Since its inception, the Living Legacy Jazz Award has been given to twenty-five distinguished artists.  Additionally, a special Millennium Award was conferred on Dr. Billy Taylor in 2000. Mid Atlantic Arts did not bestow an award in 2020 due to the COVID-19 Pandemic.

2019: Charles Tolliver
2018: Toshiko Akiyoshi
2017: Odean Pope
2016: Ron Carter
2015: Gary Bartz

2014: Joanne Brackeen
2013: Nathan Davis
2012: Muhal Richard Abrams
2011: Phil Woods
2010: Roy Haynes
2009: Frank Foster
2008: Kenny Barron
2007: Benny Golson
2006: Oliver Lake
2005: Rufus Reid
2004: Randy Weston
2003: Keter Betts
2002: Jimmy Heath
2001: Joe Kennedy, Jr.
2000: Shirley Scott
1999: Reggie Workman
1998: Dr. Donald T. Byrd
1997: Larry Ridley
1996: Barry Harris
1995: Robert “Boysie” Lowery
1994: Clark Terry
Special Millennium Award given to Dr. Billy Taylor