Tom Cunningham played guitar, fiddle, and mandolin as band leader for KSON's Flatbed Band in the 1980s, and later served as host and emcee for Sea World's Dolphin Show for several years, doing an estimated 3000+ shows. Cunningham has played locally at the San Diego Zoo, the Lyceum Theater, Wild Animal Park (now Safari Park), the Star of India, the Hotel Del Coronado, Loews Coronado Resort, the Del Mar Fair, Legoland, and the San Diego Convention Center.

Cunningham has also worked with Las Vegas productions including Superstars Live in Concert, Hot August Nights, and Adventures in Parrotdise. Locally, his Americana/bluegrass group the Tom Cunningham Band plays regularly at casinos, private parties, corporate events, and festivals.