The 30th Anniversary Playboy Jazz Festival was held this weekend at the Hollywood Bowl in Los Angeles. It was first held in Chicago Stadium in 1959. After a twenty year lapse, it was resurrected again in 1979 at its current venue in L.A.

On hand to take in the entertainment were Hugh Hefner and his favorite women, Holly Madison, Bridget Marquardt and Kendra Wilkinson. The emcee for the event since 1995 has been Bill Cosby.

The 82 year old founder and majority owner of Playboy Enterprises looks as if he might be auditioning for Gilligan’s Island in his captain’s hat. Hefner made news a while back when he offered a magazine pictorial to 15 year old Miley Cyrus. Hefner said she was a “pretty lady” but would have to wait until she was 18 to appear in the magazine. This followed closely on the heels of her controversial Vanity Fair photo shoot.

Check out more photos from Playboy Jazz Festival below including Bill Cosby on drums.

Photos: WENN

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Filed under: Celebrities, hugh hefner