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Kessler had his acting training at the Westfälische Schauspielschule Bochum from 1988 to 1992. Afterwards he began acting roles at 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.
In 1991, he appeared in the comedy film Manta, Manta and after that he acted in numerous big screen productions like Schtonk!, Little Sharks and Nordkurve (North Stand). In 2006, he starred in Hui-Buh, Das Schlossgespenst. In 2015 he starred in Schmidts Katze.
In 2002, he had a starring role in the acclaimed film Zwei Wochen Argentinien (Two Weeks Argentina). Later in 2003, he took part in Glückstag (Lucky Day) and Für gutes Betragen (For Good Behaviour) and Kesslers Knigge.
Kessler has been working for television since 1992. Among the productions he participated are 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, Kessler was a 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. He became a regular on Schillerstraße since its first episode in 2004. Additionally he took part in the game show 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, Kessler became the driver and host of RBB Fernsehen's Berliner Nacht Taxe (Berlin Night Taxi). "I want to have the unaltered stories of the night", says himself 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 became the cast member of the Switch Reloaded and started working on his own TV show.