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).

Theo Maassen: Neuk het Systeem
1995
7.0/10

Theo Maassen: Bepaalde Dingen
1994
6.8/10

The Peasants
1939
5.0/10
Six: Inside
2009
8.5/10

Teresa's Trip
2017
5.5/10

Strange Object
2020
6.0/10
Hey Qween - Holigay Special
5.4/10

Florence Fight Club
2015
7.4/10

Dune
2020
7.4/10

The Life and Death of King John
1984
7.0/10

Do Re Mi
1966
7.0/10

Souls of the Damned
2024
6.0/10

The Bonbon Factory
2012
6.0/10

Imposter Syndrome
2024
10.0/10

Der letzte Walzer
1953
5.0/10

Venalmaram
2009
9.0/10

The Feather Fairy - Two Worlds
2023
6.0/10

The Wedding Is Accused
1986
4.7/10

Horse Drawn Traffic
1896
5.0/10
Alex Ploeg: Ultimatum
2020
6.5/10