Longtime Hollywood producer and former music executive Jerry Weintraub has died at 77, reports TMZ. Weintraub was best known for producing The Karate Kid franchise as well as the Ocean’s Eleven trilogy. Prior to his foray into Hollywood, Weintraub was a major presence in the music industry, having managed or promoted some of the world’s biggest names, including Frank Sinatra, Bob Dylan, Elvis Presley, Dolly Parton, and more. Over the course of his nearly 15-year friendship with George Clooney, he also ended up the butt of several of Clooney’s infamous practical jokes. A few highlights include: having a penis drawn on Weintraub’s luxe gold silk shirt (which Clooney hated); a 4:30 a.m. hotel wake-up call courtesy of Clooney’s convincing Weintraub impression; and having Clooney attack him mid-massage — a story he gleefully retold on The Ellen DeGeneres Show in 2011, which you can watch below.