[5] Living in Gillman Barracks in his early childhood, Choy found himself immersed in music of different languages, such as English, Malay, Tamil, Mandarin and Hindustani.

Choy attended Pasir Panjang Primary School, where he learnt how to play a recorder and a guitar, and together with his brother, James, they were known as the Cyclones, eventually pioneering the local R&B scene.

[9][10] Choy was also a pole vaulter, and he won first place in an interschool competition after being the only athlete competing in his division, setting a school record of 2.29 m (7 ft 6 in).

[10][12][13] In 1964, the Cyclones joined the Checkmates to be their lead vocalists, performing regularly at tea dances organised by the Golden Venus club located along Orange Grove Road in Tanglin.

[9][16] Upon graduation from university, Choy worked as a journalist for Fanfare, an entertainment magazine published by Straits Times Press.

[10] In 1991, together with comedy group Kopi Kat Klan, Choy released an album titled Why U So Like Dat?, consisting of Singlish songs and sketches.