The practice of selling single cigarettes (loosies) through an informal economy is prevalent in urban, low socioeconomic (low SES) communities. Although US state and federal laws make this practice illegal, it may be occurring more frequently with the recent increase in taxes on cigarettes. This investigation provides information concerning the illegal practice of selling single cigarettes to better understand this behavior and to inform intervention programs and policymakers. A total of 488 African American young adults were recruited and surveyed at two education and employment training programs in Baltimore City from 2005 to 2008. Fifty-one percent of the sample reported smoking cigarettes in the past month; only 3.7% of the sample were former smokers. Approximately 65% of respondents reported seeing single cigarettes sold daily on the street. Multivariate logistic regression modeling found that respondents who reported seeing single cigarettes sold on the street several times a week were more than two times as likely to be current smokers compared to participants who reported that they never or infrequently saw single cigarettes being sold, after controlling for demographics (OR = 2.16; p = 0.034). Tax increases have led to an overall reduction in cigarette smoking. However, smoking rates in urban, low SES communities and among young adults remain high. Attention and resources are needed to address the environmental, normative, and behavioral conditions influencing tobacco use and the disparities it causes. Addressing these factors would help reduce future health care costs and save lives.