As a filmmaker from Memphis, Leonard has specialized in documentary subjects about the rich music heritage of the American South. His first film as director: Why Elvis? (PBS) explored the phenomena following the biggest Memphis musician of all. Respect Yourself: the Stax Records Story (PBS' Great Performances), and Johnny Cash's America (A&E Biography) are among many projects Leonard has served as cinematographer for with acclaimed directors Robert Gordon & Morgan Neville.  Leonard & Gordon partnered to produce & direct a series of twenty-five short films for the Mississippi Blues & Country Trail projects. With Gordon & author Peter Guralnick, he filmed the bonus material to accompany a complete series of Guralnick's works made into E-books. As editor & producer of Big Star: Live in Memphis, Leonard assembled a box of tapes that had remained unedited for eighteen years to finish the only complete professionally filmed concert from Alex Chilton's long career.

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As an art photographer, Leonard has been greatly inspired by his friend & fellow Memphian William Eggleston (also a longtime friend of Chilton). His work has been exhibited in galleries & museums & in 2016 German publisher Kehrer Verlag published Tender is the Light, a book of Leonard's work.

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Leonard was involved in the Memphis music scene from an early age. He was disc jockey for many years with community radio station WEVL-FM where he also became station manager at age nineteen when the fledgling station still operated with only ten watts (he once broadcast a Pantherburns performance from the studio using one microphone). He was founding president of Save Our Shell, Inc. a group that preserved and operated the historic Overton Park Shell (the 1936 amphitheater where Elvis Presley and Johnny Cash both made their first professional appearances). Leonard organized many concerts there including memorable performances by Alex Chilton.