After he completed his studies, Jordaan spent a year as an entrepreneur. In October 1998, he moved from the Cape to Pretoria and, after gaining popularity in the city, recorded his debut album, Vreemde Stad, in Stellenbosch. This album was released in 2000 at the Klein Karoo Nasionale Kunstefees in Oudtshoorn. EMI released Vreemde Stad shortly afterwards, and the album surpassed triple platinum status (150 000 copies) in July 2003.
He launched his second album, Tjailatyd at the Aardklop music festival in 2002, which also sold more than 150 000 records. The South African guitar player, Anton L'Amour, performed with Theuns and was responsible for all the guitar tracks in Vreemde Stad and Tjailatyd.