He won the Roosevelt Trophy the first time in 1925 by competing in two rodeos and winning the all-around events at both Cheyenne Frontier Days and the Pendleton Round-Up.
At Madison Square Garden, he won the calf roping title three times.
[3] Crosby wore an old black hat that represented good luck, which fans came to recognize and use as a cue to cheer.
He remarked, "Someday, to their surprise, I'm going to wear my Sunday hat and see if it's the old black felt or the man they're always cheering".
[4] Crosby was inducted into the Pendleton Round-Up and Happy Canyon Hall of Fame[5] in 1974.
Crosby was inducted into the Rodeo Hall of Fame of the National Cowboy and Western Heritage Museum in 1966.