Given that “sin” products must navigate different regulatory environments, it is important to compare cigarette advertising across cultures. Using text analysis, this study examined the message strategies and the ideological beliefs in cigarette advertising in American and Ukrainian magazines within the context of their different regulatory environments. The messages across the two countries differed in their use of creative appeals to ego, social needs, and sensory pleasure as well as their adherence to regulation. Many of the Ukrainian campaigns were reminiscent of earlier American campaigns and offer unique comparisons of cultures that are at different places historically, economically, and ideologically.