Sherry was born in Northern Ireland before studying at the Glasgow School of Art. He is best known for his performance art. Stitching is a video of him stitching pieces of wood to his feet while he offers verbal instructions on how to do this. Other works include Carrying a bucket of water about for a week and Avoiding eye contact for one seven day period, both of which consist of the activities in their titles. Sherry has said he is trying to "expose the systematic processes of day to day life".
In 2003, Sherry was shortlisted for the Beck's Futures prize. He lives and works in Glasgow.