With his brothers he formed the Pickett Brothers Bronco Busters and Rough Riders Association, performing throughout the west. In 1905 he joined the 101Wild West Shows based at the 101 Ranch near Ponca City, Oklahoma, becoming friends with another Oklahoma legend, Will Rogers.
Pickett became a favorite on the rodeo circuit although Jim Crow laws kept him from performing in many places, including Madison Square Garden. He appeared in early western movies, often with friend Tom Mix.
In 1972 he became the first African American member of the National Rodeo Hall of Fame in Oklahoma City and in 1989 was inducted into the Pro Rodeo Hall of Fame and Museum of the American Cowboy in Colorado Springs.