The Singing Bandleaders

The common images of the great Swing Era bandleaders include dazzling trumpeters with gleaming horns; handsome young clarinet virtuosos; and elegant pianists conducting from the keyboard. Singers were an important part of every orchestra’s success, but few of them were bandleaders.

Bob Crosby

This week on SDPB Radio’s Big Band Spotlight we’re featuring music from a handful of the most prominent singing bandleaders, including both vocalists only and and instrumentalists who also sang.

Bob Crosby is in the former category. The younger brother of Bing, he became a bandleader when refugees from the Ben Pollack orchestra asked him to front their new band. It was a great group filled with outstanding musicians with a penchant for classic New Orleans jazz. Crosby didn’t have much to do with the band’s music, though. His role was to serve as the public face of the band. As he said years later, “I’m the only guy in the business who made it without any talent.” While he was being modest, his singing was no match for his brother’s, although he possessed the same sort of warm baritone. That tepid compliment aside, it’s only his band’s instrumental records that anyone needs to hear today.

Cab Calloway, on the other hand, was a remarkable singer who led a spectacular, hard swinging big band. Even though he didn’t play an instrument or write music, he wasn’t just an entertaining front man. Throughout the thirties and forties he filled his orchestra with such outstanding musicians as trumpeters Dizzy Gillespie and Jonah Jones; tenor saxophonist Chu Berry; bassist Milt Hinton and drummer Cozy Cole. And they weren’t stuck simply providing accompaniment to their leader’s manic hi-de-hoeing. Calloway made sure they had great arrangements to play and room to blow.

Here’s a clip of Cab Calloway and his great orchestra in a clip from the 1943 movie Stormy Weather performing “Jumpin’ Jive.” This is mostly a showcase for the phenomenal dancing of the Nicholas Brothers, but you can hear, and see, this great band in action.



Because so much of his repertoire was filled with pseudo-hep novelty songs, Calloway has rarely been taken seriously as a bandleader or a singer. It’s too bad he didn’t sing more ballads like “One for My Baby (and One More for the Road).”



Although primarily known as a smooth, ballad singer, in the mid-1940s Billy Eckstine led a startling, groundbreaking orchestra that was the first big band to play the modern jazz sounds of be-bop. Eckstine made his reputation as a singer with pianist Earl Hines Orchestra, which in 1943 included both Dizzy Gillespie and Charlie Parker. Eckstine helped lure Gillespie into the band by telling him Parker was about to join, and then got Parker by telling the saxophonist that Gillespie was coming on board. When Eckstine formed his own band the next year, he filled it with young boppers including Parker and Gillespie.

Here’s a 1946 clip of Billy Eckstine’s big band playing “Lonesome Lover Blues.” (Both Parker and Gillespie were long gone by then.) The tenor saxophone soloist is a young Frank Wess. The drummer is Art Blakey. Although Ecsktine was primarily a singer, he did play a little trumpet and valve trombone.



Singing bandleader Skinnay Ennis was well-known in the 1940s, but today is mostly forgotten. He made his name singing with Hal Kemp’s sweet band before taking over a struggling, West Coast band led by arranger Gil Evans. Under Ennis’ leadership, the orchestra became the house band on Bob Hope’s new radio show where the singer/bandleader took part in the program’s comedy routines. Ennis had a small, whispery voice as you can hear in this 1941 Soundie of his band performing a song called “Lamplight.”



Among the singing bandleaders who were also musicians was Tony Pastor. As a tenor saxophonist he played in a rather sweet style, but Louis Armstrong inspired his gravelly singing. (His voice was very similar to that of another singing bandleader of Italian heritage: trumpeter Louis Prima. They also shared a taste for Neapolitan novelty numbers.) Pastor was a long-time friend of Artie Shaw’s and was a key member of the clarinetist’s late-1930s bands before forming his own popular group.

Here’s a clip of Tony Pastor with his orchestra performing “Margie.” Pastor held on with a big band through most of the 1950s and this probably dates from the early part of the decade.



Of all the singing horn players, no one was as remarkable as trombonist Jack Teagarden (other than Louis Armstrong, of course). He had a warm, lazy, legato style of singing that matched his trombone playing. Others have observed, rather facetiously, that sometimes it’s hard to tell when he’s singing or when he’s playing the trombone. But whether singing or playing, Teagarden was always drenched in the blues.

Jack Teagarden (Photo by William Gottlieb)

As a heavy drinker with no flair for business, it’s astounding that Teagarden managed to keep a big band together for some seven years. His bands were professional, but rather anonymous – except when Teagarden opened his throat to sing or put his trombone to his lips.

In his Biographical Guide to the Great Jazz and Pop Singers, Will Friedwald makes the argument that Woody Herman was by far the best of the singing bandleaders. He wasn’t as fine a singer as Jack Teagarden, Billy Eckstine Cab Calloway or Ella Fitzerald (who fronted a band from 1039-1941), but for fifty years he led a series of remarkable bands that stayed modern and served as a training ground for an impressive number of young jazz musicians.

As a singer, Herman had a flexible voice and could sing tender ballads or shout the blues. I don’t share Friedwald’s enthusiasm for Herman’s singing and find it an acquired taste at best. I’d much rather hear Herman’s swinging clarinet or expressive alto sax, which was strongly influenced by the great Johnny Hodges.

Here’s a 1938 clip of Woody Herman singing “Doctor Jazz” with his Band That Plays the Blues (as it was billed).












This entry was posted in Billy Eckstine, Bob Crosby, Cab Calloway, Jack Teagarden, Singers, Skinnay Ennis, Tony Pastor, Woody Herman. Bookmark the permalink.

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