In 2013, his fourth solo show was 'Edinburgh Comedy Award Winner', in which he gave each audience member a £1 bet on him winning the Edinburgh Comedy Award. In 2013, Cassidy talked about 'Free Pound' and 'Edinburgh Comedy Award Winner' in a feature Tuesday night interview with Phil Williams on BBC Radio 5 Live, in which he said that how his grandfather saved all his life and then was unable to spend the money he had saved had inspired shows where he was now giving money away. Cassidy became the 10/1 Ladbrokes favourite for the Edinburgh Comedy Award in 2013 – after starting at 50/1, Ladbrokes dropped the odds first to 20/1 at the Brighton Fringe (as featured by The Argus) then to 10/1 during the Fringe in August 2013.