The Simpsons: 15 Most Hilarious Milhouse Moments

14. Milhouse Goes Flying (Season 7, Episode 9 - Sideshow Bob's Last Gleaming)

https://youtu.be/E5Hrvza9FkM Here's a moment that went down so well with fans that it led to the creation of an episode the next season which focused on the divorce of Milhouse's parents. In this episode, Milhouse is at a fair where kids can sit in a real F-15 fighter jet. He's sat in the jet, making gunfire noises and pretending to fire missiles at the objects of his hate, shouting, "Take that, mom! Take that, dad! Send me to a psychiatrist, will you? Take that, Dr. Sally Waxler!". He starts pressing buttons on the jet's console, only to accidentally hit the eject button, sending him flying hundreds of feet into the air. This is great because it actually makes a relatively serious point about how Milhouse isn't coping very well, but masks it underneath a layer of comedy, and then of course, sending Milhouse sky high is outrageously funny.
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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.