Chameleone's career began at a young age in 1996 as a DJ at the Missouri night club in Kampala. He was later signed to the Kenyan record label Ogopa DJs, where he broke through with his first single,"Bageya" that featured Kenyan artist Redsan.
Chameleone's musical style is a combination of Ugandan music, central African rumba, zouk, and reggae. His first album, Bageya, was released in 2000. By 2013, he had released twelve more albums, including Mama Mia in 2001, Njo Karibu and The Golden Voice in 2003, Mambo Bado in 2004, Kipepeo in 2005, Shida za Dunia in 2006, Sivyo Ndivyo and Katupakase in 2007, Bayuda in 2009, Vumilia in 2010, Valu Valu in 2012, Badilisha in 2013, Tubonge in 2014, Wale wale in 2015, Sili Mujjawo in 2016, Sweet Banana in 2017, Champion in 2018.