Michelle A. Henry is one of Trinidad and Tobago’s leading contemporary cultural voices — a calypsonian, vocalist, saxophonist, and cultural practitioner —whose career spans more than two decades.
Singing since age six, Henry told Caribbean Life on Jan. 5 that she formed an early, lasting relationship with the performing arts, viewing it as purpose: Music that tells people’s stories and documents social, political, and moral realities.
As a child, Henry won numerous junior competitions and represented Trinidad and Tobago on international stages, including Notting Hill Carnival.
She said these experiences confirmed her calling and laid the foundation for a career marked by excellence, integrity, and dedication to culture and community.
She said these experiences confirmed her calling and laid the foundation for a career marked by excellence, integrity, and dedication to culture and community.
A trained saxophonist, Henry benefitted from mentorship by leading figures in the performing arts.
She said her artistic development was shaped by the guidance of her music teacher/coach Anthony Woodroffe, Sr.; Dr. Roy Cape; Dr. Leroy Calliste (Black Stalin); Errol Ince; Dr. Ray Holman; Dr. Hollis Liverpool (The Mighty Chalkdust); and Aldric Farrell (Lord Pretender).
She said her artistic development was shaped by the guidance of her music teacher/coach Anthony Woodroffe, Sr.; Dr. Roy Cape; Dr. Leroy Calliste (Black Stalin); Errol Ince; Dr. Ray Holman; Dr. Hollis Liverpool (The Mighty Chalkdust); and Aldric Farrell (Lord Pretender).
Henry said these relationships deepened her musicianship and reinforced her understanding of the performing arts as “a living, evolving narrative—one that remains relevant across generations, even as its sound, form, and presentation continue to change.”
Her artistry is rooted in values instilled by her parents and her scholarship.
Her artistry is rooted in values instilled by her parents and her scholarship.
She earned a master’s degree in cultural studies and a BFA in music from the University of Trinidad and Tobago, integrating academic research with professional practice.
Henry said her spiritual background and early musical training strengthened her desire to reach people meaningfully, using sound, rhythm, and lyric to “connect, challenge, motivate and inspire.”
Henry said her spiritual background and early musical training strengthened her desire to reach people meaningfully, using sound, rhythm, and lyric to “connect, challenge, motivate and inspire.”
Known for her understated stage presence, sharp vocals, and resonant performances, Henry commands attention through substance over spectacle.
Her powerful, electrifying performances and assured stage presence often earn encores, showing her ability to connect authentically with audiences.
Her powerful, electrifying performances and assured stage presence often earn encores, showing her ability to connect authentically with audiences.
Her style seamlessly blends groove-driven melodies with rich, bass-forward arrangements, drawing inspiration from her dual roles as both vocalist and instrumentalist.
Henry said she sings with conviction, addressing political, social, and national issues, guided by a belief that “all aspects of life are interconnected and must be confronted when necessary.”
Henry said she sings with conviction, addressing political, social, and national issues, guided by a belief that “all aspects of life are interconnected and must be confronted when necessary.”
Her catalogue demonstrates a lifelong commitment to the performing arts, serving as a guiding force, commentary, and moral compass.
From her junior years, Henry said songs such as “The Solution,” “Check Yuh Self,” “A Divine Plea,” “No Competition,” and “Who Is to Blame” revealed an early sense of responsibility to the art forms.
From her junior years, Henry said songs such as “The Solution,” “Check Yuh Self,” “A Divine Plea,” “No Competition,” and “Who Is to Blame” revealed an early sense of responsibility to the art forms.
She said her later works — including, “Ask Yuh Self,” “Artificial Intelligence,” “Uncle Roy,” “Assassination Plot,” “What Causing That,” “Big Country Song,” and “Ken”— “continue the tradition of vision, social consciousness and fearless commentary.”
As a musical leader, Henry was musical director for Queen of the Road: A Calypso Rose Musical (2024), which she called “a profound honor.”
Henry founded a female saxophone quartet and leads Michelle Henry & Encore, expanding spaces for musical excellence and representation.
Her lyrics earned national recognition: second place in Trinidad and Tobago’s 50th Anniversary Independence Calypso Monarch (2012) with “Our National Watchwords,” Calypso Monarch Finalist and Top 20 Awardee in 2020 with “The Guest List,” and back-to-back Protective Arms Calypso Monarch titles in 2023 and 2024 with “Peace Survey” and “When De Fighting Start.”
Her 2023 calypso, “Peace Survey,” is a powerful statement against violence and crime, promoting unity, reflection, and love during a time of national urgency.
Beyond the stage, Henry said she is “deeply committed to cultural preservation, education, and mentorship.”
Beyond the stage, Henry said she is “deeply committed to cultural preservation, education, and mentorship.”
Through teaching, research, workshops, and her ongoing series “Conversations in Calypso,” Henry said she explores the meaning, history, and relevance of the art form.
Guided by faith and gratitude, she said musical gifts are “meant to be shared to uplift others.”
Guided by faith and gratitude, she said musical gifts are “meant to be shared to uplift others.”
In addition to her artistic work, Henry is a sergeant in the Trinidad and Tobago Police Service Band, using music as a bridge between institutions and communities—extending her commitment to service, dialogue, and national development.
On Saturday, Jan. 3, 2026, Henry released her latest song, “Enjoy Your Life,” in Trinidad and Tobago.
She said Ortniel “Tobago Crusoe” Bacchus composed the song, which was arranged and produced by songwriters and music producers Trinidadian Gil Figaro, Sr. and Charles Dougherty, a Jamaican-born, Brooklyn-based saxophonist extraordinaire.
She said Ortniel “Tobago Crusoe” Bacchus composed the song, which was arranged and produced by songwriters and music producers Trinidadian Gil Figaro, Sr. and Charles Dougherty, a Jamaican-born, Brooklyn-based saxophonist extraordinaire.
Figaro, chairman and founder of New Jersey-based Sunshine Awards, also wrote the hits “My Mother’s Hands” and “Four Times Blessed.”
Recorded at Krystal Sounds Recording Studio in Brooklyn, Henry said “Enjoy Your Life” carries a “deeply personal meaning,” as it is dedicated to her father, Clive “Chico” Henry.
Recorded at Krystal Sounds Recording Studio in Brooklyn, Henry said “Enjoy Your Life” carries a “deeply personal meaning,” as it is dedicated to her father, Clive “Chico” Henry.
The chorus goes: “Enjoy your life/Enjoy your life/You never know how much longer you will survive/Just do what you have to do/And above all yourself be true/Because you never, never, never, know/When the sun going to set on you.”
Through her leadership, voice, instrument, scholarship, and service, Henry carries the performing arts conscience forward—honoring legacies while ensuring its relevance for future generations.
