In 1999 Whitehead was accepted into the Victorian College of the Arts to study Jazz Improvisation, then toured Australia and China with various bands.

In October 2006, Whitehead was sacked as TV presenter of Video Hits after exposing himself on stage during the ARIA Music Awards.

[6] 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.

Whitehead's first acting roles were minor parts in the television series The Secret Life of Us, and the 2003 film, Ned Kelly.

[7] After taking acting lessons for eighteen months, Whitehead auditioned for a role in Home and Away, which he described as "such a great place to learn and hone your skills".

[13][14] He played an Australian rock singer named Davis, a love interest of Fiona Gallagher (Emmy Rossum).

[17] In 2021, Whitehead appeared on season three of The Masked Singer Australia making it to the Grand Finale and finishing in third place as "Mullet".

[18] Sarah Oakes, Cleo Editor-in-chief denied the claims that Whitehead won as a direct result of a self-marketing ploy; "[He] is that perfect combination of good looks, charm, charisma and the kind of guy you'd be really happy to take home and introduce to your mum.