This particular pun was inspired by a particular piece of artwork done by the talented Kimber Grobman, who designed a similar pose with a Pilgrim and Native American giving each other a leaping high five for a Thanksgiving project. I fell in love with the energy from the pose and decided I could utilize it for a work.
I originally drew this pair as part of 'Inktober 2015' which can be seen here and it ended up being a finished illustration for Wondercon 2016, which I used for my annoucement, and then utilized for a price sheet at future conventions. It wasn't until a later date I ended up making them available for purchase.
While the image itself was made separate from others, I did use the same color scheme from Caff-Fiend for the coffee cup character. The pun here is that both characters house caffeinated beverages that offer a 'high', and they are in essence also giving each other a 'high-five'. This easily became one of my favorites from the series. It is entirely digital, made in Illustrator, Painter, and Photoshop.
The image is available for purchase at my etsy store here as a print or on a tote bag:
High Five (Tote Bag)