Oliver was first introduced to the theatre in 2007 with his first show 'Alice Through the Looking Glass' presented by ChildplayersACT. Oliver has since acted in 5 more productions with Childplayers where he has taken on major roles such as; Mike Teevee in Charlie and the Chocolate Factory, Baloo in The Jungle Book, Peter in The Lion, the Witch and the Wardrobe and most recently he played the Scarecrow in The Marvellous Land of Oz. 

Oliver's most recent triumph would be winning Fast+Fresh 2013 with a team composed of Childplayers. The team walked away with 'Best Directors' and 'Best overall production'.