In today’s often-tumultuous economic climate, the appeal of investment in North America’s unconventional fossil fuel “revolution” has remained both consistent and strong. In the United States, countless energy companies have focused on extracting natural gas from deposits of shale rock. In Canada, firms have sought to turn deposits of bituminous “oil sands” into a secure, domestic source of synthetic crude oil. But where, if given a choice between the two countries, might a firm otherwise indifferent to extracting natural gas or oil choose to drill? This Comment attempts to answer this question by analyzing federal, state/provincial, and local/municipal regulatory regimes in Pennsylvania, United States (home of the vast Marcellus Shale play) and Alberta, Canada (home to most of Canada’s oil sands). Ultimately, this Comment isolates three main differences between the regulatory regimes governing these two regions, and concludes that, at least in the near term, regulations in Alberta and the oil sands are more “business friendly” to potential developers than those in Pennsylvania and the Marcellus Shale.