That is an intriguing question. And you know what that means... it's time for an essay on character-based humor in the Homestar Runner body of work!
Ssemails could be like a continuation of Strong Sad's Lament, which was always great. As the one (almost) sane man in this insane world, his show could lead to a lot of humorous interactions. He's such a great character, and probably one of the best candidates for a show.
I don't see much coming from
Smemails. There isn't a lot of potential there. It might be a funny one-off joke toon, though.
Cheatmails would be pretty sweet, and so would
Pommails to a lesser extent. However, their unintelligibility makes them feel more like side characters, and a lot of their humor comes from what we don't hear.
Marzimails might be fun, but as one of the least interesting characters, I don't see a lot of potential with that.
Now,
Zemails...
those would be great. Coach Z feels like such an absurd, multifaceted character, and an email show would allow him even more creepy/depressing/rapping/bizarre moments.
Bubsmails would be pretty amazing too, but like many other characters, a lot of his humor comes from what happens offscreen. Being a paranormal investigator, selling questionable medical coverage, making quote-unquote "mistakes"... giving him a show would reveal more of this mysterious man, but in the process, perhaps ruin the mystery.
I feel like the King of Town is another character with a lot of personality, but we don't really get to see it often.
KOTmails would show us his attempts to be cool, his corrupt leadership, and lots and lots of eating. But I feel like it might get stale after a while. I mean, he's the King of Town.
In a way, it feels like the whole point of the Poopsmith is his lack of personality. He's a bit of a blank slate, which means
Psemails can do whatever they want, but on the other hand, probably wouldn't bring anything special.
As wondrous as
Homsmails may be, Homsar is such a mysterious and enigmatic character, and is best suited to short unexplained moments.
Thinking about this, I have come to two realizations:
1. A lot of these characters don't have much of a personality, only specific traits. An email show can either lead to further exploration and depth, or repetition of what we've already seen.
2. Much of the character-based humor in this show comes from unexplained/offscreen moments. A lot of these email shows would ruin the mystery and take away what makes the character so great.
In conclusion, while not all of these would make sense realistically, I want to see all of them (Strong Sad, Coach Z, and Bubs Email in particular). I hope you have enjoyed reading this as much as I enjoyed writing it. If elected class president, I can't promise you Coke in the water fountains, but I can promise a hard-worker that will make a difference. And try to get Mrs. Hardmaster fired.