Frank Sinatra has always been a contradictory figure. Biographers have often commented on the paradoxical nature of Sinatra's personality, attempting in vain to reconcile the sensitivity, subtlety, and stark emotionality demonstrated by one of the 20th century's foremost interpreters of popular song with the image of the violent, boorish, and insensitive thug that denned his offstage persona. The more politically minded of his biographers have also commented on his radical political swing from fellow traveler of the Communist Party to right-wing ideologue over the course of his 50-plus-year career (though whether one wants to count the last twenty years or so of it as a defensible “career” rather than an extended exercise in ill-advised self-indulgence is another matter). They have attributed this shift either to Sinatra's fury at being first courted and then slighted by the Kennedy administration, which after the 1960 presidential election smartly distanced itself from Sinatra's mob ties, or to his visceral hatred of rock 'n' roll and, by extension, the counterculture for which it provided the sound track and of which it was a partial expression. While these explanations are convincing on the level of psychobiography, they miss the larger cultural scope of the political contradictions that shaped Sinatra's career — contradictions that lend his career an allegorical significance in charting the expressions and transformations of political community formation in the mid-20th-century United States. That this allegorical significance extends beyond the caprice of the cultural studies analysis that follows is suggested by Sinatra's enduring popularity as a national icon.