Debt is a common issue among medical residents in the United States. This review attempts 1) to evaluate the level of debt among residents, 2) to assess perceptions toward debt among residents, 3) to determine debt-management options pursued, and 4) to gauge whether levels of debt affect resident career choices. A systematic literature search of articles published between January 2012 and January 2022 in the MEDLINE, EMBASE, and Cochrane databases was performed. The combination of search terms of (financial literacy OR debt) AND (residency OR graduate medical education) were utilized. Primary outcome measures assessed were the levels of debt and perceptions toward the debt. Secondary outcome measures were debt-management options pursued and whether debt affected career choices for residents. Twenty-one studies evaluating a total of 15,585 residents were included in this systematic review. Levels of debt greater than $200,000 were not uncommon across residents and debt burdens are increasing. Greater levels of debt are associated with increased stress and anxiety. Residents reported multiple debt-management options pursued, including loan forbearance, moonlighting, income-based repayment models, military financial support, and loan forgiveness programs. Those with increased levels of debt were less likely to pursue subspecialty training and academic employment positions. The findings conclude that residents carry a substantial amount of debt, and it is a common source of stress and anxiety. Although there are many different avenues that are pursued for debt repayment, levels of debt appear to affect decisions to pursue subspecialty training and to pursue academic positions. Strategies or programs aimed at reducing the debt burden felt by residents could be of great value.