Globally the burden due to mental disorders is continuously increasing. Still, professional help-seeking behavior is not fully understood. To conceive cultural determinants of help-seeking is crucial to reduce personal and social costs of (untreated) mental disorders. The current study investigates mental health stigma and help-seeking attitudes in a Cuban (n = 195) and a German (n = 165) sample. In a questionnaire survey we asked for attitudes towards mental illness and professional help-seeking in the general Cuban and German populations. The cultural context was associated with mental health stigma and professional help-seeking attitudes. Interestingly, Cuban participants reported stronger mental health stigma and more willingness to seek help. In multiple hierarchical regression analyses, community attitudes towards the mentally ill significantly predicted help-seeking attitudes, especially in the Cuban sample. Only in the German sample, more negative individual beliefs about mental illness predicted more self-stigma on help-seeking. Beyond that, cultural context moderated the association between mental health stigma and help-seeking attitudes with a stronger association between the measures in the German sample. However, gender did not predict help-seeking attitudes and self-stigma on help-seeking and no interactions between community attitudes, cultural context, and gender were found in the prediction of help-seeking attitudes. Similarities and differences between the samples are discussed in the light of the cultural contexts and peculiarities of the current samples. Concluding, implications of the current findings are reviewed.