In this capacity, he received wide acclaim as the principal star of the satirical cabaret Die elf Scharfrichter ("The Eleven Executioners"), launched in 1901.

[4] Wedekind became an important influence on the tradition of German satirical writing for the theatre, paving the way for the cabaret-song satirists Kurt Tucholsky, Walter Mehring, Joachim Ringelnatz and Erich Kästner among others, who after Wedekind's death would invigorate the culture of the Weimar Republic; "all bitter social critics who used direct, stinging satire as the best means of attack and wrote a large part of their always intelligible light verse to be declaimed or sung".

[5] At the age of 34, after serving a nine-month prison sentence for lèse-majesté (thanks to the publication in Simplicissimus of some of his satirical poems), Wedekind became a dramaturg (a play-reader and adapter) at the Munich Schauspielhaus.

His relationship with his wife was turbulent: Wedekind was prone to jealousy and felt pressure to maintain strenuous creative and sexual activity in order to please her.

Originally conceived as a single play, the two pieces tell a continuous story of a sexually enticing young dancer who rises in society through her relationships with wealthy men but who later falls into poverty and prostitution.

[13] Der Kammersänger ("The Court-Singer", 1899) is a one-act character study of a famous opera singer who receives a series of unwelcome guests at his hotel suite.

In Franziska (1910), the title character, a young girl, initiates a Faustian pact with the Devil, selling her soul for the knowledge of what it is like to live life as a man (reasoning that men seem to have all the advantages).

Wedekind's symbolist novella Mine-Haha, or On the Bodily Education of Young Girls (1903) was the basis for the films Innocence (2004) by Lucile Hadžihalilović and The Fine Art of Love (2005) by John Irvin.