Not all of the income for the Johnsons derived from bootlegging, however. Johnson worked the family farm with his brothers, and was plowing a field behind a mule one day in the late 1940s when his brother L.P. asked him to pilot his car at a race at North Wilkesboro Speedway. Believing a car race would be more fun than plowing a field, Johnson consented. He eventually placed second, casting the die for a long, distinguished career as NASCAR's bad boy, often adapting such tricks as the bootleg turn on corners of oval tracks.
In 1953, Johnson entered his first NASCAR race at the 1953 Southern 500 held in Darlington. He began to establish speed records and local race tracks until his arrest in 1956. Upon his release from prison, he proceeded to make his mark as one of NASCAR's most innovative and intimidating drivers. The world of stock car racing had changed significantly in the late 1950s; changes that included paved tracks, the organization of NASCAR, and the participation of marketing and gear heads from Detroit's Big Three automakers.