The article examines the new developments in Estonian playwriting of the 1990s and 2000s in the context of Western postdramatic theatre. Democratization of Estonian theatre system (first of all, the appearance of small privately-managed theatres as an institutional alternative to state theatres) and the abolition of Soviettime censorship created the necessary makings of artistic changes both in the field of theatre and playwriting. The changes, supported by lively exchange of influences and ideas between Estonian and Western theatre, have been rather gradual than radical. The spread of new writing practices like so-called directors' dramaturgy and collective devising of performances have given rise to substantial changes in the poetics of playtexts, based to a great extent on postdramatic aesthetics. The documentary theatre of Merle Karusoo and the post-modernist playwriting of Mati Unt are observed more closely in the article, as well as particular modes of devising performance and textual strategies, used by the Theatre NO99. The new playwriting practices, most closely intertwined with the processes of creating theatre performances, put forward a range of questions related to the definition and status of drama as a literary genre.