Waylon Jennings Belt Buckle W/COA - Waylon Jennings personally owned and worn square?Million Dollar Cowboy? Jackson Hole, Wyoming belt buckle. The ?Million Dollar Cowboy? Bar was the venerable honkytonk founded in 1937. During the 1970s, the venue hosted legends like Waylon Jennings who performed ther, as well as Willie Nelson, Glen Campbell and others. Artists of such caliber as Jennings played there because of the ?cool factor.? The Million Dollar Cowboy Bar was purchased by the Silver Dollar Inc (SDI) in 2018. The Outlaw country man Jennings was rarely seen not wearing a belt buckle with his attire as they became standard additions to his jeans, cowboy boots and cowboy hat. Waylon Jennings remains one of the most significant forces in country music. The belt buckle is accompanied by a COA signed by Jimmy Velvet.