Karl Is the Simpsons' First Gay Friend
From Gayest Episode Ever
"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 leve