It was for AwfulJams 2016, a game jam run by some goons over at the Something Awful Forums. It's a month long, and this year's theme was "Games for Grandpa."
Coming into it, we had this idea to do a visual-novel style game. We had an idea of the theme, but it wasn't fully announced until the start date. Very quickly we shifted from a single-encounter visual novel with 3D characters, to a 2D Long Live the Queen style game.
The story, written by Albert, was that the elderly were getting taken over by the militant-style Millenials, being forced to conform, or otherwise mysteriously disappearing. We worked in several different endings, such as Grandpa successfully conforming by passing the Millenial's test at the end, Grandpa successfully not-conforming (but still passing the test at the end), and Grandpa escaping with a certain multi-platinum singer songwriter best friend.
Check it out here: https://floteam.itch.io/grandfathered-in
Before I get into a bit of a post mortem, here is the art that I had worked on:
I drew all of the character designs, did the coloring/shading, and inked all of the game sprites, except for the linework in base grandpa, grandma Muriel, and his grandson, Jason. Albert did the linework for those.
Here are some of the pre-ink-and-color sketches. You can see some alternate designs here.
And here are the original Grandpa Horace sketches I did, when I was exploring style.