I’m doing the 150 pokémon for my first 150 FA watchers.

  RarewareRat
Rare, as we called him, watched me on February 28, 2013. Although there’s a lot more to him, the most consistent theme in his gallery which is not just to show what a character looks like, is those characters gaming. What game could he play that would make sense for his assigned Pokémon, Jigglypuff?
Hey You, Pikachu! was a game that flopped pretty badly both critically and commercially (if I may go on a tangent, more than the voice recognition’s shortcomings, I think the fact that kids played the Nintendo 64 mostly when they stayed home sick from school –you know when their voices probably weren’t working too well– had more to do with it). It features a rather long mission involving a Jigglypuff. It’s clear a lot of work went into this model and its animations; and the game, from the beginning, announced it had an ending; so, many people assumed that, finishing the game, would unlock a “Hey you, Jigglypuff!” mode. It was one of many rumors at the time such as the Mew Truck or, as ArisuVixen pointed out, Bill’s Garden
It’s hard to believe now, but at the time, Jigglypuff was about as popular as Pikachu thanks to the anime
Anyway, Rare gets a version of Hey You, Pikachu! where the rumors are true
^{I’ve always had trouble with Game Controllers. Here you can see how the game controller is not exactly the right size for Rare, but it doesn’t matter because he’s using the microphone attachment. The N64 itself was also a challenge. What surprisingly wasn’t, was the CRT TV.}

  TheStratovarian
I’m not entirely sure when Stratovarian watched me, but I was delighted to discover that their favorite theme is …wait for it… Pokémon! This, however, did make it hard for me to decide what to do with them and their assigned Pokémon: Wigglytuff.
When in doubt, my go-to has become to draw them in a trainer pose, but that had two problems:
One, there are actually no Wigglytuff trainers in the original game. However, there’s plenty of Jigglypuff trainers. They are all Lasses. And I don’t know Stratovarian’s gender.
And two, there are no references for Stratovarian’s character, neither the one they were using back then nor the one they’re using now
^{So, I had to improvise. The main thing was making the pose not be too girly or too manly, in case it turns out Stratovarian is staunchly male and I’ll have to correct this. The tail stripes are based on the stripes of their current character since, although the horn is gone, I doubt they’ll have changed that much. For Wigglytuff, I again wanted to do something different from last time to suggest they’re in their summer coats. The result is, not entirely accidentally, Big Chungus.}

As with the twitter sketches, if you want yours colored, or if you want me to edit you in to somebody else's, I'll happily do it for $5 (not counting shading)