The lyrics to Chinese Checkers were written by PI's vocalist Sara Geller, inspired by a trip she took to see her grandparents. The funky music was composed by Christopher Malone. At the time of its recording, it was one of the few songs where PI breaks away from their all-acoustic instrumentation and incorporates funky electric guitar. Christopher enjoyed playing the 70's Rhodes keyboard (with his left hand) the clavinet (with his right) to give this song its fun, funky feel. Everyone in the band at the time of its recording is called out for individual solos. The song starts with a psychedelic, dreamy intro and ends rhythmically the same way.