Gil Evans (Ian Ernest Gilmore Green) was born May 13, 1912, in Toronto, Canada, to Margaret Julia McConnachy; his father died before he was born. As a child, Evans and his mother moved frequently throughout the Pacific Northwest,  where his mother got work as a cook in logging and mining camps in British Columbia, then in the U.S. in Idaho, Montana and Washington. She married a miner John Evans, and the family settled in California when Gil was about 8 years old. Gil attended junior high school in Berkeley. It was there that he received informal piano lessons from a friend’s father, an avid jazz fan. From here on, Gil’s interest in music grew.

The Evans family moved to Stockton, California in 1928, where Gil entered high school as a junior, and started teaching himself about music. He spent many hours practicing the piano at the homes of friends, since he didn’t own one. He also spent a lot of time listening to jazz on records and on the radio. Years later, Evans said: “When I was coming up, radio was the big thing—there were broadcasts from all over the place. Louis Armstrong came on all the time, and so did Duke and the Casa Loma Band…I caught all these broadcasts as much as I could and it was a wonderful education.” Gil was a great admirer of Armstrong: “Everything I ever learned about jazz came from Louis Armstrong-- how to handle a song and how to love music.” Evans formed his first small dance band with some school friends, playing arrangements of popular tunes that he painstakingly copied off of records.

Gil graduated from high school in 1930 and entered the College of the Pacific, Stockton, in the fall. He transferred to Modesto Junior College, a bigger school, and his band started getting more local jobs at college dances and resorts. Two years later, the band was based back in Stockton, and Gil Evans and His Orchestra, now a nine-piece band,  became a local favorite. They played regularly at a Stockton  dance hall where they made their first radio broadcasts. One of the band members was trumpet player Jimmy Maxwell, who went on to work with Benny Goodman and other prominent musicians. Maxwell described Evans’s early style: “Even then, Gil had a knack for writing for ten pieces so that it sounded like a 12 or 15-piece band. He was skillful early on at creating colors and beautiful sounds….We talked an awful lot about ‘when we were famous.’”

In the summer of 1935, the band played all summer at the Capitola Ballroom near Santa Cruz, California, and  Gil Evans became locally known as “The Prince of Swing.”  Evans modeled the band on the Casa Loma Orchestra, encouraging his musicians to double on a variety of instruments. He held rehearsals for several hours a day, and pushed his musicians to sound as good as possible. Their efforts paid off:  that fall Evans’s band was hired as the house band at the Rendezvous Ballroom in Balboa Beach, south of Los Angeles. Evans and his musicians mingled with members of famous big bands that came through, including Benny Goodman’s and Jimmy Dorsey’s.

In the fall of 1937, Gil Evans and His Orchestra went on its first tour to Northern California, Oregon and Washington, and end up staying for five weeks at the Trianon Ballroom in Seattle. In a letter to friends, Gil wrote: “Everything is going fine up here. Up until now they’ve always had sweet bands so we’re still a little worried… the main problem has been trying to establish credit in the various eating establishments.” Gil’s band subbed for Duke Ellington’s Orchestra which was scheduled at the Trianon, but had been stuck in California due to a blizzard. The ballroom’s newsletter reported: “Well over a thousand Ellington fans were turned away at the scheduled matinee… Gil Evans and his boys put on a fine program and everyone had a good time, dancing to his fine swing music.”

Through this period, Evans, even then a perfectionist about the band’s sound, turned down some offers because he thought his band “was not ready.” Other factors also contributed to the fact that Evans couldn’t find steady work for his band. He got an offer to turn over his band to vocalist Skinnay Ennis (formerly with Hal Kemp’s band); Ennis had immediate bookings, and Evans stayed on as his arranger. After a few months, the band was hired for comedian Bob Hope’s new nationally syndicated radio show, which was broadcast from Los Angeles, so Evans and some of his musicians moved there. The well-established arranger Claude Thornhill was hired as chief arranger for the show. Thornhill was classically trained musician with a flair for orchestral sonorities. Evans learned a lot about orchestration from Thornhill, and the two developed a friendship, as well.

The Hope show went on tour in 1940, and Evans visited New York City for the first time. He was thrilled to check out the jazz scene he’s heard so much about on 52nd Street. He wrote to a friend: “I saw Roy Eldridge (who is the greatest I ever heard) and Billie Holiday (who is beautiful and the greatest I ever heard).”  A few months later, Thornhill formed his own big band, and it was hired to play at the Glen Island Casino, a supper club near New York City. The club had a radio wire, and its shows were broadcast across the country. Writing  for the Claude Thornhill Orchestra, with its beautiful sounding woodwinds and French horns, had a huge appeal for Evans. “I haunted Claude until he hired me as arranger in 1941.”  This was a crucial period in Evans’s musical development, and he later said  that the Thornhill band was like a “laboratory” for him. 

World War II caused much disruption in the world of big dance bands. Thornhill enlisted in the Navy in October 1942, ending his band’s run at Glen Island. Evans was drafted the following February. Skinnay Ennis had become the leader of a privileged band unit in Santa Anita, California, and requested Evans as arranger; several other jazz musicians and arrangers were members of that band. Eventually, Evans’s shipping orders took him to Virginia, where he was an instructor in a Band Training Unit; while there he befriended Lester Young, who was in a nearby military prison.