for two and a half years, cunliffe taught music at central state university in wilberforce, ohio. he then toured as pianist and arranger with the buddy rich big band, and worked with major recording artists including frank sinatra. he returned to southern ohio for a few years, where he was the "house pianist" at the greenwich tavern in cincinnati, playing with woody shaw, joe henderson, freddie hubbard, benny golson and james moody. in 1989 he moved to los angeles, and shortly after that won the 1989 thelonious monk jazz piano competition, which was judged by pianists hal galper, ahmad jamal, and barry harris. cunliffe worked occasionally with buell neidlinger's group "thelonious," and in 1990 joined the clayton hamilton jazz orchestra, and the clayton brothers quartet, recording a number of albums with them on the qwest, capri, and fable labels. he also worked in duo with the jazz flutist holly hofmann, touring with her extensively, and recording on the capri and azica labels with her, notably, the session "live at birdland," with the great bassist ray brown.