In a surprising directorial choice, "Holidays of Future Passed" basically implies from the beginning that this is how the Simpsons' futures will turn out--no fortune-teller, no shaman, and no Frink device. And in an episode full of weighty reveals (who Bart and Lisa marry, what happens to many secondaries, etc), I soon realized that I thought this was a fitting future for OFF. Yes, it's a bit on the bleak side: Bart is more slovenly than Homer and Lisa is as vaguely unsatisfied as Marge has ever been, but silver linings on a dark, cynical cloud make up some of the finest Simpsons moments. So in a way, this episode rings true with the series as a whole.
Bart, Homer, and Lisa are probably the stars of the show, with each of them having significant character reveals in the episode that were implemented organically and in an entertaining way. There wasn't really anything particularly weighty in terms of characterizations or emotion, but it certainly came across as more genuine than usual. Contrasted with the fairly realistic take on the characters, the humor goes for plenty of future craziness, such as superhuman pets and talking trees. But amidst this are plenty of quick freeze-frame gags and some of the best fake-outs, reversals, and screw-the-audience jokes in recent Simpsons history (I'm partial to the powdered cookie recipe).
I enjoyed it all-around but a few niggling problems keep it from being among the best Jean episodes for me. The future concept does feel a little overdone at this point, and I might even have preferred if they just did an "aged" story with modern-day life (like what 1990 Bart would be like in 2011...then again, that's not enough time for grandkids). The storytelling was decent but it never really strove for being better than "good enough" for me, and I would've liked some sort of emotional whopper in an episode like this.
Finally--and I have to devote a paragraph to it because it's a pretty constant problem--I'm sick of these "shocker reveals" with characters. Not just in future episodes but in standard ones too. Martin Prince is suddenly gay! And apparently he wants to be a woman! Because...why not? Why have a nuanced, entertaining character (classic era Martin) when you can cram them into some broad stereotype (gay wimpy kid)? And Lisa apparently "turns gay" for a year or two as well. I mean, she's liberal, right? Having a girlfriend (or two) is right up her alley! This type of forced writing is just obnoxious and demonstrates a lack of understanding of the characters beyond basic attributes. If you want to make someone gay, do it like with Smithers or Patty, where it has a sensible consistency. But it feels like half of Springfield has had some kind of "surprising reveal" just for the sake of humor, even when it makes no sense most of the time.
That aside, good ep. I still prefer Lisa's Wedding, but this is a close 2nd for future episodes. 4/5 B+
Pretty much every regular here could do (and has done) far better reviews and critiques than Dead Homer Society.