This article takes advantage of iconography's long tradition in Christianity to study "religious paintings" as a "prototype" of sublime stimuli to explore self-transcending, awe experiences among 90 viewers from different Christian backgrounds living in Greece (Orthodox) and Canada (Catholics, Orthodox, and Protestants). Religious paintings that entail concurrently the esthetic and religious strands of the sublime were used as an exemplar to magnify the complex relationship between the moral and the esthetic aspects, the negative and the positive in awe/sublime experience, across cultures and Christian backgrounds. We used the structure of self-construal (of independence, or interdependence) to explore participants' reaction to positive and negative religious themes that belong to Western and eastern painting tradition. The results underscore the impact of culture on the spectators' experiences of negative images, prompting accommodation or assimilation via self-reflection involving transcendence and moral thoughts. The experience of "being moved" was central for the Canadian groups. "Emotional symbolism" appeared more important to Greeks who, the more they feel moved, the more engage in moral reflections in front of the painful and Western-style paintings. This appears reversed for all Canadian groups who engage in emotional symbolism and moral reflection when they are less moved. It is proposed that sublime experiences may be seen as an awe response ("thin sublime") and the element of extended self-reflection (either intersubjective which rather prompts accommodation; or, subjective which rather stimulates assimilation) could turn the experience into a "thick sublime" transcending experience.