I was recently asked to do an illustration for my rugby team The Saracens. Every year they hold a banquet where they give out the Willy Awards, which are t-shirts given as prizes to the individuals who manage to do the most embarrassing things throughout the season.
For the last couple of years I have done the illustrations for these shirts. They are always a depiction of Willy a non fictional Character who's antics the awards I would guess are based on.
In the past there have been pictures of Willy as an Oscar trophy, a Willy version of the Golden Boy, Also I have done versions with Willy Sticking his head between his legs and sniffing his own A$$. It is a vile looking as it sounds...Maybe more.
I missed last year but was approached to do it again this year. So this time I decided to take the approach of Willy as a 1940's Pin Up. The kind you would see on the side of a WWII Bomber.
Here are some of the sketches I did to work out positioning and the stylization of Willy.
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