Im interested in the provenance, is it because their pasty white, red headed CEO resembles and behaves like a clown?

No it's because lots of stuff is duct taped together and then you have tons of scripts or tooling that was someone's weekend project (to make their oncall burden easier) that they shared around. Usually there'll be a flag like --clowntown or --clowny-xyz when it's obvious to all parties involved that it's destined to destroy everything one day but YOLO (also a common one).