Earlier quoted context omitted.
Those were fun gimmicks and all, but Homestar Runner worked because of the cute character designs, funny writing, and Matt's genuinely outstanding voice acting. It holds up just fine on YouTube. It was more about Flash being a really powerful tool for amateur animators, and coming at a time when you didn't have much else in the way of video on the internet.
Yeah, but there was a reason that we "didn't have much else in the way of video on the internet" at the time — bitmapped videos were far too bandwidth-intensive for most people to download in realtime . (You could still download them, and people sometimes did; but a 3-minute, 240p MPEG1/RealPlayer clip was something you'd need to dedicate a half-hour to fetching, either using a download manager or Limewire. It was no…
Very little could handle buffering videos that well, or at scale.
Since people kept computers longer, and I was involved in online education/training delivery online in those years, flash video provided more backwards compatibility in a decade where IE4 wouldn't die, then IE6 wouldn't die.
Flash Media Server too, did some pretty interesting things. There were open source options like Red5 that were worth trying out.