The world of music has always provided fertile ground for funny nicknames. One of the best belonged to a favorite of mine — a guy who was one of the many jazz artists who thrived in both the big band era and the later modern jazz years. He was hard-partying and had a quirky sense of humor, but was always respected by his contemporaries.
John Haley "Zoot" Sims was a talented saxophonist who for many years epitomized the cool, laid-back jazz musician, but he didn't start out that way. Growing up as part of a New York family that performed in Vaudeville, young Jack Sims first learned 
to play drums and then clarinet, but took up the tenor sax after hearing Lester Young play. By the tender age of 15, he was performing professionally in Bobby Sherwood's band.
When the war started he was still too young to be drafted but continued to work regularly, and it was during this period that he picked up his nickname — but more later about that. Eventually he did get drafted, but by then he'd become a regular in Benny Goodman's band, and returned to it after his service time. For the next three decades Zoot often worked with Benny but also spent time playing with Woody Herman, Artie Shaw, Count Basie and others (video below).
As the popularity of the big bands faded in the post-war years, Zoot was able to effortlessly move into the evolving modern jazz world. Eventually he added soprano sax play to his repertoire, but his warm and accessible tenor stylings remained his trademark. Through the years he was at the center of many outstanding groups, working with Gerry Mulligan, Al Cohn and others, and generating countless first-class recordings before his death in 1985. A good example is his take on Gershwin's "'S Wonderful," which features Zoot teamed up with Oscar Peterson and guitarist Joe Pass.
But back to that nickname. So the story goes, in 1941 he was a very young 
musician appearing as part of a band show in Los Angeles, and the promoters decided to liven things up a little by putting silly nicknames on the music stands in front of the musicians. Young Jack's was Zoot, which at that time was probably most associated with the semi-respectable but very cool zoot suit.
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