One of the most popular male vocalists of the late 1930s, Jack Leonard got his start singing at a roadside stand on Long Island and worked on the government relief team that built New York’s Jones Beach in the early 1930s. He was singing in Bert Block’s orchestra when Tommy Dorsey hired him away in early 1936. Dorsey also took trumpeter Joe Bauer and arranger Axel Stordahl, then known as Odd Stordahl. Together the men formed a vocal group call the Three Esquires.
It was as a soloist, though, that Leonard would achieve stardom, singing on such classics as “Marie,” “All the Things You Are,” “Our Love,” and “Indian Summer.” He quickly became popular with audiences and critics alike and placed at or near the top in various polls conducted during the late 1930s. He was rivaled only by Bing Crosby in popularity.
Leonard was a shy, handsome man who was liked by all. He was very near-sighted but refused to wear glasses in public so as not to spoil his romantic image. His departure from Dorsey’s orchestra in November 1939 was a surprise to his bandmates. The rumor was that Dorsey had grown suspicious of Leonard’s intentions, fearing that he was going to leave soon for a solo career, and had forced him out. Leonard himself tried to dispel that rumor at the time, saying he just needed a break and would return soon, and indeed an announcement was made a week later that Leonard and Dorsey had patched up their differences and that Leonard would return to the band permanently. He never did.
Dorsey had just lost his other long-time vocalist, Edythe Wright, the previous month and used the opportunity of shedding Leonard to revamp his entire orchestra, which may have also played a part in the singer’s departure. An unusual quirk in the matter was that Dorsey held Leonard’s personal management contract, meaning that he would get a cut of anything Leonard made as a solo artist. Leonard was replaced in Dorsey’s band by Allan DeWitt, who failed to work out and was replaced after less than two months by Frank Sinatra.
Early Solo Career and War Years
Leonard’s popularity kept him busy after leaving Dorsey. He worked steadily on radio, appearing three times a week on CBS. When Leonard wasn’t on the radio he was either in theaters or in the recording studio for Okeh Records. He also began dating singer Amy Arnell. His career and personal life were going strong until early March 1941, when, on the same day that he screen-tested for 20th Century Fox and signed on for appearances at New York’s Paramount Theater for $350 a night, Leonard received his draft notice. He managed a deferment until May to complete his Paramount obligations and then reported for duty. His draft board proposed putting him in an Army entertainment unit, though Leonard refused. He ended up singing anyway, at Fort Dix, New Jersey, for the Herbie Fields band.
Leonard’s initial period in the Army had little effect on his popularity. Soon after he entered the service, Okeh gained permission to bring him into the studio while he was in uniform, which helped keep his name in circulation. The Army then released him in November, before his year was up, because he was over 28 years old, and he quickly returned to civilian life and resumed his career, beginning a series of theater dates and cutting several more sides for Okeh. He was also in the running for his own NBC radio program. In the wake of Pearl Harbor, though, the Army recalled him to active duty in January 1942, and back to Fort Dix he went, this time for the duration of the war.
Popular with other soldiers, Leonard rose to the rank of staff sergeant. He soon found himself fronting his own band, which kept him busy hosting a nightly variety show and doing four radio broadcasts a week, including one for the Mutual network. The band traveled to Europe in early 1945, returning in August for reassignment. Discharged soon after, Leonard attempted to restart his career after five years of inactivity.
Before Leonard had even received his discharge papers, networks had begun feeling him out for a radio program. In December, he signed a two-year deal with Majestic Records, and his first live booking happened on January 3 at the Copacabana in New York, where he took second billing after Jerry Lester when Phil Regan refused to accept the spot. There was great expectations for Leonard among audiences and critics, but he would soon disappoint. His 1946 recordings sounded similar to the romantic ballads of his pre-war material but lacked warmth, and when they failed to capture any attention 1947 saw a complete shift in style to light-hearted material backed by a jazzy vocal quartet, which equally failed to impress.
Leonard made three minor silver screen appearances starting in 1947, his first as a singing cowboy in a film titled Swing the Western Way. All were B movies. Majestic dropped him after his contract ended, and he signed with Hi-Tone in 1949 and also recorded with Signature later that year. The records received little notice. He had his own television program in 1949, and appeared as one of the hosts for Broadway Open House in 1951, but despite his best efforts he was never able to regain the traction he had prior to the war.
Leonard made a return to the recording studio with Dorsey in 1951. The bandleader arranged the sessions as a way to help boost Leonard, but the records, old-fashioned in their attempt to mimic their 1937 hit “Marie,” went nowhere. When Dorsey offered Leonard the job of advance radio promotion man for the band in 1952, Leonard accepted, retiring from the stage. Leonard’s duties were to precede the band into town at their next scheduled performance and hit the airwaves to promote the show, a job that he loved. He only occasionally sang thereafter, most notably in 1956 when he performed at the memorial concert after Dorsey’s death.
Leonard later served as Nat King Cole’s business manager and worked in music publishing before retiring in the 1970s. He married Edna Ryan in July 1948. Jack Leonard died from cancer in 1988, age 75.
It’s an oft-repeated falsehood that Sinatra replaced Leonard in Dorsey’s band. The story is also sometimes told that Leonard left Dorsey because he was drafted, which is even less true. The events that surrounded Leonard’s departure from the orchestra were major news events and clearly reported at the time but became distorted by the late 1940s, with even trade magazines and jazz “historians” misremembering the correct story. Leonard himself tied into this narrative, and these falsehoods have been perpetuated over the years by newspaper articles, obituaries, and sloppy historical work. ↩︎
The date of Leonard’s birth is usually given as 1915, and obituaries say he was 73 when he died in 1988. His grandson, however, has stated that Leonard’s birthdate is February 10, 1913, and both Down Beat and Billboard magazines reported that Leonard had been discharged from the service in November 1941 because he was over 28 years old, which validates the 1913 birth year. Leonard most likely, when he was attempting to resurrect his career post-war, misrepresented his age to appear younger, a not uncommon practice for celebrities at that time. ↩︎