Since you're a connoisseur of niche entertainment, here are a few suggestions for obscure creators.
Tanith Lee, author. Neil Gaiman stole most of his best stuff from her. In Night's Master the hero is Satan, and in Death's Master, the protagonist is Death.
Ross Thomas, author. Washington reporter turned novelist, his books almost always focus on dirty politics. 'The Porkchoppers' is about a Union election back in the Nixon Era and 'Briarpatch' makes the small city it's set in a major character.
Russ Meyer, movie maker. 'Faster Pussycat! Kill! Kill!' The title of the movie is the most subtle thing in it.
There's a line in 'Tropic Thunder' where RDJ's character says he never breaks character until they record the DVD commentary. In the DVD commentary he's still doing the Fred Williamson voice.