I don't repeat too many songs, as I'm into discovering new music most of the time.
There is a set of songs that I DO play fairly often to evaluate new equipment or cables, and that is tracks 3-6 from "The Wall" - Another Brick in the Wall, Pt. 1, The Happiest days of Our Lives, Another Brick in the Wall, Pt. 2 and Mother.
p.s. Caught in the Act is one of my favorite live albums of all time, and was on heavy repeat around here during the 70's and 80's.