The aim of this chapter is to investigate how social media help create and diffuse popular music in Saudi Arabia and how such music questions the officially accepted identities and social practices. Social media are widely used as means of promotion among artists around the world; yet Saudi Arabia deserves special attention. This is because traditional media act much more strictly as gatekeepers in the kingdom; hence, social media offer greater possibility for circulation of popular entertainment, especially when it touches upon the questions related to the core values of the Saudi society. Such is the case of recordings by Hesham Fageeh “No woman, No drive” (2013) or the recently trending video clip “Hwages” that, both, received peak visibility online and sparked debates about women empowerment. Similarly, some videos trending online prompted a dance craze, for instance, “Barbs” showed a choreography that was subsequently copied by fans who uploaded their performances online. Dancing is a prohibition among the conservative segments of society; yet, the vastly young population of Saudi Arabia seeks entertainment.Social media in Saudi Arabia have become primordial means of communication in the kingdom with highest rates of social media participation in the Middle East and seventh rank in the world (2016). Consequently, this chapter employs a mixed-method approach in order to uncover how social media breaks the monopoly on entertainment by promoting different musical genres and encouraging social debate.