A fifth-generation Japanese-American, Shimabukuro initially gained attention in Hawaii in 1998 as a member of Pure Heart, a trio with Lopaka Colón (percussion) and Jon Yamasato (guitar/vocals). Shimabukuro was working at a music store in Honolulu when the group released its eponymous first album, which won them four Na Hoku Hanohano Awards (the Hawaiian counterpart of the Grammy Awards) from the Hawaii Academy of Recording Arts: Island Contemporary Album of the Year, Most Promising Artist(s), Album of the Year, and Favorite Entertainment of the Year, the latter determined by unrestricted public vote. The album, "Pure Heart", was also named one of the Top 50 Hawaiian albums of all time by "Honolulu Magazine".