Squiggy was one of the main characters in the sitcom "Laverne & Shirley". He appeared on a reality TV show with the Simpsons. He entered the house to help increase ratings, but fails to do so. He was apparently "killed", when the house was destroyed after falling down a waterfall.
Behind the Laughter
"Squiggy" being sent to boost The 1895 Challenge ratings is another reference to The Cosby Show, whom sent "Smitty" (Adam Sandler) to the Cosby's house.