This article assesses the applicability of subcultural theories to individual cases of jihadi and Right-wing radicalization in Germany, with a focus on the individual initial situation and motivation for involvement. Within an overall qualitative research design, the article tests deviance/strain and Centre for Contemporary Cultural Studies (CCCS) subcultural theories against four jihadi and three Right-wing extremist cases. The findings show little support for the strain-based status frustration hypothesis, but confirm the illegitimate opportunity structure thesis; modified versions of the CCCS’ resistance, bricolage, and homology concepts; as well as some of the postmodern approaches to agency and cultural cross-fertilization. The jihadi and Right-wing radicals examined here are assertive and purposive agents, strategically using the rich cultural arsenal available in the mainstream and/or other subcultures, while at the same time being themselves influenced by contemporary mainstream preferences of style. The article discusses the implications of these findings for radicalization research and specific subcultural approaches. It argues for a greater focus on both individual agency and the (sub-)cultural context for an improved understanding of individual involvement in political violence.