They started off playing at house parties and small clubs, moving through to a residency at Chimes nightclub in Hackney in 1996.
By 1998, they had joined the pirate radio station, Mission 90.6 FM, pioneering a mix of R&B, hip-hop, jungle and dancehall derived sounds, taking its cues straight from the Jamaican sound system tradition, while adding fresh and modern elements from UK garage. In 2002, they signed to BBC 1Xtra, where they presented their Sunday evening programme. They also released a debut compilation album, Heartless Crew presents Crisp Biscuit Vol 1, closely followed by their debut single, “The Heartless Theme aka ‘The Superglue Riddim’”. The single reached number 21 in the UK Singles Chart in May 2002. The music video for “The Heartless Theme” was directed by Andy Hylton. They left 1Xtra in 2006.
It was announced on 1 January, 2011 that the Heartless Crew split up, to pursue solo careers whilst still remaining friends.