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After his acting training at Westfälische Schauspielschule Bochum from 1988 to 1992, Kessler had roles at the following theaters: Schauspielhaus Bochum, Schauspiel Frankfurt, Nationaltheater Mannheim and Schauspielhaus Zürich. Since 2005 he is starring alongside Christoph Maria Herbst, Bastian Pastewka and Jürgen Tonkel in the play Männerhort at the Theater am Kurfürstendamm theater in Berlin.
2002 he had a starring role in the acclaimed film Zwei Wochen Argentinien (Two Weeks Argentina). 2003 he took part in Glückstag (Lucky Day) and Für gutes Betragen (For Good Behaviour) and Kesslers Knigge.
Since 1992 he is working for television. Beyond others he appeared in the following productions: Siebenbirken, Schwarz greift ein, Das Schicksal der Woche, Hotel Mama 1-3, Sonntags geöffnet, Der letzte Kurier, Sophie, Callboy, Kommissare Südwest, St. Angela, Ein Fall für Zwei, Großstadtrevier, Tatort, Der kleine Mönch, SK-Kölsch, Das Leben der Philosophen and SOKO-Köln.
From 1999 to 2000 Michael Kessler was cast member of Switch. From 2001 to 2002 he was part of the Wochenshow cast. Afterwards he appeared on Axel!, Urmel aus dem Eis, Ladyland and Pastewka. Beginning with the first episode in 2004 he is a regular on Schillerstraße. Additionally he took part in Genial daneben and in the "ProSieben Märchenstunde (ProSieben Fairy Tale Hour)" in the episodes Rotkäppchen (Little Red Riding Hood), Froschkönig (The Frog Prince) and Aschenputtel (Cinderella).
Since October 2006 he is driving on RBB the Berliner Nacht Taxe (Berlin Night Taxi). "I want to have the unaltered stories of the night", says Michael Kessler who loves new challenges. "We're going to meet authentic people. That's no talk theater with cast actors." The series with six episodes was first broadcast on 30 October 2006 and aired every fortnight. In 2007 and 2008 he was working on Switch Reloaded and started work on his own TV show.