The top drawing is of my parents' Shih-Tzu, Riley. The bottom is just my mind wandering on the back on an envelope. I drew Riley on some cardboard that I put in the envelope to protect its contents better.
I like to decorate envelopes, but I don't do it enough. Folks really appreciate it.
My friend Eric Thomas used to address his envelopes on the back so that he would have a seamless surface on which to draw. I kinda like the obstacle.
Somehow , I tend to draw better on paper that I know isn't likely to be kept. Maybe it's the lack of pressure to create "art". Whenever I spent much on nice watercolor paper, I would always freeze and get stiff, afraid I would disappoint the purpose of the paper. There's less risk with scrap paper. So what if you mess up, no harm in throwing it away, right? That's why I love the freedom of drawing on napkins, table cloths, envelopes & church bulletins.
Frederick Remington used to illustrate his correspondence, too. There are many of his envelopes on display at the Gene Autrey Museum in L.A.; beautiful little pen & ink drawings of cowboys and horses, sometimes w/ watercolor, too.
I doubt my envelopes will ever hang in a museum. But at least they'll be on my mom's fridge!
(Both drawings were done with Brush Pens and Prismacolor Pencil.)