Children who experience parental imprisonment report greater mental and physical health adversities in adolescence and adulthood relative to comparable individuals whose parents did not serve time in prison. Research has linked BMI gain with parental imprisonment among females, but other studies have shown null or negative associations between parental imprisonment and weight increases for their offspring. Using longitudinal data from the National Longitudinal Study of Adolescent to Adult Health, this study attempts to resolve these differential findings by examining the interrelationship between delinquent behavior and BMI associated with parental imprisonment as individuals progress from adolescence into adulthood (ages 12–32). We show that higher delinquency levels are associated with lower BMI among men and women. With the transition from adolescence to adulthood, parental imprisonment is linked with increased BMI gain and obesity among females who are not delinquent. These findings highlight the need to consider how the decline in delinquent behavior and increasing health disparities between adolescence and adulthood may intersect as individuals experiencing parental imprisonment transition from adolescence to adulthood.