He specialized in jokes about Doctor Robotnik, the idea being that the best way to deal with a bully is to make fun of him. However, Robotnik tricked Willie into taking a flight on an aircraft and stranded him in the Scorchio Zone desert. Willie decided to give up comedy. When Tails arrived to carry him out of the desert, they were attacked by an advanced Sandworm Badnik. Willie distracted the Badnik by telling it a joke, giving Tails a chance to destroy it. Willie realized that he couldn't give up telling jokes, and resumed his gig at the Comedy Club back home.
When the bank robber Claws escaped from prison and headed into the Polarzone, Tails recruited Willie Waddle to help him. After Claws believed that Tails had been defeated for good, tied up on a melting ice floe, Claws revealed where he had hidden the cash he'd stolen. After this, Willie freed Tails underwater, allowing the fox to surface and take Claws down. Willie bombarded Claws with cold-themed puns until Claws was taken away by the police.