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Maassen won two of the biggest comedy contests in the Netherlands in 1990, the Groninger Studenten Cabaret Festival(GSCF), and Cameretten. The GSCF jury was not pleased with the quality of the contestants that year, and gave Maassen the first prize, remarking he was the best of the year, but still not very good. In the following years, however, Maassen fame grew steadily, especially amongst students. Maassens style was based on stand-up comedy: Alone on stage, telling jokes and stories to amuse the public, without any musical support (a thing common for most Dutch comedians up to that point). Since 2000, Maassens shows are shown on Dutch national television, making him more and more a household name.

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Louis C.K.: Hilarious

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Kevin Hart: I'm a Grown Little Man

Jim Jefferies: I Swear to God

Gabriel Iglesias: Aloha Fluffy

Rowan Atkinson Live

Kevin Hart: Laugh at My Pain

Jim Jefferies: Freedumb

Comedy Central Roast of Justin Bieber

Aziz Ansari: Buried Alive

Het Lustige Kapoentje

Hans Teeuwen: Industry of Love

Theo Maassen: Ruwe Pit

Micha Wertheim: Voor Je Het Weet
De Vliegende Panters: Ebbinge, Vrijdag en De Bekker

Heerlijk Duurt Het Langst

Rayen Panday: Fenomeen

Herman Finkers: Na De Pauze

Theo Maassen: Neuk het Systeem

Najib Amhali: Freefight
Caribbean Combo: Tijd voor Caribbean Combo

Jochem Myjer: Adem In, Adem Uit