This dissertation is a collection of research on risky behaviors such as criminal activity and substance abuse. These behaviors deserve the attention of economists because they can generate large social costs, which are often due to externalities. For example, a criminal act can generate costs not only for the offender, but for victims and for society which must expend resources on enforcement or rehabilitation. As such, it is critically important to evaluate policy and to understand the incentives created by policies either towards or away from these costly behaviors. However, as much as policy needs evaluation, it would be naive to ignore the connection between these behaviors and cultural institutions. For example, there is a well-known negative correlation between these behaviors and religious participation (Iannaccone, 1998; Iyer, 2016), and an understanding of this relationship is essential as participation changes over time. Hence, in this dissertation, I provide novel descriptive and plausibly causal estimates of the effects of both policy and institutions on costly risky behaviors.