All Nine of Jon Lovitz’s ‘Simpsons’ Characters, Ranked by Smarminess

Along with Albert Brooks and the late Phil Hartman, Saturday Night Live alum Jon Lovitz was one of the great, multi-character recurring guest stars during the Golden Age of The Simpsons. But whether Lovitz was playing arrogant director Llewellyn Sinclair or ebullient art instructor Professor Lombardo, each of his animated creations were still sure to get a healthy dose of his signature smarm.

Not all smarm is created equal, though, and so some of these characters were much smarmier than others.

9 Ms. Sinclair

First Episode: “A Streetcar Named Marge,” Season 4, Episode 2

Profession: Owner of Ayn Rand School for Tots

Smarm Factor: The sister of the better known Lovitz character Llewellyn Sinclair, Ms. Sinclair actually appears somewhat genuine. She’s strict and mean and she takes away Maggie’s pacifier, but her overall smarminess is low compared to other Lovitz characters.

8 Professor Lombardo

First Episode: “Brush with Greatness,” Season 2, Episode 18

Profession: Art Teacher at Springfield Community College

Smarm Factor: He’s a grandiose art instructor who only spouts praise at his students. At first, his compliments appear to be a put on, but when he even compliments a janitor for painting a sign, it’s clear that he really is that excited about everything.

7 Himself

First Episode: “My Way or the Highway to Heaven,” Season 30, Episode 3

Profession: Actor!

Smarm Factor: Though seen only briefly, the real Jon Lovitz appears as a dead version of himself who is in heaven. He’s mentioned as being a guy who brings his dog on planes posing as a “therapy dog,” and then he insults God’s appearance. He’s plenty obnoxious, but hardly more so than most of Lovitz’s other characters.

6 Jay Sherman

First Episode: “A Star is Burns,” Season 6, Episode 18

Profession: Film Critic

Smarm Factor: Jay Sherman is a self-centered, name-dropping aristocrat who comes to Springfield to judge a film festival. He’s pretty damn smarmy, but we know from the two seasons of The Critic that he’s got a number of endearing qualities as well — for instance, being a caring boyfriend and being able to play the trumpet with his belly button.

5 Avery Devereaux

First Episode: “Homer Defined,” Season 3, Episode 4

Profession: Boss/Possible Actor

Smarm Factor: In a blink-and-you’ll-miss-it appearance during Season Three, we see Avery Devereaux on TV demanding that his beautiful blonde employee kiss him. When she refuses, he fires her and then they make out anyway. He’s a lecherous creep, but he’s most likely just an actor on a soap opera Marge is watching. Actors can be plenty smarmy, of course, but it’s unfair to judge Devereaux — or, the man playing Devereaux — on such a brief appearance. Who knows? That guy could be the Tom Hanks of the Simpsons universe.

4 Aristotle Amadopolis

First Episode: “Homer Defined,” Season 3, Episode 4

Profession: Owner of Shelbyville Nuclear Power Plant

Smarm Factor: A Greek billionaire with utter contempt for his staff, Aristotle Amadopolis is a bullying boss who has no problem humiliating his staff. As for his smarm though, he’s outdone by several other Lovitz characters.

3 Enrico Irritazio

First Episode: “Homerazzi,” Season 18, Episode 16

Profession: Paparazzo

Smarm Factor: “The World’s Greatest Celebrity Shutterbug,” Enrico Irritazio is hired by Rainier Wolfcastle to take embarrassing photos of Homer when Homer becomes a paparazzo. He’s sneaky, grandiose and believes he’s a god. Given that a paparazzo is just about the smarmiest profession on Earth, this character would likely rank higher if we saw more of him.

2 Artie Ziff

First Episode: “The Way We Was,” Season 2, Episode 12

Profession: Former Billionaire

Smarm Factor: Marge’s prom date back in high school has appeared several times on The Simpsons, and he’s always trying to figure out a new way to get Marge back. He’s about as conniving and self-centered as he can possibly be and his smarminess is only outmatched by one other Lovitz character…

1 Llewellyn Sinclair

First Episode: “A Streetcar Named Marge,” Season 4, Episode 2

Profession: Theatre Director (and, yeah, he’d definitely spell theater that way)

Smarm Factor: By his own admission, Sinclair is not an easy man to work for. When he introduces himself at the Springfield Community Theater, he brags that he’s directed three plays in his career and that he’s had three heart attacks — that’s how much he’s willing to suffer for his art. He also brags that, when he directed Hats Off to Hanukkah, he reduced more than one cast member to tears (and those were fourth graders!). Sinclair’s smarm is so strong that it bleeds right into insufferable obnoxiousness.