Jazz came to the Bowl for the first time in 1936 with clarinetist Benny Goodman. His appearance stirred controversy – was this type of popular entertainment appropriate in the Bowl? It would take another seven years before Frank Sinatra's successful appearance with the Los Angeles Philharmonic paved the way for popular artists of all styles to become an intrinsic part of Hollywood Bowl's annual Summer Festivals.

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A succession of jazz greats began appearing at the Bowl. Duke Ellington and His Orchestra, Lena Horne, Stan Kenton and Jo Stafford headlined concerts in the 1940s. Nat "King" Cole appeared annually at the Bowl from 1954–1960. The legendary jazz singer Billie Holiday appeared at the "Festival of the Americas" in 1955. A 1956 program starring Ella Fitzgerald and Louis Armstrong became the first jazz recording at the Bowl. The Verve release also featured Art Tatum and the Oscar Peterson Trio.

Big Bands appearing at the Bowl include the Count Basie Orchestra, the Tommy Dorsey Orchestra,the Duke Ellington Orchestra, the Clayton-Hamilton Jazz Orchestra, and Wynton Marsalis and the Lincoln Center Jazz Orchestra. Small jazz ensembles include the combos headed by Miles Davis, George Shearing, Dave Brubeck and many others. Jazz vocalists who were regularly featured at Hollywood Bowl include Ella Fitzgerald, Cleo Laine, Carmen McRae, Sarah Vaughan, Joe Williams, Mel Tormé, Peggy Lee, Lena Horne, and many others.

The first Playboy Jazz at the Bowl event took place in 1979. The following year, the Bowl launched its own jazz series, Jazz at the Bowl. Another annual event, JVC Jazz at the Bowl, began in 1985 as a showcase for contemporary jazz.

Reba McEntire, South Pacific, 2007. Los Angeles Philharmonic/Matthew Imaging.