How Sideshow Bob Became a Disney Villain
The Simpsons producer Al Jean breaks down the latest Disney+ short, his favorite Sideshow Bob moments, and more.
What do Loki, Jafar, and Sideshow Bob have in common? They’re all technically Disney villains.
In a new The Simpsons short streaming now on Disney+, the frequently foiled criminal (voiced by Kelsey Grammar) sings a Halloween-themed version of “It's the Most Wonderful Time of the Year” while surrounded by a crew of classic Disney antagonists. But it’s not until I pose the question in an interview that long-time Simpsons writer and producer Al Jean realizes Sideshow Bob’s new status.
“Oh, I didn't even think of that,” Jean tells Inverse. “That's a great honor for Bob.”
Al Jean served as The Simpsons showrunner for Seasons 3 and 4, and then again from Season 13 until Season 33. He’s responsible for some of the show’s most iconic episodes (and also a lot of the less memorable seasons). Speaking to Inverse, he reveals why this Disney+ short may mark the final use of a classic Simpsons joke (Sideshow Bob’s rake gag) and the Disney brand he wants to spoof next (it’s Pixar).
This interview has been edited for brevity and clarity.
Sideshow Bob with his arch-nemesis: Bart Simpsons.
Hi, Al! It’s a real honor to interview you. I watched the new short and I wanted to ask about Sideshow Bob because he’s the star of this video. So to start, why did you decide to make Sideshow Bob the focus of this Halloween short?
Well, with these shorts, we always want to do something really different every time and special and Kelsey's the best and we have had the greatest relationship having him on the show. He's always there for us. He's always really nice and he loves to sing, which is one of the reasons he was cast as Bob by Sam Simon because he's got a great voice. So we thought him doing a Halloween version of “The Most Wonderful Time of the Year” would be great.
The short also brings back a classic Simpsons gag: Sideshow Bob stepping on rake. It actually happens a few times. Was there any debate over whether to include that joke?
I love the joke. [Director] David Silverman wanted to put it at the end and have Bob say, “Tired gag.” So to me, the point of the gag was that we kept repeating it, but that's the last time I'll do it.
Oh really? That's it? No more Sideshow Bob rakes?
I mean I can't tell anybody else not to, but I’ve finally had my fill.
Sideshow Bob vs. his other arch-nemesis: a rake.
What's your favorite sideshow Bob episode? There's so many good ones.
I guess I have a soft spot, speaking of the rake, for “Cape Fear.” I remember that was sort of a transition episode that Mike Reiss and I produced right before David Mirkin took over and I was editing it and everybody had left. That's one reason the rake sequence got so long is the show was short. We had no writers. So I just thought, Oh, okay, I can add a little time here. And then it was still a little short. It wasn't just unconscious. Sam Simon had always said: If you do a joke and it's funny and then you repeat it and it's not funny, but then you keep coming back to it, it gets really funny. So that was the principle.
That's amazing. I mean, that's a great episode and it's interesting, it connects to this new show because that one ends with him singing an entire musical. He's always kind of been this musical character.
When Sam first called him (Sam had worked on Cheers), he said, “Do you want to do this character who sings?” He said, “Yes, I do.” And we've had him sing pretty much every time he's been on.
Sideshow Bob performs the entire musical H.M.S. Pinafore in “Cape Fear.”
You’ve done a bunch of these Disney+ shorts by now. Are there any other Disney franchises that you want to do a parody of in the future?
We want to make these very special, but we keep trying. We have one that we're working on now, but I won't say what it is.
I was thinking it'd be fun to do one about for the Alien movies.
Oh, that's really cool. Yeah, no, there's so many things. Then there's stuff like Pixar. I love Pixar. Inside Out 2 was my favorite movie this year. Although they kind of do comedy animation, so it's not quite as satirical. But they've been great. Everybody's been great about using their characters, putting them in shorts.
Loki with Lisa/Thor
That'd be great cool. So a recent Simpsons episode that featured a fake series finale, which I thought was really interesting.
It was definitely a fake yes.
Yeah, it was actually a season premiere, right?
God forbid we made it the last episode of the year and people took it seriously. That was a great idea by Jessica Conrad who wrote that.
Do you ever think about actually ending the show?
Everybody's thought about it. I had an idea about 10 years ago where if we ended, the final episode would go back to the Christmas pageant that opened the first episode. So the whole series is an unbroken loop. But there is no talk about doing a final episode or ending the show at this point. I mean, I think the shows are great. Disney+ has been a huge plus for us. That episode was a way of forestalling that question. There is no actual end in sight.
Bart finally turns 11 in The Simpsons’ fake series finale.
You also made The Critic, which I love. And also I love that crossover episode with The Simpsons, “A Star Is Burns,” it’s one of my favorite episodes of the show. Is there a world where the critic comes back or we get another crossover?
It's been talked about. It's a really sort of obscure issue that it has, which is it wasn't a Fox show, so it's not owned by Disney now, either. It's owned by Sony. Jon Lovett would be happy to do it and I would love to see it come back. But it's more difficult. These other shows like Futurama, Bob’s Burgers, Family Guy, they’re doing fantastic on Disney Plus and Hulu. So I would love The Critic to somehow come to them, but it's not owned by Disney. Maybe Disney will buy it.
Home Simpson and Jay Sherman in the crossover episode “A Star Is Burns.”
Alright, I only have time for one more question here. I was looking at Season 13 of The Simpsons, which is when you came back as showrunner, and one of my favorite episodes from that season is the one where Lisa becomes a Buddhist, “She of Little Faith.” Why did you decide to tackle religion in that episode and what you think it did, right?
Well, it was funny, earlier in Season 4, I was trying to think of an idea for an episode and I said,, “Well, we've done thou shall not steal, so we should do the Sabbath episode,” which was the “Homer the Heretic,” which George Meyer wrote. So here I was going, “Well, ‘Lisa the Vegetarian’ was a great episode. What's another really interesting thing she could do philosophically that would be a challenge to Marge, too?” And that's why we had her become a Buddhist. And Richard Gere was in it, who's very Buddhist. What's great is, Buddhism welcomes all faith. So it really has an important message and a spirit tolerance.
