In this article, we explore why the bad boy is a popular archetype inadvertising, erotica, fashion, journalism, movies, songs, television serials, andother forms of commercial culture. First, we interpret the bad boy as acombination of juvenile masculinities (aggression, rebellion, hypersexuality),appealing qualities (charisma, ruggedness, sensitivity), and moral ambiguities(via confusion, contradiction, and cumulation), which keep audiencesengaged. Second, we trace the evolution of these meanings in over acentury of American popular culture. Third, we reveal the many commercialfaces of the bad boy in the contemporary marketplace, including as anarchetypal brand positioning strategy, a transformative protagonist in eroticfiction, an unapologetic voice for macho fantasies, a beguiling object ofirrational love, a journalistic frame for polarizing masculinities, and aninexhaustible source of dramatic tension. In the final analysis, the bad boyarchetype is a contemporary marketplace icon because it has historicallybeen good at channeling all kinds of bad.