Callinan has performed in many mediums, including TV, film, radio and live stand-up. In 2006, Callinan presented a live comedy show as part of the Melbourne Comedy Festival about his fertility problems entitled Damian Callinan has Spaznuts. That year he also debuted Babysitting, casting himself as a babysitter caring for a giant baby. In his show Sportsman's Night, Callinan, with no props, performed every role in a story about a football club gathering. He's also performed several other solo comedy shows: Damian Callinan Calls "Last Drinks", Eureka Stocktake,The Cave To The Rave: The Story of Dance and Speech Night. In 2007, he appeared in a stage show called The Complete Works of William Shakespeare Abridged alongside Frank Woodley and Keith Adams. In 2008, he played Pete Minotti in the City Homicides "Somersaulting Dogs". Callinan appeared in the 2013 film Backyard Ashes, directed by Mark Grentell. Callinan's show The Merger was commissioned by Regional Arts Victoria and Vic Health to deal with issues of racism in regional communities. Callinan began performing the show in 2010. The show tells the story of a struggling country football club that recruits newly arrived refugees to fill its playing roster. In 2015, Callinan began writing a screenplay adaption of The Merger, funded by two grants from Screen NSW. In March 2015 Callinan took his show The Lost WWI Diary to the Adelaide Fringe Festival. The show, a black humour comedy based on a diary discovered in a Warrnambool op-shop, featured characterisations of ANZAC soldiers at the time of the Gallipoli Campaign. A Fairfax Media reviewer who saw the show in Sydney in 2014, Craig Platt, noted the show managed to be both irreverent and reverent, but suggested it could have taken more risks to bring something new to the Gallipoli story. News Corp Australia reviewer Nick Richardson was impressed by the show's realism. Callinan launched his twelfth solo show, Swing Man at the Melbourne International Comedy Festival in 2016. A Herald Sun reviewer who saw the show in March 2016, James Wigney, wrote that the show was an affectionate insight into Callinan's Catholic country childhood and the world of swing dance. In 2017 the one man stage show titled The Merger received funding from Screen NSW Australia and Backyard Ashes director Mark Grentell reteamed with Callinan to helm the film The Merger which is being released nationally around Australia in 2018.
