‘This one is special’: De Bear delivers Montserrat’s first Leeward Islands calypso crown

Photo credit: Facebook
Keithroy "De Voice" Morson of Montserrat edged out local favorite Queen Roxxy to win his fourth Leewards title.

When Keithroy “De Bear” Morson finally got a chance to check his phone following the frenzy of his latest calypso victory, about 50 text messages awaited him. They came from Montserrat, Antigua, the United States, the UK and elsewhere. Never mind it was after 2 a.m. Family, friends and fans fought off sleep and time-zone challenges to celebrate another big win for the little master.

Morson added to his legacy as a calypso virtuoso when he captured the Leeward Islands Calypso Monarch title in the early morning hours of Sunday, August 13, 2023 in Anguilla.

Performing as “The Voice” – instead of his customary moniker “De Bear” – Morson outclassed seven regional rivals at Landsome Bowl in The Valley. It was his fourth Leewards crown but his first representing Montserrat, his home country. His three other wins came for Antigua, where he relocated in wake of the volcanic crisis in the late 1990s.

“This one . . . for Montserratians . . . is bigger than the three for Antigua,” he said. “This one is special. This is for home.”

It was Montserrat’s first regional calypso title since Justin “Hero” Cassell won the Organization of Eastern Caribbean States (OECS) crown in 1986 in Dominica.


The Leeward Islands Calypso Competition, which began in 1997, was contested for the first time since 2019. The event was canceled in 2020 and 2021 due to COVID and was scrapped last year because of low registration.

The show returned in high standard as eight competitors duked it out. Morson sang Don’t Wake The Bear and Hard Like A Diamond, songs he won with in Montserrat in 2021 and 2022, respectively. But he altered the lyrics of both to make them palatable for a regional audience. Participants in the Leeward Islands competition have often faced the conundrum of tweaking songs that address issues in their particular island. Morson adjusted his lyrics and delivered them seamlessly.

In Montserrat, Don’t Wake The Bear targeted his longtime rival, King Kenzie. But in Anguilla, it was aimed squarely at local calypso monarch Roxanne “Queen Roxxy” Webster.

“In 2019 Roxxy and I were tied in the Leewards competition and they gave her the crown,” Morson says. “She went on the radio boasting that she knows how to beat the Bear. So I was planning for her since last year but that show was canceled.”

Singing in the No. 3 position, De Bear sprinkled Don’t Wake The Bear with picong toward Roxxy in the second round. When she performed Women Doing That Too in the No. 6 position, she addressed the Bear in her final verse, but her banter was lukewarm compared to De Bear’s protracted lyrical scolding.

At least two other competitors – Richie Buntin (St. Thomas) and Young Destroyer (Antigua) – mentioned De Bear in their second-round songs, a likely sign that they sensed he was the front-runner.

Roxxy eventually finished first runner-up, with Young Destroyer second runner-up. The other competitors were Miss Independent (St. Kitts), King Hollywood (Nevis), Mighty Dow (St. Maarten) and Queen Blackness (St. Croix).

De Bear says despite the minor verbal jousting, all the contestants were cordial and personally congratulated him afterward. Roxxy even joined De Bear on stage following the results and sang along to Don’t Wake The Bear.

Photo credit: Facebook
Keithroy “De Voice” Morson celebrates his victory with backup singer Ronel White and Montserrat Arts Council director Kenneth “Rabo” Silcott.


Asked where this victory ranks in his career, De Bear says it’s No. 2 overall.

“No. 1 will always be my victory in 2007 in Antigua. It was my first win there. It was no easy task. To get that crown after six years of finishing first runner-up, second runner-up . . . I don’t think anything will top that one for me.”

As an aside, Morson’s victory should quell any lingering hard feelings from 2015. That summer, he held dual crowns in Antigua and Montserrat, but when he competed at the Leewards show he represented Antigua. That drew the ire of many Montserratians, some of whom likened it to treason.

But those sentiments were not evident late Saturday. Hundreds of Montserratians tuned in on radio or watched via pay-per-view until the wee hours. They posted countless congratulatory messages and shared videos of his performance. A watch party was even held at Scoreboard Sports Bar in Little Bay.

As for where his calypso career goes from here, De Bear suggested he might be at a crossroads.

“As far as calypso, I’ve been there and done that. I want to be put in a position to scout talent and pass on my knowledge to the youths. Arrow didn’t get to do it and now he’s gone. Ruler didn’t get to do it and he’s gone. But first I need our government to see the importance of doing it.”

De Bear says he would also like the Government of Montserrat to show an appreciation for his accomplishments. Something tangible rather than symbolic would be nice.

“I don’t want no MBE or OBE,” he says. “I want Montserrat to give me the respect I deserve as a son of the soil.”

Calypso crowns by De Bear (De Voice)

Year EventSongs
1985Montserrat Jr. CalypsoSlavery (one song)
1992Montserrat FestivalBack to Basics & Face The Truth
1993Montserrat PilgrimageCome Home (one song)
1993Montserrat FestivalThe Time Has Come & Show Respect
2002Antigua IndependenceMan Is Dust & Help
2007Antigua CarnivalI Say No & Support Party
2007Leeward Islands CompetitionI Say No & Man Is Dust
2010Antigua CarnivalLeopard Come Home & Don't Sing Bout de Judgment
2011Antigua CarnivalMelee For Sale & We Get The Change Ivena
2012Antigua CarnivalTime To Take Our Place & Freedom for Mandela
2012Leeward Islands CompetitionTime To Take Our Place & Freedom for Mandela
2014Montserrat FestivalDon't Forget Your Juliet & Got To Go
2015Antigua CarnivalCan't Stop The Bear & Sing A Different Song
2015Leeward Islands CompetitionCan't Stop The Bear & Sing A Different Song
2019Antigua CarnivalLet The Master Show You & On A Ray Of Hope
2020Montserrat CarnivalBy Faith & Call Daddy
2021Montserrat CarnivalLet Us Rebuild & Don't Wake The Bear
2022Montserrat CarnivalHard Like A Diamond & Ah Shoulda
2023Leeward Islands CompetitionHard Like A Diamond & Don't Wake The Bear

Montserrat Notable Regional Titles

1951Leeward Islands Cricket Montserrat
1953Leeward Islands Cricket Montserrat
1986OECS Calypso MonarchJustin "Hero" Cassell
1987Caribbean Talented TeenStacy Richards
1987OECS Queen ShowPauline Wall
1988OECS Queen ShowJemma Neptune
2015Caribbean Jaycees QueenSharissa Ryan
2023Leeward Islands CalypsoKeithroy "De Voice" Morson



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