Glen Gray played saxophone in a group that performed at the Casa Loma Hotel in Toronto in 1928. The group was incorporated as a co-op in NYC in 1929 as The Casa Loma Orchestra and began recording for Okeh.

In the early 1930s, the Casa Loma Orchestra was one of the bands that helped pave the way for the rise in popularity of big band swing, gaining recognition especially with the college age crowd, and wowing audiences at Yale, Dartmouth and other Ivy League schools. It is said to have been the first white big band with a deliberate Jazz policy. Although they played in a rather stiff and precise style, The Casa Loma Orchestra helped spread the concept of big band jazz to a generation of young white kids who were, at that time, still largely unaware of the great black jazz orchestras.

The Casa Loma Orchestra began to be billed under leader Glen Gray’s name in 1935, recording for Decca until 1942, and later for Mercury until 1946. While the early swing of Glen Gray’s Casa Lomans’ may sound outdated today, the band’s late 1930s and early 1940s recordings like Stompin’ Around, Come And Get It, Malady In F, Zig Zag,Swingtonic, and No Name Jive are still great listens today. Two of the bands biggest records were ballads;For You as sung by Kenny Sargent and the group's theme Smoke Rings. In 1940 Glen Gray was one of the winners, as a bandleader, in Down Beat's All American Musicians Poll.

After he stopped touring, around 1950, Gray began a series of recordings for Capitol mainly recreating hits of the big band era. Although the albums were commercially sucessful at the time,they left little room for improviation, and held few suprises. 

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