Marge Simpson makes a promise here to a guy going to jail. She doesn’t keep it, but let’s face it, Marge has been burned by guys she met in prison before.
Lisa is getting an award: student of the millennium. Sure, the millennium is a bit new, but still. Lisa being honored is a big deal, and Marge wants one thing: she wants Homer to be there. He’s missed so many things of the children’s in the past, like picking Bart up at the airport, or taking Lisa to a father-daughter dance. After some negotiations for how drunk Homer can be, he agrees with Marge to go. In fact, Homer gets up super early and gets to the school with Maggie for Lisa’s award a full hour and 50 minutes early.
But then Marge misses it. Why? She was at the bank, and the line just wasn’t moving. She makes a quiet joke with a bug-eyed man standing in front of her, one Dwight David Doodlehopper. He seems friendly. Sure, the bug-eyed thing is kinda creepy, since it makes him look like a carton caricature of one-time Simpsons guest star Steve Buscemi…wait, it is Steve Buscemi? As someone else? Huh.
Oh, wait, Dwight and a hapless partner are there to rob the bank. The hapless partner proves to be truly hapless and makes a run for it, leaving Marge and a few other folks there to be held as hostages. The cops outside see the partner run and Lou points out the crime in numeric code, then says it’s armed robbery with a gun. Wiggum eventually figures it out as a stealy-shooty. Homer eventually shows up, though his advice of Marge not following any instructions from the hostage-taker, panicking, and trying to be a hero, sounds like the opposite of good advice. Marge does get Dwight to surrender, but she has to promise to visit him in prison.
Marge clearly is not comfortable with that.
So, you know, she doesn’t visit.
Why should this matter to Dwight? Well, he’s lonely. No one’s ever cared. His mom abandoned him at an amusement park. Meanwhile, even Snake gets visitors from his girlfriend Gloria (returning guest star Julia Louis-Dreyfus). The best Dwight can hope for is robocalls from guest star Ted Nugent urging people to vote against a ballot initiative that would ban crossbows in schools. Hey, what else are you going to use in the event of an elk attack?
At any rate, Dwight escapes from the prison out the sewer. He just missed the pipe that let the natural spring water flow out. Dwight’s luck sucks. He does catch a break because he lets it be known he only wants something from Marge, after which he will return to prison. The cops figure that’s good enough. Dwight then follows Marge around, though the closest encounter in the department store changing room turns out to be Moe.
That’s when Dwight carjacks Marge to get what he wants. What does he want? He wants a nice day at that amusement park where his mom abandoned him.
Hey, Marge actually does well there, and she felt bad about not visiting. If Wiggum hadn’t tried to arrest Dwight to prove to Lou he was better than a toy monkey at policing, it might have gone better, but Dwight had to step in to save Wiggum, and then he went back to jail.
Marge did visit after that, even if the man’s bug-eyes still disturbed, oh, everybody.