This research was conducted to gain an understanding into how singers of the Japanese-invented form of singing entertainment known as karaoke view the importance of singing ability in karaoke, and what they consider to be the respective roles of the singer and the listener. A total of 6 semi-structured interviews were conducted on 3 Japanese informants and 3 Finnish informants to form 6 separate life history case studies, which were then thematically analyzed, and common themes identified. The study found that greater self-rated singing ability of a respondent correlated with higher perceived importance of singing ability, and that a singer is expected to consider the listeners’ preferences and the mood of the occasion when deciding on which song to sing, but that lower singing ability is generally not a role conflict. It was also found that a Finnish-style karaoke bar is actually a low pressure singing environment when compared to the more intimate Japanese forms of karaoke, due to it being common and acceptable for listeners to not pay attention to the singer, while in Japanese karaoke social cohesion is higher.