In 2023, Jesse Clegg was the main support act for Imagine Dragons on their 2023 stadium tour to more than 130 000 people in South Africa. He also performed with platinum selling US pop band WALK THE MOON in the US to an audience of 60 000 people. He performed a special event for the Springbok rugby team as part of their homecoming tour after their high-profile victory at the Rugby World Cup in 2023. That same year, Clegg released chart-topping single Called To Hear Your Voice to critical and commercial acclaim. The song was recorded in LA with Grammy-winning producer Tim Pagnotta.

In 2024 he released the single "Home” featuring Msaki and Grammywinning Autumn Rowe (songwriter on Jon Batiste's We Are - 2023 Grammy's Album of the Year). The three of them performed the song together at multiple events during the course of the year.

Jesse Clegg's most popular singles include Let It Burn, Speed of Light, Waiting on the Outcome, Today, Use Me, Breathing (featuring Shekinah), and recently Called to Hear Your Voice. Clegg also featured and co-wrote the hit single Fire In Your House by US pop group WALK THE MOON. Jesse shared the stage with his father, Johnny Clegg, in 2016 and they subsequently performed three world tours together. In 2018, Jesse cowrote and executive produced his father's final album, 'King of Time'. Jesse's commitment to using music as a platform for positive change is showcased with his role as an official ambassador for the Nelson Mandela 46664 foundation. A significant accolade that is soon to be added to Clegg's career is his upcoming headline performance at Carnegie Hall in New York City. The iconic venue is considered to be a pinnacle of live music performance halls globally. Clegg will perform there on 29 October 2024.