The wide-spread adoption of representation learning technologies in clinical decision making strongly emphasizes the need for characterizing model reliability and enabling rigorous introspection of model behavior. While the former need is often addressed by incorporating uncertainty quantification strategies, the latter challenge is addressed using a broad class of interpretability techniques. In this paper, we argue that these two objectives are not necessarily disparate and propose to utilize prediction calibration to meet both objectives. More specifically, our approach is comprised of a calibration-driven learning method, which is also used to design an interpretability technique based on counterfactual reasoning. Furthermore, we introduce \textit{reliability plots}, a holistic evaluation mechanism for model reliability. Using a lesion classification problem with dermoscopy images, we demonstrate the effectiveness of our approach and infer interesting insights about the model behavior.