I'm not even sure where to start when talking about Kosuke Masuda's Gag Manga Biyori. All sorts of weird characters, historical figures and everything in-between experience crazy shenanigans after being pulled through a Gordian knot of the bizarre logic common to gag manga.
I'm only familiar with this manga from having seen the tiny 5-minute long episodes of the anime (directed by Akitaro Daichi of Sexy Commando fame...) but holy crap do they cram a lot of insanity into those five minutes. It's a pretty hilarious series and I would totally buy it if it was available in English.
fake edit: Couple of quick notes. GMB used to be in Shonen Jump but now it's in Jump Square. The latest season of the GMB anime has changed to full blown 1/2 hour episodes. This action figure of protagonist Shotoku Taishi looks hella rad.