One of calypso's true intellectuals, Chalkdust (born: Hollis Urban Lester Liverpool) is known for his hard-hitting, politically tinged lyrics. The record holder for most years as a National Calypso Monarch finalist, he won the prestigious competition in 1976, 1977, and 1981. Chalkdust began writing songs as a student at St. Mary's College in 1954, composing songs for the school football team's intercollegiate matches.

He returned to teach at the school after graduating from the University of the West Indies, with a bachelor's degree in history and sociology, in 1973. When word reached the school administrators that he was continuing to perform, Chalkdust's position was terminated. The aftermath of the school's decision created a media-fueled controversy. Calypso star Lord Protector publicly supported him, while he answered his accusers with the powerful tune "Reply to the Ministry." The reaction of Chalkdust's many fans led to the school reinstating him. Chalkdust has continued to balance his musical career with academic pursuits.

He earned a master's degree in history and African history and a Ph.D. from the University of Michigan in history and ethnomusicology. A visiting assistant professor of history on the St. Thomas campus of the University of the West Indies, Chalkdust published his first book, Rituals of Power and Rebellion: The Carnival Tradition in Trinidad and Tobago, in April 2000. ~ Craig Harris, All Music Guide