7. Milhouse, The Dud (Season 7, Episode 25 - Summer of 4 Ft. 2)
https://youtu.be/SHGU9HuYDDk The Simpsons visit Ned Flanders' beach home, and Bart brings Milhouse along with him. When the family are playing a Mystery Date game, one of the panels reveals a kid holding a wilted flower with blue hair and glasses, bearing an uncanny resemblance to Milhouse. Marge laughs and says, "You got the dud!", before Homer joins in and says, "Hey, he looks just like you, Poindexter!", and after Bart moans that he can't hang out with his friends, Homer says, "You got friends. You got the dud right here. Stand up for yourself, Poindexter." It's a funny moment but also telling, because it shows that even the parents of Springfield don't have a whole lot of compassion for Milhouse, and Bart doesn't even seem that bothered about him. It's slightly painful to watch as a result, but undeniably amusing.
Stay at home dad who spends as much time teaching his kids the merits of Martin Scorsese as possible (against the missus' wishes).
General video game, TV and film nut. Occasional sports fan. Full time loon.