He was a famous singer during the 1930s and Pappy used to listen to his music, implying that he and Chip must have the same age. He is the patriarch of the famous Skylark family along with his wife. In the cartoon 1930's version of Dimmsdale, Chippington has a band of anthropomorphic animals that play instruments (other animals) called Chippington Skylark and the Noah's Arkestra.
Pappy was telling his grandson, Timmy Turner, about Chippington when Timmy tried to show Pappy his Chip Skylark CD. Pappy corrected Timmy and said that CD was for "Chip Skylark III" and said that he preferred the real Chip Skylark, who was Chippington, a singer from his hey-day. Later, when Timmy wished Dimmsdale into a 1930's cartoon, twenty bucks made Timmy and his grandfather rich enough to attend a Chippington Skylark performance at a bar. Chippington took the stage with his animal band and sung the song Icky Vicky in a 1930's fashion.