Ray Holman began playing steel drums professionally at 13, with Ellie Mannette's Invaders. He developed skill under the informal tutelage of the legendary pan tuner, though they had little training in theory. As a teenager, he became known as a virtuoso solo player, becoming the youngest person ever to win the solo division of the "ping pong" (an early name for the tenor pan) competition in 1960 (Liam Teague has just recently broken this record). He traveled from group to group for a time, joining Starlift, Destination Tokyo, Pandemonium, Exodus, the Hummingbirds, and Phase II Pan Groove. During this time, he gained a reputation as one of the five major steel band arrangers (with Len "Boogsie" Sharp, among others), as he repeatedly led groups to victory in the Trinidadian national Panorama competitions, with arrangements for bands numbering in the neighborhood of 120 performers. He also gained a reputation for challenging the system to some degree by departing from the traditional Calypso tunes for the competitions and writing his own original tunes. He also occasionally made arrangements from European classical music, much to the surprise of steel band traditionalists. As a result, he has become one of the most respected and sought after musicians in the steel band form, both as a solo player and as an arranger. In 1993, he was awarded the Hummingbird Silver Medal of Merit by the government of Trinidad and Tobago for his contributions to the culture of the nation.