Simon Klein graduated from the Slade School of Art in 1982 and went on to receive an MA in Contemporary Fine Art Practice at Kingston University in 1997, where Klein is currently an Associate Lecturer. Klein first exhibited his work in a two-person show with fellow artist Simon Howell at Bloomsbury Gallery in 1984. Klein has since exhibited his work across the U.K., with solo exhibitions at The National Theatre, London and St Hilda's College, Oxford. Following Ruth Borchard Collection's acquisition of Klein's self-portrait in 2017, Klein's works were shortlisted for both the Chaiya Art Awards and the Royal Institute of Painters in Watercolours in 2018.
Klein is best known for his works in oil. Klein classes his figurative oil paintings as a kind of 'anti-porn', in which he depicts figures in either humorously sensual poses or in the act of searching. Klein's Self-Portrait with Cherubs (2015) reflects this theme of searching, turning the search inwards as Klein gazes into a mirror, in the act of self-depiction. Klein's most recent work has explored everyday domestic scenes in the era of coronavirus-induced lockdowns, in his own words 'chisel[ing] out a dark poetry' of 'languid shapes.' Most recently, Klein has created stop motion drawn animations for his debut single with Gare du Nord Records, entitled Cat, released in May 2020.