Simon is one of the many Zim musicians who have have found their footing in bands before heading out to pursue solo careers. Chimbetu first found success in the Marxist Brothers. Formed by Simon, along with his brothers Naison, Brian
and Allan, the band had a string of hits during the 1980s and early 1990s. Despite backing Simon on his first solo effort, Karikoga, The Marxist Brothers eventually dissolved in the mid-90s as the members left to pursue their own careers, while others joined Simon's backing band, Dendera Kings. This set the stage for Simon to assume the position of one of Zimbabwe's premier rhumba artists.
Taking the torch from acts such as Jonah Moyo, Chimbetu hit stardom with albums such as Survival, and Lullaby. Compared to most Zim rhumba, Simon's songs feature guitar solos sandwiched between prominent vocal lines and repetitive guitar riffs. His music is similar to that of his earlier band, the Marxist Brothers, as well as popular rhumba musician Leonard Zhakata. His songs tend to focus on the working class and the poor; unsurprisingly, Chimbetu has come out in supprt of the recent land grab.
Simon hasn't been far from controversy during his career. At the peak of his popularity, he spent four years in jail after being convicted of car theft. Rumours hit, in 2002, that he hadn't paid his farm workers for months. Additionally, his pro-government stance, as well as the waning popularity of rhumba, has not endeared him to fans of late.