At that point we used to play the gig with our beats recorded on a walkman that we'd plug through the PA." – Optamus[10] The group added a third MC, Dazastah (Darren Reutens), whom they met at Leederville TAFE, and DJ Armee (Damien Allia) on turntables, meeting him at the Hyde Park Hotel where he would DJ on Monday nights.
Cheetham recalls "I was in Tokyo hanging out and got a call from my mate Sal, he's playing drums with these guys Downsyde and he said 'when you come back you should have a crack at sampling stuff for them.'
– Cheeky[10] For four years Downsyde produced beats and rhymes and played at hundreds of gigs, parties, and MC battles culminating in the September 2000 release of their debut album, Epinonimous – recordings made by the band from 1996 to 2000.
[16] Downsyde signed with Obese Records and in 2004 released a single, "Lesfortunate", which they followed up with a third album, When the Dust Settles, in December 2004.
Catastrophe was a short-term member and filled in to do the late 2005 "When The Dust Settles" Australian Tour and performances up to mid 2006.
Downsyde was one of the Australian hip hop artists featured in the documentary Words from the City, which aired on ABC Television in late 2007.
It just happened that Illusive came back with a very interesting way of marketing Downsyde, plus we have the common goal of elevating us as a band and not Australian hip hop per se."
– Optamus[22] The group's fourth album, All City was released on 4 October 2008, and features collaborations with Howling John Stone and Guru.
The first single from the album "Fortune and Fame" was released on 1 September, together with the accompanying video produced by West Australian production company The Penguin Empire has received significant airplay.
[24][25] Of the tour, the band said "We're pumped man – it has been a long time since we did a string of dates around the country, and it's good fun."
As Downsyde, we've got about eight or nine tracks in demo form for the new album, which we're hoping to finish – at least written-wise – by the end of the year.Downsyde has been on a five-year hiatus.