A powerful actor known equally for his off-screen volatility and his on-camera intensity, Penn has staked out a position along, and sometimes over, the left flank of the political debate. Abroad, he has visited Iran and Cuba and befriended Venezuela’s Hugo Chavez; at home, he has been more likely to show up with Ralph Nader than with mainstream Democrats. His causes have ranged from opposition to the 2003 Iraq invasion to support for gay rights. Penn’s influence, though, has come less from his vanguard political pronouncements than from the example he has set through his personal engagement with gritty challenges. He joined reconstruction efforts after Hurricane Katrina and established a relief organization in the wake of the 2010 Haiti earthquake, eventually enlisting as the manager of a refugee camp serving thousands of displaced people. Through such efforts, Penn has helped to set a modern model for Hollywood activism that prizes direct action over lobbying Congress or embellishing campaign rallies. He has demonstrated that the best way to get in the door on Capitol Hill is to arrive with mud on your shoes.
Politics was always very personal for “the Chairman of the Board,” who started his career as an FDR liberal and ended it as a Ronald Reagan conservative. Reared in a tough, racially mixed New Jersey neighborhood (by a mother active in the local Democratic Party), Sinatra brought to his political engagement a straightforward New Deal populism that viewed Democrats as the party of “the little man.” He fell hard for FDR in 1944 and campaigned for every Democratic presidential candidate over the next quarter-century. Although often crude and even brutal in his personal relationships, Sinatra also showed an early sensitivity to civil-rights issues. Still wiry and imperially slim in 1945, he starred that year in a short film (and sang the title song for) The House I Live In—a plea for racial and ethnic tolerance that won a special Academy Award. In 1961, he gathered his glittering Rat Pack for a Carnegie Hall fundraiser for Martin Luther King Jr. Sinatra’s closest political connection was with John F. Kennedy, who brought to politics the same wry and icy cool that Sinatra embodied in entertainment. Sinatra’s services for Kennedy ranged from campaign appearances to recording his campaign anthem (Sammy Cahn’s politically tweaked version of his “High Hopes”) to organizing the glitzy inaugural gala that helped retire the party’s campaign debt. But Sinatra’s less savory associations—particularly with a Chicago mobster whose mistress Sinatra also introduced to JFK—compelled the president (under pressure from J. Edgar Hoover) to sever his relations with the singer. After the break, a crestfallen Sinatra eventually moved to the right, endorsing Richard Nixon in 1972 and campaigning extensively for Ronald Reagan in 1980. In perfect symmetry, he organized Reagan’s inaugural gala two decades, and a long political journey, after he had done the same to christen Camelot.
Long before he was a politician, Reagan was a political force. As president of the Screen Actors Guild, and as a founding California member of Americans for Democratic Action, Reagan after World War II was a pillar of Hollywood’s anticommunist left—the embattled New Deal liberals who sought a political home between the communist-influenced Popular Front organizations and the archconservative Red hunters who persecuted them. But that was just a way station for Reagan on a journey that carried him rightward for the remainder of his life. After endorsing Harry Truman (the quintessential ADA liberal) in 1948, Reagan jumped the divide to support Republican Dwight Eisenhower in 1952 and never really looked back. From the moment Reagan made another leap from celebrity activist to California gubernatorial candidate in the 1966 race, his opponents tried to use his Hollywood background to discredit him. (In one 1966 radio ad, Gene Kelly declared, “I know I could play the role of a governor but that I could never really sit in his chair.”) In fact, millions of voters, first in California, then nationwide, had no trouble envisioning Reagan in the big chair, partly because of the skills before the camera that he honed in Hollywood, but more important because he projected a sense of conviction and optimism that reflected some of the nation’s deepest beliefs and most-cherished myths. Reagan’s rise to the presidency offered the kind of irony that somehow seems more appropriate to a foreign film: Hollywood has leaned left since FDR, but its most important political export proved to be a heartland Republican who redefined and reinvigorated modern conservatism.
Compared with most celebrity activists, Redford took a measured path into politics. He didn’t become engaged until after he became a breakout star as Paul Newman’s sidekick in Butch Cassidy and the Sundance Kid, and even then he first undertook a local issue (blocking the building of a highway through a canyon near his Utah home). From that initial seed blossomed decades of involvement in environmental causes; no film star has been more closely identified with the green movement. Like Warren Beatty, Redford has always seemed keenly aware of the public’s limited tolerance for instruction from entertainers. At times, that’s led him, again like Beatty, to prefer an off-screen role in his activism—as he did during the Reagan presidency in organizing quiet conferences that convened environmentalists and industry leaders, with mixed success, to bridge their differences. But in recent years, Redford has again played a more visible and, at times, confrontational part: After the BP oil spill last spring, he recorded a bristling five-minute video for the Natural Resources Defense Council in which he declared, “When I hear some of the energy companies advertising themselves as conservationists … I want to throw up.”