Before becoming more well-known as a composer and singer of music influenced by 1950s and 1960s rock and roll and rhythm and blues, Simon David Cranstoun was a British singer who spent many years performing as a busker on the streets of London and in the Dualers, a ska band he formed with his brother Tyber. The birthplace of Simon Cranstoun is Caterham, Surrey. In the 1960s, Bill Cranstoun, his father, championed Jamaican music. Si also adored R&B and rock music from the 1950s and 1960s. He was selected as the lead singer for his high school band because of how many songs he knew. When he was 16 years old, he started writing songs. A ska band called the Dualers was started by Cranstoun and his brother Tyber. Cranstoun performed on the streets of London for twenty years and once received thirty pence from Prime Minister Tony Blair.

When Cranstoun was performing in Croydon, he met his wife Tamu. They have a son and a daughter. In 2010, he left the Dualers. He chose a more rock or rhythm and blues-influenced sound. He founded a band, which eventually got hired to play in bars and other local places. They basically saw me as a reggae musician doing bebop and were a little bit like, "What is he doing here" he said of the challenge in getting started. He gave a Las Vegas performance in 2013 alongside Little Richard. In April of that year, he was discovered, and he signed with Warner Music's East West label. His album Modern Life peaked at number 30 on the OCC UK Albums chart in October 2014, and his single "Caught in the Moonlight" was selected for the BBC Radio 2 playlist..

How to hire Si Cranstoun for an event