The paradox of sad-film enjoyment deals with the question of why people are able to feel entertained when watching a sad film that ends unhappily. Previous studies explored the fact that viewers, especially women and those with high empathy readiness, enjoy such films by appraising their sadness positively. This article integrates those meta-appraisals (by developing a state version of Oliver's Sad-Film Scale) with multiple appraisal processes on different situational references (media content reference, production reference, ego reference) that enable an explanation of the paradox of sad-film enjoyment. Against this background, a between-subject experiment involving 125 students was conducted to test the constitution of sadness and enjoyment in three versions of a sad-ending film. The results indicate significant differences between the three versions with respect to sadness, situational references, meta-appraisals, and enjoyment as meta-emotion. A film version that temporarily enables a “cognitive-switch” from the protagonist's perspective to the viewer's perspective is more successful in transforming sadness into enjoyment than are film versions that evoke only the protagonist's perspective. This study delivers deeper insights in processes of transforming “negative” emotions to “positive” emotions during film exposure.