He is an eight-time winner of Trinidad's Calypso Monarch competition, most recently in 2009. Chalkdust's winning song performances for these most acclaimed Calypso Crowns are: 1976 ("Three Blind Mice" and "Ah Put on Meh Guns Again"); 1977 ("Juba Dubai" and Shango Vision"); 1981 ("Ah Can't Make" and "My Kind of Worry"); 1989 ("Chauffeur Wanted" and "Carnival Is the Answer"); 1993 ("Kaiso Sick in de Hospital" and "Misconceptions"); 2004 ("Fish Monger" and "Trinidad in the Cemetery"); 2005 ("I in Town Too Long" and "Ah Doh Rhyme"); lastly in 2009 (Doh Touch My Heart). Before only the Mighty Sparrow had more wins in that competition, until 2009 when Chalkdust also achieved eight wins in the Calypso Monarch. Chalkdust also won Carifesta in 1976, the World Calypso King title in St. Thomas, US Virgin Islands eight times, and the Calypso King of the World in New York City on the two occasions when that competition was held.
Chalkdust, who holds a Ph.D. in history and ethnomusicology from the University of Michigan, is an Assistant Professor of History at the University of the Virgin Islands, and frequently lectures and offers workshops on the history and culture of calypso music. He is the author of the books Rituals of Power and Rebellion: The Carnival Tradition in Trinidad and Tobago and From the Horse’s Mouth, a socio-cultural history of calypso from 1900 to 2003.