"The Way We Was" is an important episode in defining early Simpsons canon. A majority of the episode is dedicated to a flashback story that will help cement some of the details of young Homer/Marge that will remain canon for some time, and most of the characters we'll be encountering here will reflect this era.
But the first two weeks of covering this episode have nothing to do with that.
Characters like this have a weird in between state in the fictional world of The Simpsons. This is not celebrated film critic Gene Siskel, but...also it is? He's Schrodinger's Siskel.

It's not a guest appearance (Dan is doing his voice), and he's never directly namechecked - the name of the show he's appearing on is even completely made up. But audiences of the time are expected to recognise these critics as Siskel and Ebert.

We'll encounter a few of these celebrity stand-ins throughout the show's history - including a very important one next week - and they kind of occupy a strange space where we know who they are, they know who they are, but no-one is going to literally come out and say it, presumably to avoid legal issues. It would mostly fall under parody, which does not require this level of obscuring identity, but I suppose they're just being safe.
Gene Siskel never appeared on The Simpsons directly before his death in 1999, although they poke fun at him again in season 5's "Burns's Heir":

It's all in good fun - Siskel and Ebert appeared to have a sense of humour about themselves, and voiced themselves in an episode of The Critic (created of course by Al Jean and Mike Reiss.)


This post is part of my "Every Simpsons Character Ever" series. For a list of my rules in this project, click here.