Wicked Willie The Boardgame (1994)

Adult boardgame based on the comic Man's Best Friend by Gray Jolliffe. Player move up and down a track, advancing by answering questions, with words starting with a letter decided by a drawn card. Acceptable answer lets you advance 1-3 spaces. getting to the end of the track gives you one hat (that looks like a condom). First player to get three hats win.