My first thought reading the question for this Ask was Jessie’s original response. Jenny and Joy both seem like returning characters, but there’s actually very few times any of them make return appearances in the show. Jennys even get unique designs (especially in later seasons), though I went with the more standard design for recognizability’s sake. I had a few different ideas for how to convey the concept here, but in the end this is what I went with.
I’m slowly working my way through the long list of human Pokémon characters I’d like to draw. Officer Jenny’s an obvious one, being such an iconic part of the series, and I got to do something kind of neat with this one. After capturing a couple of Team Rocket grunts (I know the gray pants aren’t a huge giveaway, but that is who they’re meant to be), this Jenny decided to try some unique interrogation techniques while they’re locked up. Everybody wins.