Portland: Quest for the Livable City is a documentary film and educational outreach project produced as a collaboration of the Lincoln Institute of Land Policy and Northern Light Productions. Incorporating historic footage of Portland’s growth as the self-proclaimed “City that Works,” and recent interviews with city leaders and neighborhood residents during the battles over ballot measures on the land-use planning system, this one-hour documentary film chronicles the complex challenges of aspiring to be a more sustainable metropolis with a smaller carbon footprint. As cities across the country today attempt to reduce greenhouse gas emissions, invest in transit, and focus on infill redevelopment as an alternative to car-dependent sprawl, the experience of Portland provides a cautionary tale for planning in the 21st century, involving issues of economic development, gentrification, local food and farming, property rights, and civic participation.