Comedy Gleeson's first stage appearance was as the character "Malcolm" (for two years) dressed in a flannelette shirt, tracksuit pants and a wig. He later went on to perform at major comedy events including the
Melbourne International Comedy Festival, Sydney Comedy Festival,
Adelaide Fringe, Brisbane Comedy Festival,
Perth Fringe World,
Edinburgh Fringe and
Montreal Comedy Festival. In December 2007, Gleeson entertained Australian troops on active duty in Iraq and Afghanistan. He wrote of this experience in his book
Playing Poker with the SAS: A comedy tour of Iraq and Afghanistan, which was published in October 2008. Three of Gleeson's stand-up shows have been nominated for the
Helpmann Award for Best Comedy Performer:
Tom On! (2007),
Up Himself (2011) and
Quality (2014). Gleeson’s stand up show
Joy (2019) won Best Comedy at
Perth Fringe World. Gleeson’s stand up show
Lighten Up (2020) also won Best Comedy at the
Adelaide Fringe.
Radio From 2004 to 2005, Gleeson presented the Sydney and Melbourne evening radio program
Tom & Subby with Subby Valentine on
Triple M. During 2009, Gleeson presented the Melbourne radio breakfast program
Mix Mornings with
Brigitte Duclos on
Mix 101.1.
Television In 2003 and 2004, Gleeson appeared in
Network Ten's comedy sketch program
skitHOUSE, playing various characters including the "Australian Fast Bowler", a superhero parodying
Dennis Lillee. In 2006, Gleeson won Australia's Brainiest Radio Star. In 2008, he was a panelist on the short-lived ''
Big Brother's Big Mouth''. In 2009, Gleeson was in the "They don't get it in Australia" advertising campaign, where he asks people in the
United States about
Red Rooster. Gleeson also made several appearances on
Good News Week between 2008 and 2011. In 2013, Gleeson co-hosted Australian comedy chat show
This Week Live with
Tommy Little,
Dave Thornton and
Meshel Laurie. In 2015, Gleeson appeared on the
ABC satirical television news program
The Weekly with Charlie Pickering, hosting the segments "This Is What You Think", "Go Away" and "Hard Chat". In 2016, he began presenting
Hard Quiz, a spin-off of his "Hard Chat" segment from
The Weekly. It has been speculated that one of Gleeson's interviews in 2017 led to
Sophie Monk getting the lead in
The Bachelorette Australia. Gleeson is the main host of the Australian version of
Taskmaster, working alongside his assistant, comedian
Tom Cashman. In 2022 he performed in a celebrity tribute to Australian comedian and actor
Paul Hogan,
Roast of Paul Hogan, which was broadcast on Australia's
Seven Network. ==Awards and nominations==