Ostermeier began his theatrical career in 1990 acting under director Einar Schleef, one of his major inspirations, in his Faust project at Berlin's Hochschule für Künste.
After the Faust project concluded in 1991, Ostermeier began studying directing at the Ernst Busch Academy of Dramatic Arts in Berlin where in 1992 he met his mentor Manfred Karge.
He rebelled against this aesthetic, embracing the “intimate and violent” psychological realism emerging among young British playwrights like Sarah Kane and Mark Ravenhill.
[1] The 1998 production of Ravenhill's Shopping and Fucking won Ostermeier international attention and an invitation to the Berliner Theatertreffen as well as recognition as the enfant terrible of German theatre.
His realist aesthetic is indicative of his own left wing political beliefs, which starkly criticize Western capitalism and the values of modern European society.
This new approach to classical pieces was applied to Hedda Gabler (2006) – winner of both the Nestroy and Politika prize at the Belgrade International Theatre Festival as well as audience award at Theatergemeinde Berlin – and numerous other plays, including 2008's production of William Shakespeare's Hamlet, gaining Ostermeier international recognition as one of German's leading young directors.
Additionally, these interpretations of classics focused his aesthetic specifically on to the theme of the loss of utopia, while maintaining the intimacy and violence present in his earlier works.
Known for making outlandish statements about the older generation of German theatre directors, Ostermeier found himself in trouble at Wien Festwochen in 2001.