Dean of Students Ed Rooney is an embattled, middle-aged man on a mission: to take Ferris Bueller down a peg or two. Or twenty.
Pop Goes the Weasel
We're just going to say it: Rooney's kind of a scumball. After he discovers it's not Ferris on the phone pretending to be Sloane's dad, he sucks up to "Mr. Peterson" like a thirsty gerbil at a water bottle. Then he does the same to Sloane herself as he personally escorts her out of school. "Once again, let me tell you how deeply saddened I am by your loss," he oozes:
ROONEY: I had a grandmother once. Two, actually. Man that is born a woman hath but a short time to live and is full of misery. He cometh up, and is cut down like a flower. He flee-eth, as if it were a shadow and never continue-eth in one stay.
Flee-eth? Continue-eth? Those aren't even words. Rooney's not only a weasel, but he's completely transparent. As Rooney continues spitting his half-baked condolences at Sloane, she just rolls her eyes.
He's also bitter and frustrated. It's not difficult to see why: Ferris has repeatedly thwarted his authority and made it more difficult for him to do his job. "He makes you look like an ass," Grace tells him, not to put too fine a point on it. And when Rooney suspects that Ferris, Cameron, and Sloane are up to something, he's totally right. The problem is, Rooney's slime factor makes him a wholly unsympathetic character.
Just Another Long-Winded Villain
It's impossible to root for Rooney. He takes out his frustrations on his hapless secretary, and he's a jerk about pretty much everything. When he thinks he's nabbed Ferris at the pizza parlor, for example, he doesn't just apprehend him, he opts to speak French. That's why you don't feel bad for him—not even a little bit—when he takes a soda to the face.
Rooney's gloating backfires on him at the end of the film, too. When he catches Ferris sneaking back into the house, he has to wallow in it. "Looking for this?" he asks, dangling the missing house key in front of Ferris's face and smirking. "I gotcha, Ferris. I have dreamed about this, and this time, you little bastard, I've got you right where I want you." Then he lays into Ferris, asking the teen how he'd like another year of high school under Rooney's close personal supervision.
This is a classic villain mistake, Shmooper. From Loki to Khan to Count Rugen, bad guys just can't help but launch into an egotistical monologue before they take down the opposition. When Rooney starts explaining his plans to Ferris and drawing things out, it gives Jeanie just enough time to swoop in and save the day. And when she chucks his wallet out into the yard, we feel zero compassion. Ferris may be breaking the rules and conning everyone he comes within ten feet of, but Rooney's smarmy, bigheaded ways make him the bad guy.
The Dean of Bungles
Maybe we're being too hard on Rooney. Probably not, but maybe. Even if we are, though, the fact remains that Rooney takes things way too far. The most outstanding example of this is that he trespasses in Ferris's house. There's also the fact that he drops a flowerpot on the family dog's head, knocking it unconscious. When's the last time your school's dean of students left school, went to a truant student's house, bludgeoned the family pet, and snuck into their kitchen? Yep, that's what we thought.
Rooney has an unhealthy obsession with Ferris. He really wants to see Ferris get his comeuppance, and he's prepared to abuse his position in order to make that happen. Why? In part because he's jealous. Ferris is beloved by the entire school—from the kid taking up a collection to buy him a new kidney, to the English department that sends flowers to his house. Rooney, on the other hand, is a joke. Ferris has power and influence; Rooney is a blundering, ineffectual mess.
Rooney Eats It
To be blunt, Rooney is a stupid authority figure. All of the adults in the film are. Ferris and his friends repeatedly outwit them—or, if the adults aren't being conned, they're portrayed as boring. But if Rooney can capture Ferris, he can put the adults back in power, and maybe even restore some of their dignity.
And by the end of the movie, Rooney needs his dignity restored. The dean of students is hoisted on a clothesline of humiliation for the entire film. He bumbles through those awkward condolences to Sloane. He loses a shoe in the mud. He gets attacked by a garden hose and a dog. He breaks into a student's home. Another student kicks him in the face. His car gets towed, and he has to ride the bus home—a bus with "Rooney Eats It" scribbled on it.
Oh, and he catches Ferris, but lets him slip away because he takes too long reveling in his awesomeness. Rooney's portrayal as an unhinged doofus of minimal authority means that when he endures each one of these degradations, viewers don't feel empathy—instead they laugh at him. His obsessed, over-the-top actions earn him that pocket of warm gummy bears at the end of the film.