[5] Cunliffe described himself as having been drawn to "anything with hip harmony in it" with great melodies, and he loved listening to The 5th Dimension, Burt Bacharach, and Herb Alpert.

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.

He also worked in duo with jazz flutist Holly Hofmann, touring and recording on the Capri and Azica labels with her, notably, the session "Live at Birdland," with the great bassist Ray Brown.

In 2000, he recorded a sextet session of Earl Zindars' music, and in 2001 Cunliffe documented his working trio of ten years with Live at Bernies, which was released on both CD and vinyl.

Cunliffe has been a member of LaBarbera's quintet featuring saxophonist Bob Sheppard and trumpeter Clay Jenkins virtually since its formation in the early 1990s.

He accompanied pianist Marian Petrescu in selections from the Resonance Jazz Orchestra Plays Tribute to Oscar Peterson CD.

Cunliffe's concerto for trumpet and orchestra entitled fourth stream... La Banda (2010) was nominated for a Grammy in that year,[citation needed] and was premiered by Terell Stafford and the Temple University Symphony Orchestra, conducted by Luis Biava, at Verizon Hall in Philadelphia, and at Alice Tully Hall in New York City.

Cunliffe's Symphony #1, Hearts Reaching Upward premiered in 2013 by trumpeter Kye Palmer, and the Cal State Fullerton Wind Ensemble.

Cunliffe won the 2010 Grammy Award for Best Instrumental Arrangement of Oscar Peterson's "West Side Story Medley".