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Tired of working as a public servant, O'Leary began performing stand-up comedy in 2015 in [[Wellington]].[{{cite web |last1=Miller |first1=Ayla |title=Twenty plus questions with comedian Ray O'Leary |url=https://ontherecordco.wordpress.com/2018/09/24/twenty-plus-questions-with-ray/ |website=On the Record |date=24 September 2018}}] By 2018, he was also writing for television shows. |
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Tired of working as a public servant, O'Leary began performing stand-up comedy in 2015 in [[Wellington]].[{{cite web |last1=Miller |first1=Ayla |title=Twenty plus questions with comedian Ray O'Leary |url=https://ontherecordco.wordpress.com/2018/09/24/twenty-plus-questions-with-ray/ |website=On the Record |date=24 September 2018}}] By 2018, he was also writing for television shows. |
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O'Leary has appeared on various [[panel show]]s, including ''[[Have You Been Paying Attention?]]'', ''[[The Cheap Seats]]'', ''[[Guy Montgomery's Guy Mont-Spelling Bee]]'', ''[[7 Days (New Zealand game show)|7 Days]]'', ''[[Taskmaster New Zealand]]'' and ''[[Patriot Brains]]''.[{{cite news |last1=James |first1=Shauni |title=Comedian Ray O'Leary bringing his deadpan and whip-smart humour to Rotorua |url=https://www.nzherald.co.nz/rotorua-daily-post/news/comedian-ray-oleary-bringing-his-deadpan-and-whip-smart-humour-to-rotorua/IHWXHTC6U5B6PKQ3ZTZ53YEFGI/ |work=Rotorua Daily Post |date=19 January 2023}}] Other television programs O'Leary has been in include ''[[Thank God You're Here]]'', ''Raised by Refugees'', ''[[Golden Boy (New Zealand TV series)|Golden Boy]]'', and ''My Favourite Dead Person''. Podcasts he has participated in include ''Waterdeep Mountain High'' and ''Socrates Walks into A Bar''. |
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O'Leary has appeared on various [[panel show]]s, including ''[[Have You Been Paying Attention?]]'', ''[[The Cheap Seats]]'', ''[[Guy Montgomery's Guy Mont-Spelling Bee]]'', ''[[7 Days (New Zealand game show)|7 Days]]'' and ''[[Patriot Brains]]''.[{{cite news |last1=James |first1=Shauni |title=Comedian Ray O'Leary bringing his deadpan and whip-smart humour to Rotorua |url=https://www.nzherald.co.nz/rotorua-daily-post/news/comedian-ray-oleary-bringing-his-deadpan-and-whip-smart-humour-to-rotorua/IHWXHTC6U5B6PKQ3ZTZ53YEFGI/ |work=Rotorua Daily Post |date=19 January 2023}}] Other television programs O'Leary has been in include ''[[Thank God You're Here]]'', ''Raised by Refugees'', ''[[Golden Boy (New Zealand TV series)|Golden Boy]]'', and ''My Favourite Dead Person''. Podcasts he has participated in include ''Waterdeep Mountain High'' and ''Socrates Walks into A Bar''. |
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In 2018, O'Leary and Lucy Roche performed the show ''Young, Dumb and Full of Comedy''.[{{cite web |last1=Longshaw-Park |first1=Rachel |title=REVIEW: Lucy Roche and Ray O'Leary: Young, Dumb and Full of Comedy (NZ International Comedy Festival) |url=http://www.theatrescenes.co.nz/review-lucy-roche-and-ray-oleary-young-dumb-and-full-of-comedy-nz-international-comedy-festival/ |website=Theatre Scenes |date=11 May 2018}}] O'Leary presented his comedy show ''Everything Funny All the Time Always'' in 2023 across New Zealand and then at the [[Melbourne International Comedy Festival]] and the Sydney Comedy Festival.[{{cite news |last1=Low |first1=Lenny Ann |title=The new wave of Kiwi comics ready to tickle Australian audiences |url=https://www.smh.com.au/culture/comedy/the-new-wave-of-kiwi-comics-ready-to-tickle-australian-audiences-20230328-p5cvz7.html |work=[[The Sydney Morning Herald]] |date=31 March 2023}}] |
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In 2018, O'Leary and Lucy Roche performed the show ''Young, Dumb and Full of Comedy''.[{{cite web |last1=Longshaw-Park |first1=Rachel |title=REVIEW: Lucy Roche and Ray O'Leary: Young, Dumb and Full of Comedy (NZ International Comedy Festival) |url=http://www.theatrescenes.co.nz/review-lucy-roche-and-ray-oleary-young-dumb-and-full-of-comedy-nz-international-comedy-festival/ |website=Theatre Scenes |date=11 May 2018}}] O'Leary presented his comedy show ''Everything Funny All the Time Always'' in 2023 across New Zealand and then at the [[Melbourne International Comedy Festival]] and the Sydney Comedy Festival.[{{cite news |last1=Low |first1=Lenny Ann |title=The new wave of Kiwi comics ready to tickle Australian audiences |url=https://www.smh.com.au/culture/comedy/the-new-wave-of-kiwi-comics-ready-to-tickle-australian-audiences-20230328-p5cvz7.html |work=[[The Sydney Morning Herald]] |date=31 March 2023}}] |
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