Vladimir Kosmachevsky graduated from Pyotr Fomenko's class as RUTI/GITIS in 1988.
Beginning in the late 1980s, he staged various productions at the the Playwright Theatre in Moscow, and at regional drama theatres in Vladimir and Ivanovo. In the early 1990s he participated in the Creative Workshops founded in 1987 by the Russian Theatre Union as an alternative space for young directors (working alonside Klim, Alexander Ponomaryov, Vladimir Mirzoev, Valery Sarkisov and others). In the Workshops, Kosmachevsky invented 33 “models” for a play (Expanded Play Model No... ); an open performance based on Jean Anouilh's The Basement , designed by Yuri Kharikov); and three versions of Paul Claudel's The Satin Slipper (1993).
Throughout the 1990s, he worked in the theatres of Tilsit, Arkhangelsk, and Penza; while collaborating with the Belgian New Port theatre, and the Aparte Theatre in Moscow (in the Gaining Perspective laboratory).
In 2005 he declared his retirement from the profession of directing, and until 2010 taught acting and directing at the Moscow State Institute of Culture.