Now more than ever, organizations are leveraging the power of games and play to provide greater agility in an increasingly complex business environment. Games are the perfect medium for engaging a large number of people in experimentation, process optimization, strategy, empathy, and decision trade-offs; all characteristics critical to success in today's business environment. Since IBM introduced its cognitive computing service Watson, we have begun to play around with how this innovation can impact serious games and the engagement problems our applications solve for enterprises. The results have been profound! In this talk, we will discuss how games can contextualize big data through play and cognitive computing. We will show you how other game developers have worked with IBM to create applications that take engagement to the next level and how this journey is just beginning!