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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.

Chris Rock: Tamborine

Gabriel Iglesias: Hot and Fluffy

Louis C.K.: Hilarious

Kevin Hart: I'm a Grown Little Man

Comedy Central Roast of Justin Bieber

Aziz Ansari: Buried Alive

Jim Jefferies: Freedumb

Kevin Hart: Laugh at My Pain

Rowan Atkinson Live

Jim Jefferies: I Swear to God

Iliza Shlesinger: Elder Millennial

Gabriel Iglesias: Aloha Fluffy

Yora Rienstra: Eerlijk Gezegd

Het Lustige Kapoentje

Rayen Panday: Fenomeen

Pieter Derks: Van Nature

Rayen Panday: Drie keer Rayen

Hans Teeuwen: Industry of Love

Theo Maassen: Ruwe Pit

Alex Agnew: Ka-Boom!

Alex Agnew: Morimos Solamente

Louise Korthals: Alles Is Er

Wim Helsen: Heden Soup!

Theo Maassen: Zonder Pardon