An active performer of jazz and classical piano music, Luke Gillespie is the recipient of numerous awards, including best performance from the Indianapolis Star in 1993, the 1990 Copland Piano Concerto Competition at Indiana University, and the 1994 Indianapolis Jazz Festival Competition.

He has recorded with the Arts Center Jazz Collective, David Baker, Bruce Bransby, Buselli-Wallarab Jazz Orchestra, James Campbell, Steve Davis (drums), Everett Greene, Sylvia McNair, Dan Perantoni, Eugene Rousseau, Dominic Spera, Wanda Stafford, and Tom Walsh (with whom he toured Europe in May 2002-03, Japan in May 2004-05, and China in May 2009).

He has performed with Jamey Aebersold, Eric Alexander, Ron Blake, Benny Golson, Wycliffe Gordon, Bunky Green, Jimmy Heath, Steve Houghton, Ingrid Jensen, Kelley Johnson, Pat LaBarbera, David Liebman, James Moody, Ed Neumeister, Chris Potter, Rufus Reid, Arturo Sandoval, Jim Snidero, Rodney Whitaker, the Smithsonian Jazz Masterworks Orchestra and Pablo Ziegler.

Gillespie is included in Jazz Play-Along, Vol. 76, "How to Learn Tunes," by David Baker (Aebersold). He has published articles on the aesthetics of jazz and classical music as well as a book, Stylistic II/V7/I Voicings for Keyboardists (Aebersold, 2000, second printing, 2006), endorsed by Danilo Perez, Geoff Keezer, David Liebman, David Baker, and Frank Mantooth. His solo jazz piano CD, Footprints, was released on RIAX records (2003), and he has released two trio CDs, Live at the Station (2010) and the new Third Base Line (2011), both on Watercourse records.