"Simpson and Delilah" (October 18, 1990)

Not only the earliest gay-themed Simpsons episode we've ever done, this one is also the first gay-themed episode The Simpsons ever did. And while the enigmatic Karl doesn't get to be explicitly gay, we argue whether having a gay-coded character might have been the show's way to — in its second season and at the height of Simpsons mania — signal to grown-ups that no, despite the t-shirts, this was not a show for kids and it could operate at a higher level. But how many adults watching TV in 1990 knew who Harvey Fierstein was?

Remember when I did a supercut of all the LGBTQ jokes on The Simpsons? It still lives, even if you have to go to YouTube to watch it now for stupid homophobic reasons. It has 3.7 million views so far! I just think that's neat!

Also listen to the most recent Talking Simpsons take on this episode here.