In 2002, he had a starring role in the acclaimed film Zwei Wochen Argentinien ("Two Weeks in Argentina"). Later in 2003, he took part in Glückstag ("Lucky Day") and Für gutes Betragen ("For Good Behaviour").
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 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", he stated. "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.
Voice acting
Kessler has had a couple of voice acting roles. These are Rattlesnake Jake in Rango and Hackus in The Smurfs 2.