Background: Tattoos have reached broadening mainstream acceptance. Medical professional societies have noted that tattoos may co-occur with high risk behaviors. Methods: Using a variety of statistical models applied to a sample of 2,008 adults residing in the United States via Amazon's Mechanical Turk, we estimate the associations between tattoo characteristics, three health-related outcomes (overall health status, ever diagnosed with a mental health issue, sleep problems), and three risky behaviors (current smoking, ever spent time in jail or prison, and number of sex partners). Results: We find that the presence, number, and specific features of tattoos are positively correlated with two of the health-related outcomes (ever diagnosed with a mental health issue and trouble sleeping) and all three of the risky behaviors (P <.05). Magnitudes are larger for those with multiple, visible, and offensive tattoos. Conclusions: Our results suggest that individuals with tattoos are more likely to engage in risky behaviors relative to their non-tattooed counterparts, which may lead to health consequences. Dermatologists, healthcare providers, and public health advocates should recognize that having a tattoo(s) is a potential marker for mental health issues and risky behaviors.