We examine effects of the Crack Cocaine Era on two generations of females. Interviews were conducted (1996-2001 for separate National Institute on Drug Abuse-funded projects) with 58 women and 24 girls born into distinct drug eras (Crack Generation and Marijuana Generation). Using attachment theory as a framework, we analyze each cohort’s drug involvement and family relationships. Women’s crack use contributed to disrupted attachments and girls’ marijuana and alcohol use and violence. Findings extend the generational thesis of drug eras and counter suppositions that rejection of crack might enhance future prospects. Interrupting intergenerational transmission of drug-related problems requires mother–daughter bonds be addressed.