[citation needed] Hickman was born in Winston-Salem, North Carolina and was known as a "truck-stop" comedian, which denotes a genre of comedy that was meant to appeal to a Southern grass roots demographic and whose material was marketed mainly through truck stops.
He started his career at the young age of 15 when he won a North Carolina state talent show, sponsored by the Women's Club of America.
Hickman also appeared on HBO, Showtime, and The Playboy Channel; performed on the Hee Haw television show; opened shows for comedians Jackie Gleason and Sammy Davis Jr.; and opened concerts for musical artists Tom Jones, Liza Minnelli, Tanya Tucker, Aretha Franklin, Mel Torme, Anita Baker, Lee Greenwood and George Jones.
Despite his lack of widespread notoriety, his cult following continues on due to the commitment of Laughing Hyena Records to honor Hickman's last request, for them and only them to continue marketing his CDs for future generations to hear per the testimony of his best friend and company founder, Arnie Hoffman, as found on the inner sleeves of Hickman's CDs.
Jay was married to Julie Hickman, who regularly attended his standup comedy performances at the Cheetah III, a strip joint in Fort Lauderdale, Florida in 1979.