He started selling pennants at games in 1962 and quickly endeared himself to the Cowboys fans with his western outfits, magic tricks, trademark whistle, and galloping along with a hobby horse. Crazy Ray has a place in the fans' wing of the Pro Football Hall of Fame.
He never officially worked for the Dallas Cowboys Organization, but was given a Special Parking Pass and All-access for home games. He was also known as the "Whistling Vendor" at Dallas Tornado soccer games and Texas Rangers baseball games. He was also known to be present at the State Fair of Texas and various concerts entertaining the public.
Crazy Ray was also had a special friendship with rival Zema Williams, the Washington Redskins' unofficial mascot. In some photographed pictures, Crazy Ray and Mr. Williams are seen pretending to fight with each other during games.