This paper addresses the power and politics of contentious creativity in Saudi Arabia. I examine the ways in which artists navigate and extend the boundaries of what is permissible under the constraints of overwhelming state power, state prohibitions on expression, and often times, state financial support for the arts. The state underwrites many endeavors yet the results sometimes challenge the state turath industry. My objective is to elicit the tension between art as dissent and art as a cooptive valve. The importance of artistic expression mushroomed over the last ten years in Saudi Arabia. You Tube videos especially expressed the resentment of many marginalized citizens and foreign residents. Stand up comics and hip-hop musicians quickly cultivated a mass following. Now, however, there is an explosion of creative and critical expression in all forms across the country. Significant debates are underway and are articulated in the wider realms of art, music, dance, comedy, film and leisure. I suggest, on one hand, the state encourages art to buttress its international image and to deflect domestic attention from difficult, explicitly political debates. On the other hand, artists push the boundaries of behavior and opinion and offer new social scripts that provide ways to communicate displeasure with the status quo. There is a cat and mouse game unfolding between state powers and divergent social forces through artistic endeavors. I also explore fraught encounters at the edges of expression and how such encounters appear to intersect with class, gender and ethnicity, e.g., the harassment of a foreign boy dancing the macarena in the street; the damage done to the speakers of a Malaysian band or resentment felt by unemployed Saudis at investment in art and leisure rather than in jobs and infrastructure. This analysis draws on authoritarian transitions, social movement and critical art studies. I utilize songs and visual arts that could be interpreted as provocative or politically salient. (It does not address social media.) The changes in Saudi Arabia are indeed significant. Too often overlooked, however, is the reality that only religious privilege and conformist social norms are being addressed. Social openings may be easier than economic agendas like taxation and less public employment. The reality is that any revision in the distribution of political power is still off limits. That is why it is critical to analyze artists in various mediums who are pushing the envelope ever closer to questions of political power.