[6] At the beginning of her music career, the singer originally took the name Crusoe Kid but later changed it to Calypso Rose.

[9] Calypso Rose was the fourth child to be born by her mother, Dorchea Sandy, who had a total of thirteen children, two of which passed away.

[9] To this day, Calypso Rose says she drinks seamoss, and eats a lot of fish, ginger, garlic, and banana to give her the energy to put on a powerful show.

Her aunt, Edith Robinson, was wanting a child so she suggested to her husband that he go to his brother, Altino Sandy, and ask to take care of one of his children.

Rose then began to write her first calypso called "Glass Thief" which signified her shock to Trinidad after her aunt gave her money and told her to go to the market where she saw boys stealing eyeglasses from someone's face.

[16] Even with many of the religious elders in Trinidad's disapproval for Rose's participation in calypsos, she was able to win them over with her song "Abide With Me" which is about hurricane Florence that hit Tobago and Grenada in 1964.

In 1966, she wrote the song "Fire in Meh Wire" that had gone international and was translated into eight different languages, and was the first calypso to run two years in a row at the Trinidad Carnival.

In 1979 Calypso Rose performed in a concert put on by the Colombia's Caribbean Students' Association and was later reviewed by Robert Palmer (writer) from the New York Times.

[22] Other music legends that she got to meet are Michael Jackson and Miriam Makeba in 1978 when she won Trinidad Road March.

[24] The two were first introduced when her manager, Mr. Jean Micheal invited Chao to the Carnival season in 2015 where Calypso Rose recounted that they spoke for 3 hours about music.

[10] In October 2019, she released a song titled "Baila Mami" from the new Calypso Rose & Friends EP featuring Nailah Blackman, Lao Ra, Manu Chao, Machel Montano, Patrice, Tim Armstrong & The Interrupters and King Doudou.

Her song "No Madam", about the practice of labor exploitation in the Caribbean, led to the government of Trinidad and Tobago enacting minimum wage for civil servants.

In an interview, Rose said that her two proudest moments in life was when she was named Calypso Monarch and when she won the French Grammy award, Victoire de la Musique, in Paris in 2017 because of her album "Far From Home".