From Frank Sinatra’s early pro-Zionist rallying to Steven Spielberg’s present-day peace-making, Hollywood has long enjoyed a ‘special relationship’ with Israel. Based on a newly-published book by Columbia University Press, this paper outlines the ways in which Hollywood’s moguls, directors, and actors have supported or challenged Israel for more than seven decades, including Eddie Cantor, Kirk Douglas, Elizabeth Taylor, Barbra Streisand, Vanessa Redgrave, Arthur Krim and Arnon Milchan. The paper probes the influence of Israeli public diplomacy on Hollywood’s output and lobbying activities, but also highlight the limits of ideological devotion in high-risk entertainment industries. It demonstrates how show business has played an important role in crafting the U.S.-Israel alliance and illuminates how U.S. media and soft power have helped shape the Arab-Israeli conflict.