The contemporary landscape is rife with ruins, from circumscribed tourist attractions to urban decay and demolition sites. When examined, our aesthetic experience of these sites ranges from historical distancing to the sublime and, when found in our local communities (e.g., Providence, RI), to discomfort, displacement, and horror. In particular, this paper is interested in how certain forms of demolition, from slow and messy to explosively dramatic, can be understood as compressed and heightened experiences of the traditional sublime ruin. Additionally, as contemporary artists often use the vernacular of the ruin in their work, this paper considers how three artists, Gordon Matta-Clark, Rachel Whiteread, and Robert Polidori, utilize established aesthetic categories of the ruin and destruction to create meaning and emotional power in their art