Though Moore continued playing on the road—as he would for over 40 years—he began competing and placing in top-tier tournaments. His tournament career was to be overshadowed by an enduring series of runner-up finishes that would earn him the nickname "pool's underpaid prince" in such publications as Esquire Magazine. The name that stuck with him for life, however, was Cowboy. According to Moore, he became 'Cowboy' Jimmy Moore when he appeared at the Commodore Hotel championships in New York City in the 1950s wearing the required tuxedo, but nevertheless sporting cowboy boots and his signature white Stetson hat.