Press Your Luck is an American television daytime game show that originally ran on CBS from 1983 until 1986. The show was known for the "Whammy", a red cartoon creature with a high-pitched voice. Landing on any Whammy space reset the contestant's cash balance to zero, accompanied by an animation that showed the Whammy taking the loot, often with amusing results in the process.
At the reading of Marguerite Pewterschmidt's will in "Peter, Peter, Caviar Eater", Peter says "big money, big money, no whammies, no whammies, STOP!," a reference to the game show Press Your Luck.
Seamus decides to "press his luck" and ask Meg out on a date in "Follow the Money", but the game board ends up handing him a Whammy.