Canboulay Productions was registered in 1991. The business was founded with partners Rawle Gibbons, Michael Phillips, Margaret Walcott and Kenwyn Crichlow, on the basis of Rawle Gibbons’ trilogy of calypso dramas. ‘Sing De Chorus’ (1991), ‘Ah Wanna Fall’ (1992) and ‘Ten to One’ (1993), were performed during the Carnival season annually. For Carnival 1994, Canboulay commissioned ‘The Roaring Seventies’ from playwright Zeno ‘Obi’ Constance. Over the next 2 years we devised work from scenarios scripted by Gibbons to fill our seasonal performances. ‘Ay Ya Yai’ (1995) and ‘Juba Dubai’ (1996) completed Canboulay’s initial phase as a producer of entertainment for the Carnival season. In 1999 we began our publication enterprise. Along with Jamaican publisher Ian Randle, we made available A Calypso Trilogy (1999), including recordings of the music by Sanch.

Our publication history expanded in 2005 with Michael Phillips’ initiative to score steelband Panorama music. Our music score repertoire grew from Panorama arrangements to steelband scores for various occasions and specific instruments. On the basis of this undertaking, Canboulay was also responsible for the publication of scores for the Graded Steelpan Exams administered by the University of the West Indies.

In 2014 Canboulay embarked of a fund-raising campaign for the benefit of an ailing King of Calypso, Mighty Sparrow. ‘If Sparrow Say So’ took the form of a series of lecture-performances around the country to meet our donation target of $100,000, which was achieved. In 2016 we undertook another fund-raising campaign to engage a younger generation with the music of Black Stalin in a school-based competition. Entitled ‘Sing for the Man’, this project allowed students to showcase their talent in various art disciplines and, more than money, demonstrate their understanding and deep appreciation of the singer’s work. Since 2017, Canboulay Productions has collaborated with Tout Moun Productions to mount Theatre-in-education performances for secondary school children. Productions include: Julius Caesar, Ti Jean and The Tempest. In 2018, Canboulay Productions in association with the Lloyd Best Institute, staged 'Sing De Chorus' for Calypso History Month. 'Sing De Chorus' was performed in February 2019 for carnival, this time in association with Normandie Hotel. For Calypso History Month 2019, we produced ‘Ah Wanna Fall’ in association with Newtown Playboys and i95.5fm.

Due to the COVID pandemic, Canboulay Productions collaborated with the local radio station i95.5fm to host a weekly radio calypso tent entitled ‘Calypso on the Frontline’. Canboulay Productions participated in honouring the prolific author Sam Selvon at the Bocas Lit Festival with a short performance of ‘Ways of Sunlight’ (2023).