5. Milhouse Tries Baseball (Season 14, Episode 16 - Scuse Me While I Miss the Sky)
https://youtu.be/PKjcswbe23Y Declan Desmond (Eric Idle) shows up at Springfield Elementary School to make a documentary on the students' lives, and in the episode's greatest moment, he reveals a montage of Milhouse's attempts to play baseball. He says "I'll be batting 352 in the majors!" and then shows off his "skills", missing the ball numerous times, knocking out the umpire with his bat, accidentally hurling his bat, getting knocked out by the ball, and after finally hitting it, tripping over the stump, his glasses falling off. Demsond then walks into frame, asking the cameraman, "Did you get that, Simon? Brilliant! Right, let's go to Moe's", as Milhouse's unconscious body twitches and the episode comes to an end. Poor Milhouse, but his misery is so funny.