Whitehead's debut single "I Don't Do Surprises" was released on radio during January 2008, debuting at #8 on the ARIA Charts in Australia on 17 March 2008. Also reaching No.1 of Australian ITunes charts. It has also received airplay on Nova radio and surfaced on TV advertisements for popular Channel 10 shows House and Women's Murder Club, and Channel 7's Home and Away, being described as a cross between Coldplay and Robbie Williams. His debut album, Losing Sleep was mixed by UK mixer, David Treahearn and released through Roadshow Music on 22 August 2008. Whitehead made his return to Video Hits on 24 February 2008, and to Australian Idol on 5 September 2008, though only as a guest to promote his debut album. The third single off Losing Sleep, Satellite has received significant play on Channel V and Video Hits.