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LeAndra Head, a rising concert star

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Newsday LeAndra Head performs at North Coast Jazz held in Blanchisseusse on May 27-29. Photo courtesy Andrea De Silva. -
LeAndra Head performs at North Coast Jazz held in Blanchisseusse on May 27-29. Photo courtesy Andrea De Silva. -

VISHANNA PHAGOO

LeAndra Head’s most memorable musical performances are at the Porgy and Bess opera in Budapest; in Hungary with Living Arts International Inc in 2013; and at the 2019 Tobago Jazz Festival. And, she told WMN, her recent performance at North Coast Jazz on May 27-29 has been added to that list.

"The audience was just very warm and I really enjoyed performing for them," the 28-year-old told WMN of the experience.

She said although she was a "bag of nerves," as it was her first time performing at this festival, it was wonderful. She even included a new song in her playlist – one of her and her mother’s favourites, First Time Ever I Saw Your Face, by Roberta Flack.

She said it was a long-awaited request by her mother after Head had been away from the stage for so long.

After her performance she received a lot of compliments, but one especially stuck with her. While walking through the flea market at the event she was stopped by a vendor at a stall who told her her performance had left everyone emotional.

"She said I performed a song that one of the customers didn't even like, but they liked how I did it, and they were all crying during my performance."

LeAndra Head and John Thomas at Reflections. Photo courtesy Andrea De Silva -

This, said Head, brought back memories of her performance in Hungary, which was special because it was her first time travelling there to perform, and could be considered the pinnacle of her career, since she was the youngest in the entire cast.

"After one of the performances, the other performers and I were passing through an alleyway that took us to the restaurants. People started clapping for us and shouting, 'Bravo,' and 'You did so well.'"

As for the 2019 Tobago Jazz Festival, she said, she was expecting her performance to be a disaster because her flight was delayed and she had to rush to the venue. But all her doubts faded when she began to sing.

"I felt like the audience and I were best friends by the time the performance was over."

Head is the daughter of photographer Andrea De Silva and former US Marine Corps Master Sgt Leroy Head Jr. She has been singing since she was nine. Her first public performance was the popular children’s talent contest Twelve and Under, where she placed second with Somewhere Over the Rainbow.

This performance earned her the Joy Caesar trophy, awarded to the series’ most outstanding vocalist.

She also won the St James We Beat festival’s amateur night competition in 2003, and that same year sang at the San Fernando Jazz Festival alongside South African performer Hugh Masekela. She dazzled the audience with her soulful version of Etta James’ signature hit At Last.

She took a break from performing in her early teens, but reignited her passion in March 2013 when she sang at an open-mic event at the popular Sugar Bar in Manhattan, New York. She was invited to return to do her own set on another night.

LeAndra at Adan Hagley's show. Photo courtesy Andrea De Silva -

She received an "honourable mention" at the TT Classical Music Development Foundation's 2015 opera competition for her performance of Les Berceaux and Batti Batti O Bel Masetto.

As with so many other entertainers worldwide, the covid19 pandemic took its toll on Head personally and professionally. Initially, she enjoyed the first few months of the 2020 lockdown and focused on plants and helping her mother in her garden.

"I was doing really well for the first six-eight months, because I was home with my books and my movies. I was just very content."

After a while, though, the situation became "brutal" and she especially missed the stage.

But she managed to find a silver lining and began performing for viewers on Instagram live and turned this into a series, Your Request Live. She’d reach out to her followers, who would comment their song requests, which she would perform then and there.

"It was great, my followers were enthusiastic and it was well received. I couldn't see their faces, which was weird, but I saw their reactions through comments and emojis, which felt good. And I never got a weird request, thankfully."

LeAndra Head at Brian Mac Farlane's Christmas Joy. Photo courtesy Andrea De Silva -

Although she was not always consistent, people enjoyed the series, which ran from 2020-2021. She was just glad she could bring some sort of happiness to the public, which in turn made the lockdowns more bearable.

Head now offers one-on-one vocal classes at her Glencoe home, three days a week, to anyone interested. She said most of her students are performers who seek her help in areas in which they are not strong. She tailors all her classes to the requirements of each student.

Her future plans will always include singing and performing, but she said the uncertainty caused by the pandemic has prevented her from making any solid plans just yet.

She does have one lifelong dream, though.

"If I have one thing I could say I'd happily die right after, it would have to be voicing a Disney princess, or to even be a part of something similar."