This intimate portrait of modern jazz pianist, Barry Harris, becomes a historic walk with some of the best-known jazz musicians of the 1950's and 60's. Memorable scenes span from archival footage of Harris playing at his piano to more recent reminiscing about his circle of friends and influences, such as Charlie Parker, Thelonius Monk, Dizzy Gillespie, and Miles Davis. Dubbed the "key conservator" of bebop music by Gary Giddins, Jazz Critic for The Village Voice, Harris shares with us his heartfelt music, insights into his personal style of playing, and his far-reaching love of teaching. Checkerboard has created a lively picture of a musician and teacher, who has worked hard, often in the face of prevailing musical trends, to keep the spirit of bebop alive. Through his playing, composing, band leading, and teaching, Harris has touched the lives of many. During the film, we see Harris on many levels. In one scene, his playfulness surfaces as he composes a new work. During a gig at the Village Vangaurd in New York City, he banters with the small audience and plays soulfully with his trio. Later in the film, we see him tackling an orchestral choral work at a concert. Highlights include many of Harris' students, of all ages and nationalities, sharing stories about this beloved musician as a teacher and mentor. Harris retains his unflappable good humor throughout this documentary on one of the world's living legends of jazz.