We compare four different risk-taking propensity measures on their ability to describe and to predict actual risky behavior in the domain of health. The risk-taking propensity measures we compare are: (1) a general measure of risk-taking propensity derived from a one-item survey question (Dohmen et al., 2011), (2) a risk aversion index calculated from a set of incentivized monetary gambles (Holt & Laury, 2002), (3) a measure of risk taking derived from an incentive compatible behavioral task—the Balloon Analog Risk Task (Lejuez et al., 2002), and (4) a composite score of risk-taking likelihood in the health domain from the Domain-Specific Risk Taking (DOSPERT) scale (Weber et al., 2002). Study participants are 351 clients of health centers around Witbank, South Africa. Our findings suggest that the one-item general measure is the best predictor of risky health behavior in our population, predicting two out of four behaviors at the 5% level and the remaining two behaviors at the 10% level. The DOSPERT score in the health domain performs well, predicting one out of four behaviors at the 1% significance level and two out of four behaviors at the 10% level, but only if the DOSPERT instrument contains a hypothetical risk-taking item that is similar to the actual risky behavior being predicted. Incentivized monetary gambles and the behavioral task were unrelated to actual health behaviors; they were unable to predict any of the risky health behaviors at the 10% level. We provide evidence that this is not because the participants had trouble understanding the monetary trade-off questions or performed poorly in the behavioral task. We conclude by urging researchers to further test the usefulness of the one-item general measure, both in explaining health related risk-taking behavior and in other contexts.