A focus on masculinity and crime has been an ongoing feature of popular culture, ranging from early pulp fiction, cartoons, popular music, commercial film and television, and contemporary forms of gaming and online media. In sociology and cultural studies, the search for unequivocal examples of ideological repression has been thrown into doubt by accounts that seek out nuanced readings of cultural depictions and that have reworked evidence from audience research to question ideology as an uncontested absorption of ruling ideas. The creative relationship between producer and audience, with shifting meanings for consumers of culture, means a hesitation about whether cultural items can be read as holding a single inner meaning. A consideration of these cultural forms shows that simpler depictions of crime and criminal justice as a terrain of symbolic struggle between rival masculinities contrast morally repellent offenders from law enforcement heroes who enact justice and guard society. Yet cultural accounts of crime often offer more ambiguous scenarios that are difficult for viewers to judge, and opportunities for viewers to identify with acts of violence and lawbreaking that play on the wider tensions between official state-based and outlaw “protest” masculinities in the criminal justice system.