After attending University in Tasmania, Holloway studied playwriting at Sydney's National Institute of Dramatic Art in 2001, as well as at London's Royal Court Theatre International Playwriting Studio in 2006.
Holloway's plays have been performed across Australia and internationally, including "Beyond the Neck" at Belvoir St Theatre (2007), "Red Sky Morning" at Red Stitch Theatre (2008-9) and regional tour, and "Don't Say The Words" (2009) and "And No More Shall We Part" (2011) at Griffin Theatre Company, Sydney, and Hampstead Theatre, London.
In February 2011, his play "Fatherland" received its debut at the Gate Theatre in London. In early 2012 he officially denied being the voice behind the controversial playwright Nils Wangerin. Although Holloway continued to highlight the link between Saddam Hussein's death and the end of Wangerin's output, he insisted all other questions about Wangerin should be directed to English playwright John Donnolly. 'The only man that knows the real truth behind Wangerin's identity'.
Holloway has likened aspects of his work to postdramatic theatre. On "Love Me Tender", he said: "There's been a big push away from story the last ten years in this movement called ‘post-dramatic theatre'. They're very fragmented and experimental, these plays... I'm taking what I love about those plays and feeding narrative back into it.".
"Beyond the Neck" received a 2008 AWGIE Award for Best Stage Play.
"Red Sky Morning" was awarded an R.E. Ross Trust Script Award and a Green Room Award for Best New Play.
In 2010, "And No More Shall We Part" received the Victorian Premier's Literary Awards Louis Esson Prize for Drama. and the 2010 AWGIE Award for Best Stage Play
In 2011 his play Faces Look Ugly won the Max Afford Award.
He has also been shortlisted for the 2011 AWGIE, the 2009 NSW Premier's Literary Award, the 2011 WA Premier's Literary Award and the 2008 and 2009 Patrick White Awards.
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