Leonard “Lenny” Ross

His given name was Leonardo del Rossi, born near 6th and Fitzwater Streets in Philadelphia with several siblings. He dropped out of school after the sixth grade but he did learn to play the guitar, and he could sing and dance and began performing on street corners.

Catherine Carmichael became his wife around 1926 and their daughter Alverda was born in 1927. Lenny appeared in amateur shows which led to appearing in local theaters and nightclubs. They lived with her family during the Great Depression. To put food on the table, Lenny worked as a chauffeur for a private family, but used what bookings he could get to polish his act. 

About the time Lenny Jr. was born, around 1937, Lenny was becoming known as the “dirty-mouthed comic.” The story was that teenage Lenny told crude jokes on street corners and was so funny that members of the mob “asked” him at gunpoint to repeat his performance, so he knew he was on to something. 

Getting away with that material in a mixed audience, however, was pushing the envelope. But Lenny thrived on the controversy so he kept doing it. It’s easier to gain fame and fortune by being bad than by being good. On the 1940 census his occupation was recorded as nightclub master of ceremonies.  

Throughout World War II he found a steadier income in front of what seemed to be a more morally lax crowd at Atlantic City. It was also a seasonal crowd, so he’d return to shock his audiences in Philadelphia on occasion. There in 1947 he was sentenced to six months in Moyamensing Prison for “lewd performances” and “debauching the morals of citizens.” 

The next year he came once again to Atlantic City. This time public figures weighed in on the decency of his material and if it could even be considered “entertainment.” 

The Ross family was still listed on Philadelphia census records in 1950 but Lenny spent much of his time in Miami and Chicago. It would be more than 20 years before he performed again in Philadelphia. 

By then the post-war 50s and turbulent 60s had irreversibly impacted the moral climate, helped along by establishing ratings for motion pictures. What was once indecent wasn’t so much anymore, and X-rated humor had its own established and therefore accepted category. Lenny was considered the comedian who was ahead of his time. Some old-timers in the nightclub business even threw an appreciation dinner for him in 1975. 

It was his health, however, that finally put an end to his brash performances. Lenny Ross, who inspired others in later years like Lenny Bruce to be crude and lewd, died of cancer the following year. His wife was buried beside him five years later.