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.

Comedy Central Roast of Justin Bieber
2015
6.8/10

Chris Rock: Tamborine
2018
6.4/10

Louis C.K.: Hilarious
2010
7.8/10

Gabriel Iglesias: Hot and Fluffy
2007
7.5/10

Kevin Hart: Laugh at My Pain
2011
7.0/10

Ziegfeld Follies
1945
6.0/10

Zach Galifianakis: Live at the Purple Onion
2007
7.0/10

Pups Alone
2021
5.8/10

Accepted
2006
6.5/10

Donald Glover: Weirdo
2012
6.8/10

Bo Burnham: What.
2013
7.8/10

Monty Python Live at the Hollywood Bowl
1982
7.4/10

Katt Williams: The Pimp Chronicles Pt. 1
2006
7.0/10

Jerry Seinfeld: I'm Telling You for the Last Time
1998
7.4/10

Gabriel Iglesias: I'm Not Fat... I'm Fluffy
2009
6.9/10

Kevin Hart: I'm a Grown Little Man
2009
7.3/10

Taking Care of Business
1990
6.3/10

The Ladies Man
1961
6.3/10

Broadway Danny Rose
1984
7.1/10

Caveman
1981
6.7/10
The Cheerful Rascal
1992
0/10