According to a recent evolutionary life history model of development proposed by Ellis, Figueredo, Brumbach, and Schlomer (2009), growing up in harsh versus unpredictable environments should have unique effects on life history strategies in adulthood. Using data from the Minnesota Longitudinal Study of Risk and Adaptation, we tested how harshness and unpredictability experienced in early childhood (age 0-5) versus in later childhood (age 6-16) uniquely predicted sexual and risky behavior at age 23. Findings showed that the strongest predictor of both sexual and risky behavior was an unpredictable environment between ages 0 and 5. Individuals exposed to more unpredictable, rapidly changing environments during the first 5 years of life displayed a faster life history strategy at age 23 by having more sexual partners, engaging in more aggressive and delinquent behaviors, and being more likely to be associated with criminal activities. In contrast, exposure to either harsh environments or experiencing unpredictability in later childhood (age 6-16) was, for the most part, not significantly related to these outcomes at age 23. Viewed together, these findings show that unpredictable rather than merely harsh childhood environments exert unique effects on risky behavior later in life consistent with a faster life history strategy. The findings also suggest that there is a developmentally sensitive period for assessing environmental unpredictability during the first 5 years of life.