Playboy publisher Hugh Hefner might love jazz almost as much as he loves blondes, which is why the Playboy Jazz Festival at the Hollywood Bowl has become an enduring tradition. The big show, which celebrates its 35th anniversary this year, is considered one of the West Coast’s premier jazz festivals, having featured legends such as Miles Davis, Count Basie and Dizzy Gillespie and contemporary stars Wynton Marsalis and Jamie Cullum. This year’s program, June 15–16, offers 20 performances from some of the genre’s finest. Headliners are George Duke, with special guest Jeffrey Osborne; Naturally 7 with guest Herbie Hancock; Sheila E.; and Bob James and David Sanborn. Additional performers include Indie.Arie. Comedian George Lopez presides as new master of ceremonies. Take it all in at the amphitheater that Pollstar voted best outdoor concert venue in the world—smoking jacket not required. 2301 N. Highland Ave., Hollywood, 323.850.2000. playboyjazzfestival.com