Having started stand-up whilst in his final year of Law at the University of Edinburgh, a year which saw him make the final of both the Paramount Funniest Student and Chortle Student Comedian Of The Year competitions, Stirling is a regular on the UK comedy circuit. Having been dubbed one of Scotland's 'Hottest Newcomers' by The Scotsman after his performance in front of 750 people at the Glasgow Fruitmarket, he now gigs all over the UK including The Stand, The Comedy Store, Off The Kerb and various smaller clubs. In August 2009, Stirling performed in the final of the Chortle Student Comedian Of The Year at the Edinburgh Fringe Festival, finishing runner-up to winner Joe Lycett. From October 2012, he toured with Russell Kane as a warm up act for Kane's Posturing Delivery.
TV and Radio
CBBC
After being spotted at a gig, Stirling has since presented the CBBC Channel along with his canine sidekick Hacker T. Dog from the CBBC TV show Scoop, and other sidekicks including Dodge the Dog, 'The Toad of Wisdom', and 'Pig With 'Tasche'. He has also worked as a writer on a number of projects for the likes of CBBC and BBC Scotland. He also appeared in Scoop as the postboy in the first four episodes of the new series. Stirling presents CBBC's show, Help! My Supply Teacher's Magic – the show puts magicians in schools and tricks children into thinking they are teachers. Stirling also presented 12 Again, a show in which celebrities talk about what they were like when they were twelve. Stirling also co-presented All Over the Place from 2011-2015, and in 2017. On 1 February 2013, Stirling left CBBC but returned in September 2015 for CBBC's 30th anniversary.
''The Dog Ate My Homework''
In early October 2013, Stirling began recording for a new series for CBBC, The Dog Ate My Homework, which was commissioned as the CBBC answer to Mock the Week. The show features two teams of comedians or celebrities and a child as team leader. Stirling hosts the show of 'off-the-wall questions, nonsensical studio games, and slapstick challenges'. He was nominated for a BAFTA in 2014 for best children's presenter for his hosting of the programme for two series.
2015–present
In June 2015, Stirling became the narrator of ITV2 reality series Love Island, which entered its sixth series in 2020. In 2016, Stirling starred in the ComedyCentral seriesDrunk History. He occasionally appears as a TV & film reporter on ITV's weekend morning show Weekend. He presented CelebAbility, a six-part entertainment series for ITV2. On 22 December 2017, Stirling sat in for Chris Stark on the Scott Mills Show on BBC Radio 1. Stirling hosted Scotland's Big Night Out on 31 December 2017, as part of BBC Scotland's Hogmanay 2017. In May 2018, Stirling was the voice over for the BAFTA TV awards. In February 2019, it was announced that Stirling would be a contestant on the eighth series of Taskmaster. He also was the host of the first programme on the BBC Scotland channel, A Night at the Theatre. In April–May 2019, over six episodes, Stirling featured as one of the six comedians on the TV show Comedy Bus, in which each comedian took the others back to their home towns, Stirling took the group back to his native Edinburgh.