One in seven American households experience food insecurity at times during the year, lack of money and other resources hinder their ability to maintain consistent access to nutritious foods. Low-income, ethnic minority, and female-headed households exhibit the greatest risk for food insecurity, which often results in higher prevalence of diet-related disease. The food insecurity-obesity paradox is one that researchers have explored to understand the factors that influence food insecurity and its impact on weight change. The aim of this inquiry was to explore new evidence in associations of food insecurity and obesity in youth, adult, and elderly populations. A literature search of publication databases was conducted, using various criteria to identify relevant articles. Among 65 results, 19 studies conducted since 2005 were selected for review. Overall, the review confirmed that food insecurity and obesity continue to be strongly and positively associated in women. Growing evidence of this association was found in adolescents; but among children, results remain mixed. Few studies supported a linear relationship between food insecurity and weight outcomes, as suggested by an earlier review. New mediators were revealed (gender, marital status, stressors, and food stamp participation) that alter the association; in fact, newer studies suggest that food stamp participation may exacerbate obesity outcomes. Continued examination through longitudinal studies, development of tools to distinguish acute and chronic food insecurity, and greater inclusion of food security measurement tools in regional and local studies are warranted.