"The Mole, the Mob, and the Meatball"Chuckles first appears during the Toy Mafia episode as one of its high-ranking members and the one that new recruits must speak to in order to enter its organization. Sam and Max, wanting to get within the Toy Mafia to stop it from the inside, address Chuckles to gain membership. Thus, he tasks them with the three recruitment duties of killing their associate Sybil, planting one of the hypno-bears in Bosco's shop, and retrieving the mafia's beloved meatball sandwich, warning them that he has surveillance all over town and will kill them both if they try anything.
The duo manage to meet these tasks through tricking Chuckles into believing they killed Sybil (really only shooting a coffee cup full of ketchup in front of her). Once their cover is blown, Sam and Max shake off the Toy Mafiosos sent after them although Chuckles seemingly disappears from the story entirely. Once Ted E. Bear/Harry Moleman is defeated and the toy factory producing the hypno-bears is destroyed, Chuckles reappears, telling an unknown informant that their plan is in motion.
"Abe Lincoln Must Die!"
Shedding his Toy Mafia getup, Chuckles appears once more with his true job being revealed as a Secret Service agent. His plan is also revealed: to use the American government in order to hypnotize the masses on behalf of Hugh Bliss. After Max destroys the fake President installed in the Oval Office, Chuckles falls back on the plan to bring the Abraham Lincoln Memorial to life via robotics, intending to use Lincoln's iconic status to appeal to those voting in the next election. Chuckles sits atop the giant Lincoln's shoulder, possibly operating the machine or at least overseeing it all.
Determined to stop Chuckles' plot, Sam has Max run for President as Lincoln's opponent and muck up his approval ratings by well-timed cue cards to make his statements sound crude and un-American and by staging it as though he coldly rejects Sybil. Enraged, Lincoln charges into a full-blown rage to destroy everything in sight. Both Lincoln and Chuckles are stopped by Sam and Max planting a tracking device on the statue/machine and then attacking it with one of the US government's missiles. Lincoln is reduced to his head and Chuckles is found dead among the wreckage.