Jesse was born in Johannesburg in 1988. By the time he was six months old he was on tour with his father, the late Johnny Clegg, and between 1988 and 1994 he spent at least 5 months a year on the road.He was a classic road kid and grew up backstage and on tour busses. In 1994 his father’s band broke up and the touring subsided. Jesse schooled in Johannesburg at Crawford College and matriculated with six distinctions in 2006.

In school, Jesse experimented with a number of different instruments – which included saxophone, clarinet, drums and piano until he finally settled on guitar. He started playing when he was about thirteen, focusing mostly on chord structures and simple licks.

Early on, Jesse carved out an independent direction for himself in the rock genre, very different from the world music style developed by his Dad.  As someone who grew up in the environment of a successful musical father, he strived to express himself in the most authentic way possible and understood the importance of being able to perform live.

In high school, he began performing as a solo act with just acoustic guitar and voice. He performed at regular school concerts and small clubs. He also joined a number of different bands and experimented with an electric guitar. At around sixteen he began to write his own material. By seventeen, songwriting was his musical focus and it was in this period and the years to follow that he honed his writing skills and put together the songs recorded on the first album.

After Jesse matriculated, he took a gap year in order to record more demo tracks and finally put together an album. He also started a band where he got the opportunity to rehearse and perform some of the songs around Johannesburg – appearing under a number of different band names. It was here that a few of the songs took shape in terms of arrangement and guitar sounds. By this time, Jesse was looking to professionally record the songs with producer, Brian O’Shea who joined the project and they began work on what was to be the final album ‘When I Wake Up’.

The highlight of Jesse’s career came in June 2007 when he got the opportunity to tour internationally with his father Johnny Clegg once again. He performed alongside his father at a number of festivals in France to crowds of more than ten thousand people. Another highlight for Jesse was when a major Belgian producer, Nicolas Fizman, agreed to co-produce the album alongside Brian O’Shea. By the end of 2007 the album was completed and in early 2008 signed a major record deal with David Gresham Records.