Although sad films elicit states of sadness and cause onlookers to mourn beloved characters, these media offerings also lead to enjoyment. This paradoxical situation challenges both theoretical approaches and empirical studies in entertainment research. Based on an appraisal-theoretical framework, the present study examined the role of multiple appraisals of recipients’ sadness. It is argued that these so-called meta-appraisals are able to transform one’s sadness into a positive meta-emotion (i.e., enjoyment); this process is called valence transformation. Results of an experimental study (N = 149) showed that in cases of a sad film ending, participants experienced higher levels of sadness than they did in cases of a happy ending. Furthermore, given a sad ending, meta-appraisal processes were activated that mediated the relationship between sadness and enjoyment. If the film had a happy ending, however, there were no indirect effects. Results are discussed in the light of theoretical considerations.