I wanted to draw a vintage cartoon of Richie Rich, when I realized I never liked that comic to begin with. I think it has to do with the over exaggerated lines, round curves and a too comical look (very similar to the original Casper the Ghost, because they were both made by the same illustrator). To be honest that cartoon is old (1953) nonetheless I tried some faces and a full pose from a reference drawing of Richie Rich, but could not feel any click with that.
Next up was an idea to try a caricature from a rich person such as Bill Gates or Mark Zuckerberg, but I am kind of rusty in that area. I settled with Rich Uncle Pennybags, our Monopoly Man and tried to model him to my style. Although I could have cartoonified him more, I am not unhappy about the end result.
I tried to stay true to the static pose he is portrayed in, but kept it loose. He is drawn in my Moleskine, using a 0.2 Micron for small arching and lines and a Sakura Brush pen for the more playful strokes and large black areas of his clothing.