Leon Pettiway was born on August 15, 1946, and grew up in racially segregated Durham, North Carolina. He started his academic career at North Carolina College at Durham (now North Carolina Central University) under Dr. Theodore Speigner, one of the few African Americans in the nation with a doctorate in geography at that time. Pettiway obtained his master's in sociology from the University of Chicago in 1976. Continuing his interest in geography, he attended the University of Wisconsin-Madison and received his Ph.D. in 1979. Pettiway was an Assistant Professor at Temple University from 1980-1985 and Associate Professor at the University of Delaware from 1985-1994. He became an Associate Professor of Criminal Justice at Indiana University in 1994. While at IU, Pettiway taught courses on urban crime patterns, drug use and criminal behavior, theories of crime and deviance, and quantitative methods. He remained at IU until his retirement in 2012 with the title Professor Emeritus of Criminal Justice.

Pettiway contributed numerous studies to the field of criminology. In his initial research, Pettiway focused primarily on the felony of arson and progressed into the study of urban lifestyle, specifically of drug-using criminal offenders. In 1989, Pettiway was awarded a National Institute on Drug Abuse (NIDA) grant to study drug use and the spatial patterns of crime. In his research, he employed the assistance of former offenders and recovered drug users to conduct interviews of active drug users and offenders in North Philadelphia. The research resulted into a series of publications: "Participation in Crime Partnerships by Female Drug Users: The Effects of Domestic Arrangements, Drug Use, and Criminal Involvement" (1987), "The Drug and Criminal Activities Patterns of Urban Offenders: A Markov Chain Analysis" (1994), and "Copping Crack: The Travel Behavior of Crack Users" (1995). Pettiway also published two books based on the life-history interviews recorded during the time he was in Philadelphia: Honey, Honey, Miss Thang: Being Black, Gay, and on the Streets (1996) and Workin' It: Women Living through Drugs and Crimes (1997). The books helped Pettiway gain national recognition for being one of the first to observe how race, class, and gender intersect and influence the criminal behavior of urban individuals.

Pettiway's later life and work have been inspired by his conversion to Buddhism and his position as a fully ordained Tibetan Buddhist monk.