Cool project!! :3 We have two "family portraits" that I think fit the bill: drawings our best friends of 15 years (Supernova, for credit; shared with their permission) made of both their and our (known at the time) guys hanging out all together!! The first one isn't dated but based on who's there vs not it was probably made sometime in late 2018, the second one was June 30th 2019. Here's a PDF containing both drawings, let us know if you need another format or anything else!!