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Frank Sinatra and Ava Gardner

Frank Sinatra and actress Ava Gardner appear at a 1955 rally in Hollywood for Democratic presidential candidate Adlai Stevenson. — Bettmann/Corbis

Frank Sinatra

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 he organized Reagan's inaugural gala two decades, and a long political journey, after he had done the same to christen Camelot.

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