Even after catching it on broadcast TV, well over twenty years ago, the plot & that ending still are easy to recall.

Sometimes, it's nice to be reminded that something existed & that someone else encountered it, too.

I assumed Jack Black was dressed up as Gerard Way from My Chemical Romance in the reggae song (udging only by pictures of the group).
I'm hoping Ashley makes it to another season, too, but I also remember how much of a shoe-in Chloe Troast seemed to be, last season.

I like that your take on the episode doesn't seem to fall into either of the love/hate camps with Gillis.
My overall impression was that the show decided to cash in on the goodwill from the anniversary special or to set the bar low for Lady Gaga, next week.
Thanks for the review!

My guess would be Steve Ditko.
He put out a lot of work through Charleston.