In Ultima VI, Chuckles gave the Avatar Lord British's stupid nickname: "Mr. Nose," which annoyed the king to no end. He also sent the Avatar on a wild goose chase to collect clues throughout Britannia, only to learn some useless advice from Smith the Horse. Chuckles was vital in Ultima VII, because after playing and winning his game of single syllable, the Avatar received a hint: the hero had to get the fortune told by the gypsies in Minoc. At this time, Lord British already had become quite annoyed with Chuckles.
Chuckles wasn't in the castle in Ultima Underworld II when it was imprisoned, but Dupre mentioned him. He said jokingly that they should be glad to be imprisoned, because the people outside had to endure Chuckles. He wasn't seen in Ultima IX, which was curious, and people suspected that a giant rat ate him.
In Ultima V, there is a curious matter involving Chuckles, a prison inmate named Drudgeworth, and a dead body hidden in a room behind the fireplace in Chuckles' room. Although Drudgeworth claims it is Chuckles' fault he is locked up, Chuckles appears to feign ignorance of the whole affair, saying nothing of the corpse, and responding "Who?" when asked about Drudgeworth.