Kerr worked as a staffer to Howard government cabinet members Robert Hill, Amanda Vanstone and former South Australian Premier John Olsen and corporate relations manager for construction giant Baulderstone Hornibrook.
Kerr was author of Crikey's "Hillary Bray" column (named after an identity used by James Bond) before starting to write under his own name from mid-2004. In 2008 he joined Rupert Murdoch's The Australian.
He is a columnist for the publication of an Australian conservative think-tank Institute of Public Affairs Review; a contributing editor to the Australian edition of The Spectator; and a regular guest on ABC Radio National's Late Night Live with Philip Adams, ABC News Radio, Sky News Australia, ABC Television News Breakfast, ABC News Radio and radio stations 774, 2GB and 5AA. Kerr has also been a guest on the BBC World Service, Radio New Zealand and Al Jazeera and commercial and ABC radio in all Australian capital cities, as well as regional centres.
He has been a contributor to GQ, Rolling Stone and Quadrant magazines, The Age and The Sunday Age and the Adelaide Sunday Mail; a columnist for News Limited's suburban papers and has appeared on the 7:30 Report, the 7PM Project, Channel 9's Sunday program and Today Tonight.
Kerr has been at the center of recent controversy concerning plain packaging of cigarettes in Australia, after writing an article for The Australian that erroneously stated cigarette consumption had increased since this measure was introduced. 
Kerr again caused controversy after he authored a short article published in the Australian newspaper on December 4th 2014 titled "Senator Waters' girl dares to wear pink" which featured a photograph of the six-year-old daughter of serving Senator Larissa Waters, taken without permission from the Senator's Facebook page. The purpose of the article was to highlight the colour and nature of the child's dress, and imply that the Senator had double standards because the Senator had recently made unrelated comments in the media regarding the gender marketing of toys. 
- The Age, July 2004
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