Hugh Hefner in Entourage

Hugh Hefner

Mr. Hefner and the Hef girls make a short cameo when the crew visits the Playboy mansion in the second season’s third episode. After an incident during his last visit, Mr. Hefner serves Johnny Drama a lifetime mansion ban so ironclad that even superduo Shauna Roberts and Ari Gold struggle to get it lifted. About five months after his appearance on Entourage, Hef offered another HBO cameo during the fifth season of Curb Your Enthusiasm.