I mean, I didn't discover Homestar Runner until a few years after Tamers, so it's hardly surprising that I wouldn't think this at the time. And I did just go on a pretty major Strong Bad Email binge right before watching this episode, so my perspective was definitely a bit compromised...
But you see it, right? A short, big-headed loudmouth who thinks he's a lot cooler than he is? He even wears red gloves!
(Also, I definitely spent less time actually drawing this than I did debating which of Strong Bad's computers to use. MUCH internal debate was had.)