In this article, I aim to explore how legitimization and de-radicalization of the underground hip-hop subculture have restrained the DIY creation of social norms and cultural behaviours that mobilized Iranian hip-hop in the early 2000s. The article offers a critical discussion of the literature around legitimization of DIY/underground subcultures, specifically youth musical subcultures such as punk and hip-hop, before turning to an analysis of Iranian hip-hop culture in three phases: (1) hip-hop and the creation of a community, 2000–2003; (2) the golden age of Iranian hip-hop, 2003–2009; (3) contemporary Iranian hip-hop, 2009–2016. The article suggests that these three phases have finally led to the entry of hip-hop into the mainstream system and cultural industry, as recent trends bringing it in line with the values and standards of Islamic Iran result in turning underground DIY culture into a mainstream popular form of music supported and funded (indirectly) by the Islamic state.