I caved and finally put Laa on my ArtFight

As the paintings are mostly there as a gag, my lore for Doc's individual ancestors isn't fully established and some of them may not even be canon in the way they appear in the paintings, but here's what I think.

Nosramus (white hair guy) is a Fear & Hunger easter egg. If you consider him canon he would have already been alive in the year 800 making him the first recorded person in the lineage. They're just there as a funny meme but I wanted to include them due to them often striking me as disarmingly similar to Doc in the game's canon.

Mr. Basement and the Wicked Witch are the closest to how they appear in the original skits they were based on. Mr. Basement is literally Just The One From the Video and the witch is only distinct in that she lived in late 1600s New England rather than in Oz. Her personality is otherwise unchanged. I also headcanon Mr. Basement as having existed as a Regular Man in the 1800s before becoming what he is now (he'd call it his "descension" rather than ascension)

The vigilante is the most eligible to be non canon. Idk what's up with him lol. But I will say that it's likely one of Doc's recent relatives (1970-1980s) may have Done That.

The "How to cause a traffic accident" character is the true wildcard as they aren't really their own character in the original video. I like to imagine they were a decadent artist type that one day decided to start causing problems on purpose. They probably killed a husband for inheritance or something and decided to not stop there. Overall ranking pretty high among which of their ancestors were the biggest menaces

In general Doc's family is large and sprawling and their features tend to show up every few generations. Most of their ancestors/relatives have had some connection to the occult, several were an Actual Problem to polite society and at least a few of them are still alive or around in some form to this day.

Each ancestor/family member thinks their Own occult pursuit is the coolest and finds their other relatives' paths frivolous or unglamorous

View-Monster! [Doodles + lore dump]

Cinna: Mm, I dunno yet! There's nothing important going on anymore, so nothing?