Henry Shepherd was born and raised on a plantation in Tallulah, Louisiana, where the primary crops were peanuts and corn. When he moved to Las Vegas, Nevada in 1967, he worked as a bartender at the Sands Hotel. Shepherd was able to send his daughter to college because he was working for the Culinary Workers Union Local 226. Leaving the Sands Hotel, he went to the Landmark Hotel and Casino, and then went to Circus Circus Hotel. The Luxor Hotel and Casino was his final stop in a bartending career that spanned over three decades.