Chucktown refers to Charleston, South Carolina. Also known as The Chuck, Charlie-o, Chucktezzy, ect. Originally named Charles Town after King Charles, hence "Chuck"town. Not the West Virginian city of Charleston. Chucktown was also featured as a question on an episode of discovery channels Cash Cab, just for you West Virginians out there who disagree.
A person who is genuinely hilarious in the way they look and or act. Only people who are EXTREMELY hilarious to watch can be classified as this, and only a few true chucklemonsters have been spotted.
You: "You see that retarded girl scribble on her window and then nod in approval? That was hilarious!."
Another, more amusing word for comedian. Comes from the words chuckle (to laugh) and -monger (a suffix denoting dealership), hence, chucklemonger, a person who deals in and sells chuckles.