Jessamy began her performing life started as a dancer at the age of 6, sharing the stage with her peers in the Octagon Theatre. Since then, Jessamy has been singing, acting, dancing and playing instruments in front of a variety of audiences. 

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Jessamy performed with Castaways Theatre group for eleven fantastic years. During her time at Castaways Jessamy had the pleasure of playing the lead roles, such as ‘Dorothy” from the Wizard of Oz, ‘Peter Pan’ in Peter Pan (flying experience) and ‘Blousey brown’ in Bugsy Malone - Won best Youth in Lead Role - David Beach Awards Somerset. Jessamy also performed with Castaways at a range of different West End theatres, such as Her Majesty’s Theatre, Drury Lane Theatre and the O2 Arena. In 2017 Jessamy performed as a lead soloist and dancer at Disney Land Paris with Castaways which was a highlight of Jessamy's time with Castaways.

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Jessamy has been performing with Yeovil Youth Theatre for six years. She joined Yeovil Youth Theatre at the age of 12 and in her first production with them she was cast as ‘Annie’ in ‘Annie the Musical. For this production Jessamy won the "Best Female Under 16" at the David Beach Awards Somerset. Jessamy continued to perform with Yeovil Youth Theatre for many years and took on many different roles such as, ‘Gertrude McFuzz’ in Suessical, and ‘Brooke Wynndham’ in Legally Blonde.

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At school, Jessamy took part in many performances. Jessamy portrayed the character of "Alice" in "Alice and Wonderland" at the age of 12. She also played the part of "Doralee" in "9 to 5" which is one of her favourite roles she has played. In her final year at school Jessamy performed in a Greek Tragedy. The production was called "The Penelopiad" in which she played the alive version of "Penelope". At the college Jessamy is currently studying at, she has recently been cast as "Wednesday" in the Addams family which they are hoping to perform this spring/summer. 

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Jessamy has performed with the Youth Music Theatre UK in the summer of 2017. She joined the cast of "A Teenage Opera" and the music was by Mark Wirtz. They rehearsed for two weeks and performed the show for a week. The following year Jessamy attended a two week course of intense workshops in London and successfully became a member of the National Youth Theatre.