0377 - Artie Ziff

A double-whammy of significant appearances here - not only is Artie Ziff a notable character with multiple episodes, but this is the first time Jon Lovitz voices a Simpsons character!

Were it not for Rainier Wolfcastle's brief cameo at the start of the episode, Ziff would be the most important addition to the Simpsons canon from "The Way We Was". It's easy to dismiss him because most of his appearances are after the "golden era" of the show, but by my count he has a speaking role in seven episodes - more than a lot of other beloved and memorable characters - and is briefly referenced in a few others. Unlike a lot of characters, most of his episodes actually centre around him in some way too.

His only other appearance in the first ten seasons is in season 4's "The Front", where he is not fully established beyond his "The Way We Was" details, and so he looks slightly different and is voiced by Castellaneta instead of Lovitz (for the first and only time.)

But in future episodes such as "Half-Decent Proposal" (season 13) and "The Ziff Who Came To Dinner" (season 15), we see what happened to Ziff after high-school, where he builds and eventually loses his software company, Ziffcorp, and still pines for Marge. This in turn leads to a strange twist in season 31's "Hail To The Teeth" (his most recent appearance to date,) in which he builds a fleet of Marge robots to make Marge believe they were meant to be together. It's a tale as old as time.

Ziff is a recognisable character, but I doubt he's anyone's favourite character. He's slimy and scheming and attempts to sexually assault Marge the first time we meet him. But he's a useful story tool to have for some of these later episodes, and Lovitz performs the part well - this is his most repeated character.

Incidentally, I chose to draw him as he appears in "The Way We Was", as I assume that's how most people picture him. He appears more as an adult through the rest of the show, but if Artie has a "classic" design it's his afroed teenage self. I'll probably cover his other appearances as we get to them - like I said, he next appears in season 4, so we will get to that...eventually.

This post is part of my "Every Simpsons Character Ever" series. For a list of my rules in this project, click here.