This paper applies Speech Act Theory towards an investigation of the use and role of self-praise/positive self-assessment in the texts of three Chekhov’s plays: The Seagull, Three Sisters and The Cherry Orchard. The findings conducted with manual coding of texts for the speech acts of self-praise/positive self-assessment suggest that Chekhov employed self-praise for a number of textual and character-building functions. In particular, self-praise functions as a literary device to identify less likable characters as well as to provide a chance for more likable characters to stand up for themselves against injustice and provocation. The self-praise/positive self-assessment comes in mitigated and aggravated forms. Mitigation is mostly achieved through grammatical or phrasal means, as well as semantically through self-criticism, whereby the only form of aggravation observed in the data was other-criticism/other-derogation. Specific forms of a positive self-assessment likely unique to Chekhov’s plays are ‘linguistic brags’, i.e., contextually unjustifiable switches to French and Latin as well as ‘generational’ positive self-representation in Three Sisters. The results suggest that investigations of speeh acts in dramas could be productive for literary theory, as they shed more light on the characters development as well as the genre mastery of the playwright.