Dapper Denver Dooley first appeared in the cartoon "Square Shootin' Square" in 1955. Dooley returns in 1957 to 1959 cartoons "Box Car Bandit, "Dopey Dick the Pink Whale", "Misguided Missile", "Half Empty Saddles", "Jittery Jester", "Yukon Have It" (Chilly Willy cartoon), "Panhandle Scandal and "The Tee Bird". In these short films Dooley had more or less replaced Wally Walrus and Buzz Buzzard as Woody's primary foil. He, in turn would later be replaced in the role by Gabby Gator and Ms. Meany.
One of his traits was when he was defeated, which was often, the emotional Dooley would begin to cry.
Dapper Denver Dooley reappears in the TV Series The New Woody Woodpecker Show in 5 episodes total throughout seasons 1 and 2 "Cheap Seats Woody", "Lap It Up", "Spa Spa Blacksheep", "Difficult Delivery" and "Out of Line" (marks the last appearance of Dapper Denver Dooley). In that series, he is voiced by Jim Cummings, and His Grungy Appearance is replaced with a Cleaner and Male version of Miss Meany.