte was a dress maker.  The Eckstein family lived at 5913 Bryant Street in Pittsburgh’s Highland Park neighborhood.   Billy started singing at an early age when his grandmother taught him hymns.  He made his first appearance singing at a church bizarre at age 11.  He began high school at Peabody School.  When his sister Maxine got a teaching job in Washington D.C, Billy moved with her to the capital city and attended Armstrong High School.  

National Talent Contest Winner

While living in D.C in 1933 Billy won a local talent contest by imitating singer Cab Calloway earning him a chance to compete for a national prize.  Singing at the Apollo Theater in Harlem he beat Ella Fitzgerald to win the national talent contest.  In a 1952 Pittsburgh Press article it was reported that Billy won the national talent contest while in high school and then turned down a music scholarship offer from Howard University to instead become a professional singer.  In other biographies it is reported the Billy attended college at St. Paul Normal Industrial School in Lawrenceville, Virginia and won the talent contest while studying physical education for one year at Howard University in D.C.

Dance Band Leader

After leaving school Billy performed as a vocalist with small dance bands in Pittsburgh, Buffalo, and Detroit.  In Pittsburgh Eckstine led the five piece band the “Baron Billy Band" and was the vocalist and conductor of the Savoy Ballroom Orchestra".  He making $15 a working in bands and supplemented his income working as a singing waiter.  The Savoy Ballroom Orchestra was broadcast live daily over station WWSW-AM in Pittsburgh during 1933 and 1934.  Eckstine also worked shows in Chicago from 1934 until 1939. During this period he changed the spelling of his last name to “Eckstine” when a night club owner said it was “too Jewish”.   

In 1935 Billy Strayhorn, just out of high school, wrote the music, lyrics, and skits for a Cole Porter-style musical called Fantastic Rhythm that was first performed by Westinghouse high school.  It was such a success, two businessmen financed the show.  Fantastic Rhythm was a hit that played at black theaters throughout western Pennsylvania for several years. The cast included singer Billy Eckstine and pianist Errol Garner 

Tenor saxophonist Buddy Johnson heard Eckstine sing at Chicago night club and recommend him to band leader Earl Hines. In 1939 Pittsburgh's Earl Hines hired Ecktein as the singer for his Grand Terrace Orchestra. With Hines he recorded a number of hits including “Jelly, Jelly", "The Jitney Man," and "Stormy Monday."  He learned trumpet and trombone during his stint with Hines.

The Billy Eckstine Orchestra

Billy formed his own band in 1943, hiring future jazz superstars Dizzy Gillespie, Charlie Parker, and Sarah Vaughan.  He later recruited a who's who of young jazz artists including Miles Davis, Wardell Gray, Dexter Gordon, Kenny Dorham, Fats Navarro, and Pittsburgh's Art Blakey as well as arrangers Tadd Dameron and Gil Fuller. The Billy Eckstine Orchestra introduced modernist bop vocal harmonics into ballads.  They hit top ten charts with "A Cottage for Sale" and "Prisoner of Love."  Billy also played trumpet, valve trombone and guitar on the band's American and European tours. Miles David cites Billy Eckstine as his most important influence.

In his autobiography Dizzy Gillespie wrote: "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."

Pop Balladeer

Beginning in 1947 Billy became a solo pop balladeer. He recorded more than a dozen string filled hits including "My Foolish Heart", "Caravan", "Blue Moon" and "I Apologize." Occasionally he returned to his jazz roots recording with Sarah Vaughan, Count Basie, Benny Carter, and Quincy Jones.  In the 1960's he released several albums on the Motown label.  He regularly topped the Metronome and Downbeat polls in the Top Male Vocalist category: He won Esquire magazine's New Star Award in 1946;

Eckstine appeared frequently on the "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 the films Skirts Ahoy, Let's Do It Again, and Jo Jo Dancer.  

Pittsburgh World Series Hero

On his frequent visits back to Pittsburgh Eckstine went to the Crawford Grill for impromptu jam sessions.  Billy sang the national anthem for the Pittsburgh Pirates before world series games in 1960, 1971, and 1979.  They won all three of those games and all three world series.  

Billy continued to work late in his life.  In July 1991 a crowd of 10,000 turn on to see Mr. Eckstine at Hartwood Acres outside of Pittsburgh on the "Jazz Explosion" bill with Freddie Hubbard, Pittsburgh's Stanley Turrentine and Nancy Wilson.  He made his last appearance in Pittsburgh on Oct 6, 1991 when the East Liberty Chamber of Commerce saluted him with a homecoming celebration at the East Liberty Presbyterian Church.

 After suffering a stroke in 1992 while performing in Kansas he moved back to Pittsburgh to stay with his neice Mr.Carole A. Watson, and her husband, Common Pleas Judge J. Warren Watson, at their home in Schenley Heights. Eckstine died at Montefiore Hospital in Pittsburgh in 1993 at the age of 78.


Billy with Nat King Cole

Billy Eckstine House - Byrant Street Pittsburgh
Billy Eckstine on WWSW from the Savoy Ballroom
Billy Eckstine with Earl Hines

Lucky Thompson, Dizzy Gillespie, Charlie Parker, and Billy Eckstine 1944
Billy Eckstine Orchestra