This paper is a study of cultural failure in the case of a Philadelphia artisan and entrepreneur in the 1780's and 1790's. In analyzing cultural change between 1785 and 1850, Paul Faler and Bruce Laurie focus on the interplay between "persisting" traditional culture and "rising" industrial culture. However, the failure of traditional popular culture was also a significant dimention of cultural transformation. This paper traces the process by which John Fitch, the inventor of the steamboat, found himself incapable of representing himself through early modern languages of masculinity. After his second year of work on the steamboat project, Fitch stopped representing himself in terms of an early modern language of "independence" and "community." Instead, he began to represent first his situation, and then himself, in terms of images of captivity, torture, and execution. I argue that this shift indicated that Fitch was representing himself and his surroundings in terms of threats to his bodily integrity rather than representing himself as opposed to such threats in the traditional manner. Unable to live his cultural inheritance, Fitch groped his way to a self-representational imagery of amputating his own limbs, surrendering for execution, and letting himself be burned alive. Fifty years later, the embrace of bodily exposure as a pre-condition for individuality would be the object of extensive ritual on the part of temperance societies and fire companies. By that time, however, Fitch has long since committed suicide, unwilling to survive his borderline experience between early modern and industrial culture.