Queen Roxxy: The Crown Collection | 21 Caribbean Crowns
Roxanne “Queen Roxxy” Webster has spent more than two decades proving that a crown is not simply something you wear — it is something you earn, defend, lose, reclaim, and pass on as part of a legacy.
In the world of Caribbean calypso and soca, titles come with pressure. They demand creativity, discipline, stage presence, lyrical intelligence and the ability to connect with an audience. For Anguilla’s Queen Roxxy, those demands have become part of the journey.
And what a journey it has been.
From a young girl known as Lil’ Roxxy to one of the Caribbean’s most accomplished female calypsonians, Roxanne Webster has built a remarkable collection of crowns across the junior and senior arenas.
Today, her résumé tells a story in numbers:
Junior — 8 Crowns
- 5× SXM Junior Calypso Monarch
- 2× SXM Junior Road March
- 1× OECS Junior Calypso Monarch
Senior — 13 Crowns
- 7× Anguilla National Calypso Monarch
- 2× Leeward Islands Calypso Monarch
- 3× Anguilla Groovy Soca Monarch
- 1× Anguilla Power Soca Monarch
That is 21 major crowns — a collection that represents years of competition, growth and an unwavering commitment to Caribbean music and culture.
From Lil’ Roxxy to Queen Roxxy
The name “Roxxy” began simply enough. It came from Roxanne Webster’s nickname, and when she first entered the calypso arena at 10 years old, she performed as Lil’ Roxxy and won with her song, “A Baby’s Cry.” Over time, the name evolved with the artist. Lil’ Roxxy became Queen Roxxy.
But the transformation was about much more than a name.
Born on the French side of St. Martin, Roxxy grew up attending calypso shows with her parents. She followed the footsteps of her eldest sister, Queen B, who competed in the Anguilla Senior Calypso Competition.
A Crown Collection Built Across Islands
What makes Roxxy’s record particularly impressive is that her success has never been confined to a single competition or even a single island.
Her crowns span St. Maarten, Anguilla and the wider Leeward Islands, demonstrating an ability to compete successfully in different environments and against some of the region’s strongest performers.
Her Leeward Islands success, in particular, placed her firmly on the regional calypso stage. In 2019, Roxxy captured the Leeward Islands Calypso Monarch title, adding the regional crown to victories in the Anguilla Calypso Monarch and Soca Rave competitions that same year.
Her regional reputation was already well established before then. In 2016, she finished second runner-up in the prestigious Queen of Queens Calypso Monarch competition in Montserrat, competing against monarchs from across the Caribbean.
Even when she does not leave the stage with the crown, Roxxy has repeatedly demonstrated that she belongs among the region’s elite.
In 2023, she finished first runner-up in the Leeward Islands competition in Anguilla after a spirited clash with Montserrat’s Keithroy “De Bear” Morson.
And in 2025, she again reached the regional final, finishing first runner-up behind Antigua and Barbuda’s Ge’Eve, who became the youngest-ever winner of the Leeward Islands title.
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Seven Times Queen of Anguilla
Perhaps the most significant part of the collection is Roxxy’s record at home.
With seven Anguilla National Calypso Monarch crowns, she has established herself as one of the defining voices of Anguillian calypso.
Her relationship with the national competition has included periods of dominance, reinvention and return.
In 2017, for example, she successfully defended her Anguilla Calypso Monarch title for a second consecutive year.
Then came another major chapter in 2025.
It was a statement.
The Queen had returned to the throne.
More Than Calypso
Roxxy’s crown collection does not stop with calypso.
Her record includes three Anguilla Groovy Soca Monarch titles and one Anguilla Power Soca Monarch crown.
Her ability to move between calypso and soca demonstrates another dimension of her artistry. Calypso demands storytelling, social commentary and lyrical precision, while soca brings its own emphasis on rhythm, energy, movement and crowd connection.
Roxxy has proven that she can inhabit both worlds.
In 2019, she captured the Groovy Soca Monarch title at the Flow Soca Rave, while Mr. Decent took the Power Soca Monarch crown.
That versatility is an important part of what makes her career stand out.
She is not simply a calypso singer who happens to perform soca.
She is a Caribbean entertainer who has repeatedly demonstrated that she understands the competitive arena in all its forms. A true queen does not simply collect crowns; she builds a legacy.
C.V: As a child did you ever imagine that you would achieve all these crowns?
Queen Roxxy: No, I never imagined it would become 21 crowns. As a child, I just loved calypso and loved being on stage. I wanted to sing, compete, and make my family proud. I don’t think Lil’ Roxxy could have understood where that first crown would eventually lead. Looking back now, every crown represents a different chapter..the wins, the losses, the lessons, the growth and the people who helped me along the way. I’m proud of the titles, but even more grateful for the journey and the legacy I’m still building.