Past research has been inconclusive regarding the specificity of associations between discrete pleasurable emotions and internalizing symptoms. Contentment may be especially relevant to depression, whereas tranquillity may be especially relevant to worry. The goal of the current research was to clarify the mixed findings regarding the relation between pleasure deficits and internalizing psychopathology. Participants from three samples (Total N = 757) completed alternative measures of depression and pleasurable emotions. Participants in Study 1 also completed a measure of anticipatory and consummatory pleasure, and close peers to a subset of participants (N = 64) reported their perceptions of participants' depression severity. Participants in Studies 2 and 3 also completed a measure of worry. Across the three samples, contentment was significantly negatively associated with self-reported depression. This association could not be accounted for by tranquillity, cheerfulness, anticipatory pleasure, or consummatory pleasure. Contentment was also strongly negatively associated with peer-reported depression. Contentment was more strongly associated with depression than was cheerfulness. However, the strength of the association between contentment and depression relative to the strength of the association between tranquillity and depression depended on how contentment and depression were measured. Conversely, tranquillity was more strongly associated with worry than were contentment or cheerfulness. This study provides further evidence of the potential importance of the role of contentment in depression and tranquillity in worry. It may be useful to attend to contentment when assessing and treating depression and to attend to tranquillity when assessing and treating elevated worry.