The desire to personalize airplanes probably has been around from the beginnings of aviation. For instance, there was a time when military airplanes were decorated with art work by their air crews. Often, in those pre-p.c. days, these decorations were risqué and even lurid.
Sometimes the airplane name was on the blunt side:
Or with double entendres:
Still others used patriotic themes:
I wonder if these would be allowed today. I wonder also how the Generals and such felt about this; and what Mom and Pop felt about their son posing against the Strawberry Bitch.
When commercial aviation developed in the United States, the emergent airlines went for a totally uniform look, often using reds, whites, and blues. One exception was the now-defunct Braniff Airlines, which used their jet planes with individual color schemes. On one occasion, they even called on artist Alexander Calder to design a color scheme for one of their planes. This was an exceedingly first-rate creation:
However, airplane nose art reached its most surreal with a Hello Kitty-themed plane when EVA Airlines put it into service. Unfortunately, it was used only on Japan routes.