This article discusses the representation of woman in Estonian punch-lined jokes. After brief introduction to the problems and approaches of this field the author presents the results of the extensive research, which consisted of the survey of 1869 jokes. Jokes representing female characters had to contain one of the four most neutral keywords: woman, mother, wife and maiden (young woman in Estonian). These jokes were collected from the Internet and stem from the years 1960–2010 and are categorised using the program QDA-miner, which enables both quantitative and qualitative methods. However, the main emphasis in the approach is on the critical interpretation of the results. The jokes were divided into 4 major subcategories: 1) location of the joke; 2) the interaction partners of woman; 3) sexual content; 4) the role of the woman (active, submissive, neutral). The most frequent location for the joke was homely environment. Woman interacted in the jokes mostly with her husband, children and other family members. Surprisingly, only 27% of the material contained any kind of sex-related circumstances. The fourth and most ambiguous (open to interpretation) category was the role of the woman. It was also the focal point of my critical approach. The results show generally, that the picture of woman in Estonian jokes is rather passive and one-sided. In literally half of the jokes, woman had merely episodical role. Woman was clearly the target of the joke in 32% of the jokes and active protagonist in the rest 18%. Although it seems, that the female character had often something meaningful to say in jokes, closer look reveals that it was not the case. Even in the jokes where the woman was active, her role was still very stereotypical and reflected rather the point of view of men telling the jokes or the construction of male identity in general. These tendencies show, that the representation of woman in estonian joke material is quite static throughout the period of 1960s until the first decade of the 21st century. I maintain, that this phenomenon cannot be explained with the simple persistence of sexism and misogyny in society. One other way of explaining it, is that the inherent stability of the genre of punch-lined joke does not let new discourses appear in it. Researchers should look for other new humorous genres for more critical and complex representation of gender and femininity.