In 2003 and 2004, Gleeson appeared in Channel Ten's sketch comedy program, skitHOUSE. He played various characters in the sketches; most famously the Australian Fast Bowler, a parody of Dennis Lillee.
He has been seen as a regular on programs such as The Morning Show, Good News Week, The Project and Good News World. He has also made guest appearances on Sunrise, Thank God You're Here, The Sideshow, The Glass House and Rove. He has also done TV commercials for Red Rooster.
Until 2009, he was heard on Mix 101.1 in Melbourne presenting the breakfast program Mix Mornings with Brigitte Duclos. He was replaced by Lehmo in 2010.
Gleeson has appeared on The Little Dum Dum Club four times. He first appeared as a standalone guest on the fourteenth episode of the podcast. The show was published on the 24th of January, 2011. He would not return until the show's 104th episode, alongside Xavier Michelides. This was followed by an appearance at a live episode alongside Luke McGregor and Nick Cody. His most recent appearance came in episode 156, with good friend Justin Hamilton.