The depiction of sin has been fundamental to European visual culture for hundreds of years, especially – but not only – in Christian art. Addressing the mutable and often ambiguous representation of sin, this book highlights its theological underpinnings, cultural afterlife, and contradictory and controversial aspects from the fourteenth to the twenty-first century. Drawing on paintings from the National Gallery and elsewhere, including pictures by Cranach, Velázquez and Hogarth, as well as modern and contemporary works by Andy Warhol, Tracey Emin and Ron Mueck, this story of sin moves freely across countries and centuries. From paintings that explicitly explore theological ideas, such as the story of Adam and Eve and its aftermath, the seven deadly sins and the Immaculate Conception, to moralising or seductive depictions of ‘sinful’ everyday behaviour, it blurs the boundaries between religious and secular art.