Reg Kesler began his rodeo career at the age of 14 at the Raymond Stampede, competing in the boys steer riding. At the time, it was common for cowboys to compete in many or even all the rodeo events, and Kesler was no exception as he grew into his rodeo career. He participated in all five major rodeo events of the time: saddle bronc riding, bareback riding, bull riding, tie-down roping and steer decorating, a precursor to steer wrestling. Kesler especially excelled in the roughstock events, namely saddle bronc riding and bareback riding, appearing in the top four in the Canadian standings in those events six times. He was also a successful competitor in the wild cow milking and wild horse racing, an outrider in the chuckwagon racing, and a well-known pick-up man. Kesler was a ProRodeo Hall of Fame and Canadian Pro Rodeo Hall of Fame inductee.