Born into a musical family (father Mick a Jazz pianist and sister Sally a clarinet teacher), Gillespie was first inspired to write songs after hearing Leonard Cohen’s “You Know Who I Am” on a local radio show at the age of 14. Some years later Gillespie makes his professional debut busking in Paris subways, playing to audiences in London folk clubs and Sydney’s Darlinghurst cafes before returning to Auckland in the early 80’s.
Wayne quickly became one of the leading figures in the prominant Auckland Acoustics movement playing pubs, cafes and folk clubs augmented by his band of brilliant musicians, Denny Stanway (vocals), Brendan Power (Harmonica) and Bob Shepheard (Fretless Bass).
Wayne's first album, ‘Wayward Son’ was released on Gillespie’s own independent label in June 1984. The album was acclaimed by the NZ rock press and made the finals of the New Zealand Music awards in the Most Promising Vocalist & Folk Album of the Year categories. The song ‘Away With You’ also won an APRA NZ Songwriting Special Award in the same year.
In 1985 he contributed two tracks to the Auckland Acoustics Album (also featuring local acts such as Mahinarangi Tocker, Kaith Tait, Acoustic Confusion and Chris & Lynne Thompson). Later in the year Gillespie shared production duties with Chris Knox on songwriter Nick Smith’s debut EP ‘Flanker’ released by Real Groovy Records