The characters of David's Halberstam's The Fifties comprise an enormous range of diverse individuals ranging from political leaders (such as Harry Truman, Dwight Eisenhauer, and Richard Nixon) to titans of industry (McDonalds's founder, Ray Kroc) to novelists and poets (Jack Kerouac and Allen Ginsberg). The characters are woven into a broad historical tapestry to show how in modernity, culture and commerce shape history as much as political and military developments.

Richard Nixon

Halberstam's method of historical characterization entails an anecdotal and personal style rather than a more detached approach. He frequently creates psychological portraits of individuals and then attempts to suggest ways in which individual psychology reflects historical conditions of the time. For example, in his portrait of Richard Nixon, whom he sees as a figure who embodies the conflicts of the era, he depicts Nixon as being both angry and vengeful but also full of potential.

Jack Kerouac and Allen Ginsberg

Halberstam's portraits of Jack Kerouac and Allen Ginsberg show a similar habit of using contrast as a means of characterization. Thus, we are presented with a portrait of Kerouac, whose promise is undone by his addiction to alcohol and the destructive influence of fame, and a portrait of Ginsberg as a loner turned celebrity.

Klaus Fuchs, J. Robert Oppenheimer, Marilyn Monroe, and others

As he surveys a sweepingly broad historical canvas, the mixed cast of characters—including, notably, Klaus Fuchs (the double agent for the USSR who disclosed nuclear secrets), J. Robert Oppenheimer (the mastermind behind the nuclear bomb), and doomed actress Marilyn Monroe—all make appearances as personally conflicted, accessible yet elusive, public yet private figures. Halberstam does not invest in tragic portraits of these historical characters, yet he does stress complexity and historical contingencies in the shaping of character. In the end, it is technology, as much as character, that places a determinative role in shaping historical events such as the development of the nuclear bomb. Yet behind every novel technology, Halberstam shows, lies a web of competing human interests and social exchange between deeply flawed individuals.