The political gulf between them may have been wide, but conservative icon William F. Buckley and the left-wing Norman Mailer cut remarkably parallel tracks through the 1960s. Both wrote best-selling first books (Buckley’s God and Man at Yale and Mailer’s The Naked and the Dead). Both founded important periodicals (National Review and The Village Voice, respectively). Both ran for mayor of New York.

They argued publicly about every major issue of the decade—the counterculture, Vietnam, feminism, civil rights, the Cold War—but behind the scenes were friends and confidantes.

University of Illinois at Chicago historian Kevin M. Schultz discusses his revealing new book about two towering figures who served as the Sixties’ ideological bookends.