Mobility is central to urbanity, and urbanity is central to our common future as the world's population crowds into urban areas. This is creating a global mobility crisis due to the unsustainability of our 20th century transportation systems for a crowded and connected world. We need to move beyond inflexible, unsustainable and brittle car-dominated mobility monocultures to flexible, sustainable and resilient mobility polycultures with a wide spectrum of integrated mobility options. This transition is hard because mobility is complex, a wicked problem and a fundamental social dilemma. In this talk, I will discuss how we can leverage the urban data revolution to resolve these challenges. In particular, I will discuss the role of next generation urban observatory science that respects complexity, embraces uncertainty and conflicting values, facilitates urban experimentation and creates environments for collaboration and knowledge co-production. I will identify the major scientific challenges, merits and broader impacts of the observatory approach to transportation and urban science.