Canutt won the saddle-bronc competition at the Pendleton Round-Up in 1917, 1919, and 1923 and came second in 1915 and 1929. He won the steer bulldogging in 1920 and 1921, and won the All-Around Police Gazette belt in 1917, 1919, 1920 and 1923. While in Hollywood in 1923 for an awards ceremony, he was offered eight western action pictures for producer Ben Wilson at Burwillow Studios; the first was to be "Riding Mad". He won the first leg of the Roosevelt Trophy. The trophy was awarded to the cowboy who accumulated the most points between Cheyenne Frontier Days and the Pendleton Round-Up. After he won three years in a row at the Fort Worth Rodeo in Fort Worth, Texas, it came to be known as "Yak's show."