Hip-Hop music is bigger than ever, a development that some states watch with Argus eyes. The latter is especially the case when the content that hip-hop artists produce is critical towards the circumstances in their country. In various cases, regimes subsequently attempt to repress and silence these critical hip-hop performances and artists. It is that phenomenon that this study explores, trying to find an answer to the conundrum of why some regimes employ hard repressive measures to silence critical hip-hop whereas other states use soft repression. The lens of questioning what regime type a country has, will be used in order to try to uncover the answer. Due to regime type specific characteristics, it is expected that autocratic and democratic regimes use soft repressive measures, while hybrid regimes employ hard repression. This hypothesis is tested by using the method of Structured Focused Comparison and scrutinising the cases of Spain, Russia and China. Repression of critical hip-hop seems to vary a lot between cases and is rather haphazard. Hence, regime type does not seem to be the catalyst behind a certain form of repressive behaviour towards hip-hop. Instead, a variety of country specific factors seems to determine the course of repression.