Larry Pops Up! was a 1995 non-productivity program created released for free in promotion of Leisure Suit Larry: Love for Sail!. There were a few free expansion packs released that gave Larry more comments.
Larry pops up on the screen from time to time to give jokes, advice, and other pointless remarks, as well as any wav files you add for him to play.
It is a tiny program written by Don Munsil (who also helped design LSL7: Love for Sail!) to play random WAVe files after a user-defined period of inactivity (i.e., if the user doesn't type or move their mouse for 10 minutes, it pipes up!). It will play any and all WAV files that are placed in its directory. It even comes with a few Larry lines to get you started.