This paper reviews Creative Economy theory and practice and attempts to intersect the author’s findings with Sustainability Planning and Development theory and practice. An extensive literature review, including over 40 publications (articles, reports, white papers, conference proceedings and books) as well as interviews, personal observations and website reviews was used to develop this paper and the author’s conclusions. Current Creative Economy and Sustainability theories are explained and analyzed as well as the role of the artist, the entrepreneur, the city and cultural organizations. The author provides recommendations for the City of Portland, Maine and concludes that the qualitative benefits of the non-commercial creative economy such as clean air, beauty, cross-cultural communication, and community capital must be balanced with the predominant efforts geared toward developing the quantitative benefits of the creative economy’s commercial sector and measures of GDP