The Playboy Jazz Festival is an annual event sponsored by Playboy Enterprises to celebrate jazz as well as feature both established and up and coming musicians of the genre. It was founded by Hugh Hefner and was first held in Chicago, Illinois at the Chicago Stadium in 1959. However, the second festival did not occur until 1979 when it was moved to the Hollywood Bowl in Los Angeles. The event has been held there ever since.
The Festival is held on a Saturday and Sunday in mid-June. Bill Cosby was the emcee of the majority of the annual festival from 1979 to 2012. In 2013, comedian George Lopez hosted for the first time, and will do so again in 2014.