In 1993, a new trend of memoirs began to emerge in the United States, exploring contemporary street gang life in the ghettos and barrios. The first memoirs in this cycle form the subject of this paper: Sanyika Shakur’s Monster and Luis Rodriguez’s Always Running. There have been polarised debates about such texts which have been variously demonised as violent and sensationalist or, by contrast, praised as offering a pedagogic and preventative anti-gang stance. Such contradictory responses are reflected in the memoirs themselves, emphasising the frisson of violent gang exploits and the sober, salutary reflection of politicised and educated hindsight. The memoirs developed an extensive life in the media, becoming a site for channeling charged discussions about youth, crime, race, and violence, opening up a series of discourses about black/Mexican masculinity, censorship, celebrity, and cultural commerce. This paper seeks to understand how these popular narratives, with their charged themes and topical content, came to be interpreted by commentators.