In Montserrat, Keithroy “De Bear” Morson will be the first artist to be honored by the Legends of Montserrat Cultural Excellence Awards, a new initiative dedicated to individuals who help preserve the island’s culture. A leading figure in calypso, the singer is also recognized for his commitment to passing on traditional masquerades to younger generations.
Announced on November 9, 2026, this award recognizes a career spanning several decades. The first ceremony will be held on December 6 at the Montserrat Cultural Centre.
A New Award for Montserrat's Cultural Figures
The Legends of Montserrat Cultural Excellence Awards were launched by the Office of the Premier, under the auspices of the Montserrat Arts Council. The goal is to recognize the contributions of artists, educators, and cultural figures who have shaped Montserrat’s identity. The program covers several disciplines, including music, calypso, masquerades, dance, literature, and the performing arts. It also aims to document the life stories of these individuals in order to pass on their legacy to future generations.
Under the theme “Celebrating Our Culture. Supporting Our Icons,” this initiative aims to honor artists during their lifetimes. The Montserratian diaspora will be invited to participate in the celebrations, particularly through testimonials and tributes. For this first edition, the choice fell on De Bear, whose contribution extends far beyond music competitions.
De Bear: A Career Spanning Montserrat and Antigua and Barbuda
A native of Montserrat, Keithroy Morson was introduced to music as a child through a string band, a traditional ensemble that primarily uses stringed instruments. He began competing in junior calypso competitions in 1985, before moving on to senior competitions two years later. His career unfolded between Montserrat and Antigua and Barbuda, where he won several titles. He gradually established himself as one of the most respected competitors in the Leeward Islands.
His regional achievements include five titles at the Leeward Islands Calypso Monarch competition, won in 2007, 2012, 2015, 2023, and 2026. He won his first three titles representing Antigua and Barbuda, followed by his victories in 2023 and 2026 representing Montserrat. In August 2026, De Bear claimed his fifth title in Anguilla with the songs When Will We Learn and Gi Dem Licks. The first song calls for reflection on Caribbean unity, while the second follows in the tradition of musical showdowns characteristic of calypso.
Much more than just a calypso champion
While his victories have built his reputation, De Bear also devotes part of his time to teaching Montserratian traditions. In August 2025, the Montserrat Arts Council appointed him as a trainer for its Cultural Development Project, a program designed to strengthen the transmission of local artistic practices. Alongside musician Herman “Cupid” Francis, he is participating in this initiative, which combines music education, youth mentoring, and heritage preservation.
His work focuses particularly on traditional masquerades. He works with schools and community groups—notably in Davy Hill—to teach the movements, rhythms, and meanings of this tradition. The results are already evident. In December 2025, several groups of young dancers performed at the opening of the Montserrat Carnival. These performances demonstrate the efforts being made to ensure the continuity of this tradition. For De Bear, the challenge is also to keep these traditions alive outside of the major annual festivals.
Masquerades: A Cultural Heritage to Be Passed On
In Montserrat, masquerades hold a special place in popular celebrations. Originating from African practices that developed in the context of slavery, they have gradually incorporated European influences, particularly certain movements associated with Irish dances. Colorful costumes, masks, percussion, and the fife accompany choreographed dances, many elements of which evoke the island’s colonial history.
Today, this tradition is an important expression of Montserratian identity. Its transmission relies on artists who are able not only to teach its techniques but also to explain its history to younger generations. It is precisely in this area that De Bear’s commitment takes on special significance. By sharing his knowledge, he helps preserve a cultural practice that cannot survive solely through archives or occasional performances.
The award, to be presented in December, thus recognizes a career in which artistic creation and the transmission of cultural heritage are closely intertwined. For Montserrat, it also reflects a commitment to ensuring a lasting place for those who keep its heritage alive.
Frequently asked questions
De Bear, whose real name is Keithroy Morson, is a calypso singer and songwriter from Montserrat. He has won the Leeward Islands Calypso Monarch title five times, in 2007, 2012, 2015, 2023, and 2026. He also passes on traditional masquerades to younger generations.
He was chosen for his career in calypso and his contribution to the preservation of Montserrat’s masquerades. Since 2025, he has been serving as an instructor in a Montserrat Arts Council program designed to teach these cultural practices, particularly in schools and communities.
The inaugural Legends of Montserrat Cultural Excellence Awards ceremony is scheduled for December 6, 2026, at the Montserrat Cultural Centre. Keithroy “De Bear” Morson will be the first recipient. The event is also intended to involve the Montserratian diaspora in paying tribute to the island’s cultural figures.
