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Kay became known to the public when he won the newcomer's competition, 'So You Think You're Funny', at the Edinburgh Festival Fringe in 1989. He then went on to be nominated for the prestigious Perrier Award in 1993. He won the award for Best Stand-Up at the British Comedy Awards in 1994.
Kay continued to work worldwide as a live stand-up, most notably on regular and very successful tours of the Adelaide Festival and Melbourne International Comedy Festival in Australia.
Following his rise to comedic fame, Phil went on to be comedic (though not on stage) selling books in Halifax, Nova Scotia. In April 2012, his show at Aberdeen's Blue Lamp was cut short. He was later rebooked, making a virtue of Kay’s notoriety, billing the gig as The Meltdown Part II and actively encouraging punters to stay away. This time, the venue, Snafu, was a lot happier, posting on Facebook afterwards: ‘Phil Kay... what can I say. Absolutely stormed it at Breakneck Comedy tonight!’  In August 2011 and 2012 he performed sold out runs at the Edinburgh Fringe performing on Bob Slayer's Alternative Fringe.
Kay hosted his own stand-up comedy series on Channel 4 in the UK called Phil Kay Feels..., recorded in front of a live audience in 1997. His other works on television have included Next Stop, Phil Kay (also on Channel 4), Edinburgh Nights (BBC1) and The Montreal Festival of Fun (Channel 5). In conjunction with filmmaker Archie Lauchlan, he also released That Phil Kay Video onto the retail market in 2000. This unique collection of Kay's live standup gigs was re-released in 2014 via Video On Demand (see vimeo.com/ondemand/thatphilkayvideo here).
He has remained largely behind-the-scenes on television to date, with writing credits including Jonathan Ross's Saturday Show, Channel 4's Viva Cabaret, The Smell of Reeves and Mortimer, Sean's Show, Harry Hill's Pilot Show, and many more. He has appeared as a panellist on the BBC television show QI. On 19 November 2009, he appeared as the stand-up act on the BBC Three television show Russell Howard's Good News.