Bill Oakley on 5% Asks, ‘Predictions,’ and Room Morale
The 5% ask that changes careers.
I just sat down with Bill Oakley.
Former Simpsons showrunner, multi‑Emmy writer, and Steamed Hams creator turned food enthusiast.
In this episode you’ll learn
An ask‑playbook that beats 95% rejection and lands dream rooms (05:39).
Room rules that ship: morale > hours, pitch alternatives, protect vibe (11:22–18:56).
Why “Simpsons predictions” happen and how to use the pattern for trend‑spotting (19:34–33:06).
We dive into the details later in the conversation.
Timestamps
00:00 Intro
02:28 The Journey to The Simpsons
05:39 Asking for Opportunities
08:15 Navigating Hollywood’s Challenges
11:22 The Writer’s Room Dynamics
14:02 Maintaining Morale in Creative Spaces
16:38 The Evolution of The Simpsons
19:34 Cultural Commentary and Predictions
22:02 The Steamed Hams Phenomenon
24:47 Transitioning to Food Enthusiasm
27:46 The State of Fast Food Innovation
30:26 The Steamy Awards Explained
33:04 Philosophical Reflections on Creativity
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Here’s the full transcript:
Metwally — That One Time Podcast (00:00.11)
Simpsons was our first job in like real serious TV. It was like being hired at Saturday Night Live in 1978. Nobody was giving us any notes. Nobody was telling us what to do. And we knew it was the best TV comedy of all time. Eventually you ran the show in what was some of its best years. Cartoons and writers? Eh, sort of. That would have been so illegal, so not permitted today. How did you ultimately decide who should shoot Mr. Josh and I wanted it to be Barney.
I’d love to get your thoughts on the Simpsons ability to predict the future. Part of writing comedy is what’s the stupidest possible thing that can happen. The stupidest thing happens very frequently these days. Welcome to That One Time with Adam Metwally, the podcast bridging the gap between health, hustle and happiness. I’m with Bill Oakley, best known.
as the showrunner and multi Emmy award winning writer of The Simpsons during the acclaimed seasons seven and eight and now turned food blogger with his fans calling him the Gordon Ramsay of fast food. Bill, welcome. Thank you. It’s a pleasure to be here. Thanks for coming on. So take us back. You almost left comedy for the Foreign Service before taking on The Simpsons. What kept you writing instead of playing it safe?
The fact that it was so hard to get into the Foreign Service, that was, just a little context here, when my partner Josh Weinstein and I moved to Los Angeles, we were unemployed for about a year. we had a spec script, a spec script is what you use to try to get a job. It’s a sample script you’ve written of an episode, a show that already exists. You show you write a show you can write a TV comedy, right? So we had a spec script that wasn’t very good. And we had not gotten any jobs and our unemployment was gonna run out. And so I was like, okay, well, it’s time to consider another career.
So I sent away for the Foreign Service Exam for the State Department and it was so hard. I thought it was going to be really easy, but it was actually very, very hard. And that was when I called Josh and I like, we should write another script at that point. And because we got some good advice, we chose a show that we really liked rather than a show that we didn’t really care that much about. And the show happened to be Seinfeld and we wrote one of the first spec scripts, I think in existence.
Metwally — That One Time Podcast (02:16.258)
for Seinfeld after it only been on for a few episodes and it ended up opening all these doors, getting us these job interviews, eventually getting us hired on The Simpsons. So what lessons did you take from that experience? That think it’s always worth, I would tell you the experience that is more, that is even more germane to that, which is The Simpsons gave us an episode to write a script, which was the episode Marge Gets a Job. Conan had made that story up, we wrote it, we turned it in, they liked it, and that was kind of the last we heard of it. In the meantime, we had gotten another job.
Our Spectra has gotten us hired on a very prestigious new show. But it was show, it was a romantic comedy. And Josh and I were like, I don’t know how good we’re gonna be at writing romantic comedies. That’s not really our style. And we called our agent and said, would you please just call, please just call The Simpsons and ask if they would ever hire us. And he did, and they did. It was amazing. That’s like, can’t possibly stress.
that enough. That’s the one thing I’ve learned is like, you’ve got to ask no matter how crazy the ask is. Like that, our entire career would have been completely different if we hadn’t had to make that one phone call because what happened is it was perfectly timed because two guys had just left. They had an office for two guys, an opening and a salary for two guys. And they liked our script enough that they said, yeah, sure why not? Let’s hire those guys. And they did. And we eventually worked our way up to showrunner and so forth. And that’s happened to me a number of times in my career where I’d say, well,
Why don’t I just ask it? In fact, it happened just this year when in my food pursuits where I was like, I I felt like I wanted to do a collaboration with this place that makes fancy sausages. And I didn’t know we were going to do t-shirts or something. And I was like, no, why don’t you ask them, let’s do a sausage that’s Bill Oakley brand, Bill Oakley’s special hot dogs. And we did it. And they have been a big hit. Bill Oakley’s summer grill and dogs by Zeners of Portland. And in fact, there’s, we’re still selling them. We’re going to do a promotion.
at the stadium for them in a week or two. that was one thing where I was like, I felt like it was too much to ask them to make me my own special hot dogs, but they did and it was a big success. So that’s one of the things I have learned from that Simpsons experience is like, don’t be shy about asking for something crazy. I mean, you’re gonna get rejected 90 % of the time or 95 % of the time, but those 5 % of the times that pay off can pay off big.
Metwally — That One Time Podcast (04:41.038)
So how do you go about asking for something that’s kind of outlandish in a way that doesn’t come across as ridiculous or unappreciative? I think it’s all in the phrasing of the question. It’s just like you could just do something so as, don’t do stuff like, this is probably too crazy for you, but don’t say stuff like that. Just ask it out. hey, would you be interested in making a hot dog? Would you be interested in hiring us? Would you? That kind of thing.
You don’t have to ask in a humble fashion. But don’t be like a jerk about it either. You just ask like you’re a normal person. And I know that’s hard because especially with emails and texts, that kind of stuff really can go sideways fast with tone. People can’t tell what your tone is in texts and so forth like that. So you’ve got to be careful with the phrasing. But in general, it never hurts to ask. And sometimes it pays off big. So generally,
If you’re asking for something a bit outlandish in your mind, pick up the phone or meet them in person. It’s very helpful. Yeah. Or, you know, just be careful about your phrasing of email, a text or whatever. But yes, and people have a much harder time saying no to you in person. that also is something. But, know, that that’s a double edged sword. that you might get a no in person, a yes in person, and then they actually don’t follow up. Yeah, that’s Hollywood, man.
I had a hundred, it makes me mad. TV development is the most annoying thing in the world. And it’s the pitches when you pitch something and every time you pitch something and they all they claim they love it. You walk out thinking you sold it. And then three weeks later, your agent finds out, they’re going to pass. And that happens all the time. And then you find out they bought something much worse from some other idiot. And it’s a very frustrating business. And I’m actually kind of glad that it’s all going down the tubes. So how do you determine between
genuine interest and bullshit interest in that case. You can’t. The problem is every business is different. it’s certainly in many businesses are totally filled with phonies. And Hollywood is the one of the worst for that. the problem is that’s that’s saying. Famous saying about Hollywood. Hollywood is the only business where you can die of encouragement. And it’s 100 % true. And that’s
Metwally — That One Time Podcast (07:03.862)
I wouldn’t encourage any, but that’s the thing that I think is actually one of the best things about the event of the internet, which in general, I think is pretty bad. The ability of people to chart their own path in terms of stuff with like YouTube and podcasts and even TikTok without having to go through traditional channels. The traditional channels are calcified and they are, don’t even also now, as I said, they don’t even pay very well. It’s like you can spend years and years and years working on something for Netflix.
that they put on and nobody hears about it or sees it and it’s gone. And this has happened to multiple people that I know. And so I guess they did get the money for it, which is very, which is good. That’s very important. But if you want to work on stuff that people actually see, you might be better just putting it out there by yourself. Do you think there’s a trade, always a trade off between the money and the impact or can you do both? It depends on who’s giving you the money. That’s, that’s the problem. The person
who provides the money gets to call the shots. So when you sell your show to, let’s just say Netflix, they can make your life miserable and ruin your whole project and you have to do what they said because they gave you the money. So that’s, but now that’s the trade off. Now, if you wanted to do your show for YouTube, you could do whatever you wanted, but you’re not gonna get, you probably won’t get that much money for it and people may not see it. But now for, I’d say the trade off on Netflix is also people may not see it.
there, but you’ll get the money. anytime you say, anytime someone comes on board with money to any creative project, that’s going to cause trouble. It’s very rare to get a situation where the person or entity providing the money doesn’t want to tell you what to do. So it’s interesting you say that Netflix people still might not see it. I just had the assumption that the moment you’re on Netflix, you’ve just jumped to millions of views on a show. No. You’d be shocked.
at how many shows, doesn’t Netflix, it has like 30 new shows a day. And they’re like, they don’t, and you think they’re gonna get promotions, but only a tiny fraction of them get billboards or even get on the Netflix Twitter account, you know? And they can’t possibly, and so they use the algorithm to like, maybe this will recommend it to you if you’ve liked previous things, you know, in the past, but it’s, they’re such a, nobody needs this much content. Nobody needs this much content of TV shows.
Metwally — That One Time Podcast (09:25.878)
or anything like that. The only kind of content that actually there isn’t enough of right now is theatrical movies because theatrical movies have become so, have become unprofitable and you can’t get people to the movie theaters. But there are very few like independent kind of movies, independent movies that were like around in the nineties, you know, you don’t, there aren’t enough of those around and it’s because of the whole business model for that. But there’s way too, everything else there’s way too much of. can’t keep up with, you can’t keep up with anything.
You can’t keep up with your people. You follow on Instagram, let alone all the new shows that are coming out on TikTok, on Netflix, Hulu, Peacock, Paramount Plus, et cetera, et et cetera. Who needs that stuff? Speaking of history, how did majoring in history at Harvard help set you up for your career as a writer and now a food blogger? It didn’t. It just allowed me to spend all my time working on the Harvard Lampoon because I already knew the history to begin with. That’s the thing.
You don’t think you developed any interesting skills or lessons from learning history that you’ve applied? I mean, I have applied those things to some of the writing projects I’ve done. Not so much the Simpsons, but some of the things I’m doing now, like Space in 1969 and Space in 1972. But for the most part, always really enjoyed knowing about American history, especially 20th century history. So I took a lot of classes in 20th century history, most of which I already knew.
But I did learn a lot of interesting. I took an incredible class on the Vietnam War, which was really illuminating and so forth. But I didn’t really use any of that stuff. I mean, I can use it from time to time in things I’m writing. part of the, if I’d taken biochemistry, for instance, I would have been so busy working, I wouldn’t have been able to write all the comedy I wrote for the Harvard Lampoon. So the history, the that I knew most of the history enabled me to spend most of my time working on the lampoon and still graduate from Marvel.
So it was tactical. It was tactical to to enjoy an easier ride in Harvard than doing something STEM related. Yeah, for sure. You were in the office with other new guys when you first started like Conan O’Brien, who’s had now had a massive career. What was it like walking into that room at the time? It was extremely intimidating. This say, first of all, Josh and I had had we had a TV experience, but it all been kind of on a small time cable shows where there were four right, you know, us and two other guys. Right.
Metwally — That One Time Podcast (11:44.11)
and they were small potatoes. The Simpsons was our first job in like real serious TV, especially at a successful show. The Simpsons was incredibly successful back then. So when we got hired, they had only hired a couple of new people since the very beginning, Conan and us. so we would, like, as I’ve said in other interviews, it was like being hired at Saturday Night Live in 1978 for, you know, the Sid Caesar’s Hour in 1955 when like,
Woody Allen and Larry Gelbart and Neil Simon were all working there. These were the legendary comedy writers and they didn’t, was, people didn’t get in there, you know? It was rare. So we were very intimidated. We didn’t know what we were gonna be doing even. We didn’t know what the situation was. We didn’t know what story editors were. That was the title we had or what our job was going to be. And we didn’t know what it was gonna be like working there day to day. So it was incredibly intimidating and it took us weeks and weeks and weeks to get comfortable.
with the job there with, you know, pitching jokes and stuff. Well, that was that actually leads into my next question. Given that you were in the Simpsons in 92, you had an all star legendary cast of creatives in one room together. How did you end up finding the confidence to start pitching jokes and scenes among heavy hitters? We started really slow. Well, first of all, we barely said anything for the first couple of weeks. We listened. It’s probably a good, good general life lesson. Yeah.
It’s actually kind of annoying when new people come in and start pitching stuff that’s off target, you know? You could sit there for a couple weeks and absorb the general vibe. And what we started with was pitching very small things. You don’t say that we’re like, here’s a funny, like we need a funny sign for this place. We need a funny turn of phrase for Kent Brockman to use. And I remember writing down the things that we got in the script and at the beginning they were all kind of like just funny turns of phrase or like a funny sign or whatever. And gradually over time,
our track record was enough that we started pitching the bigger stuff. And then when we turned in our next script, which was very well received, we realized, and then also everybody else left. they all, most of the old writers left too. we became, Conan and us became the most senior writers on the show after having only been there for like eight months. Okay. So, so listen, add little bits of value and then wait until the opportunity arrives to actually really push.
Metwally — That One Time Podcast (14:09.398)
I would say that for sure. And also, the other thing that is not common sense to many people is don’t criticize other people’s ideas. This is one of the things that is most hated in writer’s rooms and people don’t realize it, is when you shoot down other people’s ideas, especially without providing an alternative. The thing about it is, if you have, there’s a very diplomatic way to say, that’s great, but what about blank? You could do something like that, right? But you’re just like, that’s not gonna work.
We did that before that kind of thing. That’s how you become hated really fast in the writers room. Yes. I was a better technique because that’s a really important thing to understand. The better technique is either to keep your mouth shut and wait for the show runner to the show runner will feed. We’ll say that’s good or that’s bad or we’re putting that in. We’re not putting that in. secondary to that is you pitch something like that. You pitch something else. You don’t say you don’t you don’t have to respond to everything that comes out of everyone’s mouth.
What you need to do is just pitch your own idea. So like if you don’t like that guy’s idea, you pitch your own idea. But you don’t say, mm, that’s not gonna work, or mm, I don’t think that’s very funny. Don’t ever say stuff like that. Just pitch your own idea and in the flow, if people like your idea, it will go in, or people will laugh and the showrunner will put it in. There’s no need for, the only person who needs to make a judgment about the quality of the ideas is the person running the room.
Sometimes that person takes into account other people’s opinions. Sometimes they don’t. So as a showrunner then, what is an effective way to shoot down ideas without becoming being becoming hated as well? You don’t say anything. You just don’t put it in. You move on. just like action to say it all. Yeah. You say it. People when people see you putting the line and you like, people see you laughing or you’re putting the line in the script.
Then they know it worked. Everybody, a lot of times you can tell because everybody will laugh or many people will laugh and like that’s a very good line or whatever. The problem is that in writers rooms people don’t pick... The only thing that really matters in a writers room, TV or comedy writers room, is they can laugh. People won’t pitch the straight lines, they won’t pitch the emotional lines, which is a big problem with rooms that rooms sap, often sap the emotion out of script or the character development out of a script because they don’t, they only want to pitch jokes.
Metwally — That One Time Podcast (16:30.144)
So you need to have a show runner who can either keep that stuff in or a first draft that has the stuff already in it. Like that’s the kind of thing you would get from John Vede at the Simpsons is a heartfelt episode with a really good story and a lot of emotion that didn’t need to be tinkered with in the room. Eventually you ran the show in what was considered some of its best years. It’s a lot of pressure. How did you handle the pressure? What techniques did you use? Well, part of what made it better was that I was
doing the job with Josh, who was my best friend. So we were able to split the work between the two of us. If it had been a job for one person, which it had been under David Merkin, that’s a lot of work. And so we split the work, and each of us would be responsible for alternate episodes and whatnot. And that made it tolerable. Also, we tried to have a good time. We really liked working at the Simpsons, and we really liked being able to be in charge of it, because nobody was giving us any notes.
Nobody is telling us what to do. And we knew it was the best TV comedy of all time, or at least that had been our opinion when we were hired there. So we were enjoying doing it, enjoying it, writing it for ourselves. This is also before the internet really existed. So with a few exceptions, we had no idea what people thought of the episodes. We just did ones that we thought were entertaining. Yeah, that makes sense. And how did you keep the creative innovation flowing?
We tried to keep things light. tried to, well, we also tried to keep people morale. I say this, you know, this is something that work. People, I think is the lesson that all listeners could take into account. Maybe something helpful. People don’t pay attention to morale anymore, you know? Morale, used to be big deal. Like in the army, they were officers who were in charge of morale. You know, people, you gotta give your spirits up. like, sometime I think in like the 80s or the 90s, the whole idea of morale.
of people, the morale of your employees was cut out. It’s just like, we don’t have time to worry about that anymore. And like, having people who, having your employees be cheerful and happy is important. And it’s important to, it’s important to keep people in good moods. If somebody’s in really bad mood, we would take them out of the room. We would say, you should go right. We would take them and have them work on something else or we’d split into two rooms and one room.
Metwally — That One Time Podcast (18:56.486)
One of us would bite the bullet and take that person, the The naughty corner. And work with that person or work in a smaller room with them because that person is going to tank the vibe of the main room. Or they’d go home or we’d send them home sometimes. like, so we wanted to keep things light. We wanted people to have fun. We didn’t want to stay too late. We stayed late a fair amount, but we never worked on weekends, unlike almost every other show.
And we let people have their, we wanted people to shine. We wanted people to like turn in great first drafts so that we didn’t have to rewrite them. So we wanted people to take, to do their best work and be in a good mood and be proud of it. And like I said, more morale, we tried to do things like.
surprising things like we all went, we all took off early to go see Independence Day the day it premiered and things like that and stuff like that. You know, any job, there’s going to have things where it’s not that fun. But I’d say the weird thing is that most employers these days, with the exception of places that totally fuck you over, like Facebook, you know, has a huge Facebook, for example, whatever they have, they have all sorts of, they have a pool table, they have video games, they have cafeteria, they have all these chefs on premises. Yeah, but they totally, they ruin your life.
So like that’s like that, yes, they do think about morale, but it’s not for the reasons you would hope. It’s for its insidious purposes. It’s not for like, we want our employees to be happy because they do good work. No, it’s at Facebook. It’s like, we want our employees to never leave this building. Yeah, I’ve noticed that in some jobs where they’ll provide you lunch, but they don’t give it to you at your desk. So you just keep working and you don’t leave. Yeah, things like that. Yeah. I tried to I called that out at a job and I didn’t last very long in that job.
I think it’s particularly in today’s environment. think that a place that really seemed to care about the employees morale would stand out as being a great place to work. I wonder why it’s changed. Maybe it doesn’t really matter anymore for the outcomes. I don’t know. The culture shifted. I have no idea. I think so. I think it’s become all about the numbers in the bottom line and so forth. And I also honestly think that there probably was
Metwally — That One Time Podcast (21:10.338)
there may have been some holdover between people who had been in the army where they really were worried about your morale, you know? And now we never have any, most people who’ve been in the army aren’t in these positions anymore. Like they, I think there’s probably that. I also think that part of the thing is that everyone, there’s so much like HR, there’s HR type things about like, we can’t have that, we can’t serve alcohol because someone might get intoxicated and say something, whatever, you know, fuck that stuff. I’d say, I’d say, on.
I guess I have an opinion that is considered... I don’t mind serving alcohol at the workplace. I know that’s not permitted, but I’d say that was probably... that probably helped lubricate... I don’t know, it probably helped lubricate social dynamics in the workplace. When people drink together, there’s always someone who’s gonna have a bad time, there’s always someone’s gonna say a remark that was not intended, and then things are gonna go south. And there’s like... but you know, if you have a sterile workplace that’s no fun...
That’s also bad. So basically what I’m hearing is you guys are getting blind drunk in the writers’ We didn’t drink in the writers’ room, but we sometimes did drink during dinner. And I know at Mission Hill, yeah, at Mission Hill for sure. mean, people drink to varying degrees. But we definitely had parties at Mission Hill. We had the best Christmas, worst Christmas party I ever had, and it was totally soaked with alcohol, and everybody had a great time.
And that would have been so illegal, so not permitted today. I mean, maybe it’s the secret to good creativity is getting loose. It certainly helps. Someone said, someone famous, author said, write drunk, edit sober, or whatever. And I don’t remember whose quote that was, but it was a fairly famous author, editor. Ernest Hemingway. Yeah, I thought it was him.
Yeah. Well, speaking of things you’ve written having a big impact, Steamed Hams is one of the main things you’re known for and how it became a huge meme decades after you wrote it. So can you walk us through how that scene got developed and whether you felt like you were onto something or it was just you threw it out there and that was it? That was what it was. So that scene, as I think I said,
Metwally — That One Time Podcast (23:34.284)
Superintendent Chalmers was my favorite character, and one of my favorite things was when Superintendent Chalmers, Skinner would lie to him, and Chalmers would question it. But previous, and it had happened many times prior to that, and Chalmers would always question him once and then drop it. And I thought that was very funny, but I thought, what if one time he didn’t drop it, and he just kept nailing Skinner to the wall about these lies, and the lies became more preposterous? That was the whole genesis of Steamed Hams.
which was an episode, that was in 22 short films about Springfield, which was an episode where every writer got to pick their favorite character and write a scene for them. So I wrote that thing for them. Now, none of this stuff was popular when it first came out. This episode, the table reading wasn’t that great. No, we never heard about the episode. It was broadcast and it went into oblivion, like everything back then. But this one, we did hear things about certain episodes, like Frank Grimes or whatever, but this one, we never heard anything about. And the thing about this episode is that I have to say,
Like what I think a lot of our episodes were episodes for Simpsons fans because we were writing these things back then, Simpsons fans were children for the most part. Like there weren’t that many Simpsons fans. This show has developed this incredible following because it was in syndication for so many years. And so people grew up watching it. That was not the case in 1996. Like in Australia at 6pm every day. Yeah. And so that’s how people know these things. And 22 Short Films was an episode for Simpsons fans.
because it wasn’t about the family, it was little vignettes of minor characters. And so at the time, it went into oblivion. Now 20 years later, it became very popular because people had grown up and the Simpsons fans were much more intense than they had been. So that episode took on this weird life of its own, starting in 2014. And it started in Australia with, as you may know, people calling Woolworths, which I guess is one of their big grocery store chains,
and asking for steamed hams. And then, Woolworths got in on the game and they made a funny video where they put up signs in the store that said, we don’t carry steamed hams, but you’ll enjoy our ground beef, whatever. And so then it somehow crossed the ocean and started taking off in America. And between 2014 and 2018, it took off in this incredible way that I could never have foreseen. And it became the internet meme of the year in 2018, according to one source. And people remixed it tens of thousands of times.
Metwally — That One Time Podcast (25:56.148)
On YouTube. In fact, it’s still being remixed to this day by some very talented people who are making these things that look like it’s a German expressionist film. It’s an Ottoman Empire shadow play, whatever, and things like that that that are bafflingly complex and so good. And so anyway, yes, what happened was around that time was when I started to get into the culinary proceed the proceedings and I decided that I wanted to link. I was the author of steam Tams. I want to link my culinary things to steam Tams so that I could.
maximize the potential for being recognized. And you’ll see right behind me, that’s my neon sign for the Steamed Ham Society, which is my culinary club on Discord. But I actually do a number of other things that all have steamed hams. I give out the Steamy Awards every year on my Instagram, which are for foods that I try. I have the trademark for Steamed Ham’s brand hamburgers, which I’m going to be releasing in some form in the next year or two. it’s taken, and particularly given that I love hamburgers.
It’s very appropriate that steamed ham is a euphemism for hamburger. that’s it’s been something that it’s been a it’s been a blessing to my as I transition into my culinary career to have this as one of my calling cards. Yeah, it’s great. And it’s a perfect segue, isn’t it? Before we move into that segue, I’m curious, how did you ultimately decide who should shoot Mr. Burns? We did not, believe it or not. Josh and I.
The episode was Matt’s idea. Matt Greening came into our office, and he’s like, yeah, we should do some sort of stunt like who shot Mr. Burns? He’s like, he shot JR, obviously, based on who shot JR from Dallas. And we’re like, hey, that’s a good idea. So we made up a whole story that involved it. And it was a mystery. And Josh and I wanted it to be Barney. We wanted it to be Barney who shot Mr. Burns and then went to jail for several seasons and then came back a different man because people were already getting tired of Barney’s drunk guy routine back then.
Then we took it to the story conference and James L. Brooks, wisely, because he’s Brooks and he’s all about the family and the emotion and that’s how he becomes so rich and famous, he was like, it should be a member of the Simpson family. And we couldn’t figure out any way that that would logically work, except he said, what if it was the baby? And he’s like, that’s the least, you’d expect the baby to be the least likely to shoot Mr. Burns. And we were like, we left the story conference saying that’s.
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We don’t like that idea. We don’t like that idea because it’s going to be an accident. We don’t think Mr. Burns should be shot by accident by a baby. And then David Merkin, who was running the show at the time, said, well, what if it wasn’t an accident? What if we somehow indicated that Maggie had done it on purpose? And then we were like, that’s pretty good. And that’s how we wrote it. Yeah, it’s a great segue into, sorry, it’s a great development of a scene. I absolutely love it.
With you guys got a lot of awards. You had three Emmys from the Simpsons, is that correct? But I want to understand what were the failures or tough moments during those years that taught you more than any award might have? Well, I learned a lot about what does and doesn’t win Emmy awards for one. We learned about we submitted the wrong episode in season seven for our Emmy consideration and lost Pinky in the Brain. I would have redone that.
for sure because they were like the emotional ones. And at the emotional ones, we should have submitted Mother Simpson that year rather than the 3D Halloween thing, but the Vimy Vodors were not impressed by the 3D as we thought they would be. They liked the emotion, the heartfelt, whatever. So that was when we submitted Homer’s Phobia the next year and we won. So I learned that. What other hardships did we learn? I think the thing about it is we learned people skills.
We learned a lot about the people skills of managing 12 very difficult creative guys, mostly guys, almost all guys who are difficult, opinionated, and so forth. And we learned the sort of diplomatic skills that I already touched on earlier today about dealing with morale, keeping people’s spirits up, letting people participate in the process, and so forth, and making people feel like they’re enjoying their job and they’re getting something out of it.
was part of what we learned. we’re like, you know, I think various writers probably have different opinions of our success in those matters. But I think we learned a lot about managing people, which is a skill that most a lot of people don’t seem to give a shit about. Yeah. Yeah. I mean, there’s a really good book about this. I’m sure you learned all the skills, similar skills from Ed Catmull, Creativity, Inc. about Pixar.
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and just how to manage high level world class creatives. It’s a whole thing in itself, it seems unbelievable book. Yeah, really, really good book. You should read it. Yeah. So it’s called Creativity, Inc. Overcoming the Underseen Forces that Stand in the Way of True Inspiration by Ed Catmull. That’s great. So wrapping up on the Simpson side of things before we dig into some of the food stuff, I’d love to...
Get your thoughts on the Simpsons ability to predict the future. What’s going on here? You’ve got Disney buying Fox, Trump becoming president, Lady Lunch-Dro is putting horse meat in the food, the Higgs boson particle mass actually being somewhat close, three-eyed fish. I can just keep going. What is going on here? Okay. I’ve done a number of interviews about this topic, so I have it boiled down into a few different categories. The most common category is something that the Simpsons, that didn’t even appear on the Simpsons, that’s made up.
that someone uses AI to generate. And then every British newspaper is like, did the Simpsons really predict the Baltimore Bridge collapse? No, somebody used AI to make that frame that looks like Homer’s in Baltimore watching the bridge collapse, which would never have appeared on the show. But you get to write an article saying, the Simpsons really predict? So 80 % of what you see is just clickbait from mainly from these British tabloid sites that are generating this stuff all day long. So every time there’s an event, someone makes a Simpsons meme of it.
to get this going. a bad way to get some clicks. It works. It works. OK, so that’s one. OK, then. The ones I said were all in Those are in the show, yes. OK, so now we go to the three actual categories of things that were in the show. the tier three is stuff that is so old that people didn’t hear about. We’re making stuff, a fun of stuff from the 60s and 70s that people had never heard of. So it’s the first time they heard, like for instance,
When we did this episode, Josh and I wrote this one where the Osaka flu comes to Springfield. And during the pandemic, everybody was like, the Simpsons predicted the pandemic. And we were like, no, that’s a reference to the Hong Kong flu of 1970 that we heard about as kids. And so people who grew up watching The Simpsons, the episodes are so old, we’re referencing stuff that they never heard about. And it’s the first time they heard it. So they think we predicted it. Okay, that’s tier three. Tier two, and this is a very common one, is what’s the stupidest possible thing that could happen?
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Part of writing comedy is the people of Springfield are dumb. They’re dumb and there are yahoos and they always get riled up into a mob over stupid shit. Well that happens all the time now. That happens in real life. So the jokes we were making are about like what’s the stupidest possible thing that could happen? The stupidest thing happens very frequently these days. So it’s not as much of a satire as it once was. That’s the category too.
This is an example of fate loving irony. Yeah, for sure. And then there is category one, which is things that we actually did predict. And it’s because those things that you said, like Trump, for example, were well, that’s an example, as Dan Graney, who wrote it said, that was a logical last step before hitting rock bottom. And so that’s part of the that that’s part of it. Some of the things are just seems like there’s an inevitable flow of history like Fox, like Disney buying Fox.
And it just because also because when you have 40 years worth of episodes, you’re going to get a few things right. So but in answer to your question, it’s because there’s a lot of smart people thinking about the way society is progressing. And sometimes they’re going to be right. A lot of times they were just trying to make a joke about the way stupid things happen. And that turned out to be true. you? Well, when you were writing, was your primary aim to be funny or actually provide some deeper insights into the cultural state of the world? Well, it was a combination of the two, depending on the episode.
Sometimes it was to be funny and you know, for instance, like in the prohibition episode, that’s just entirely funny. There’s nothing about the state of the world in that. It’s just all jokes about prohibition. Then there’s other ones that are like that, that have a little bit more to say about society, like the immigration one with a poo and whatnot. And so it really depends on the episode. Just quickly though, I love doing this podcast. If it’s positively impacted you in some way and you would like to support us, please subscribe.
By subscribing, it allows us to build a much bigger base of listeners, which results in better guests, better production, and a better show overall. Alternatively, please take a look at the affiliate links of the products that I use and love in the comments below and consider purchasing using those links. They’ll give you a discount and they’ll also provide the podcast a small kickback. These are two very easy ways for you to support us.
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as we continue to grow the podcast that we absolutely love doing. Thank you for your support. And now back to the episode. So you leave the show at its peak and switch gears into food vlogging. And you now call yourself a professional food enthusiast. How did you go from writing TV shows to reviewing fast food restaurants? It should be said, I barely do fast food at all anymore. I’ve sort of transitioned into more of like just general American food. Yeah. But I, it started as a hobby.
I started doing it on Instagram as doing just basically doing short one minute fast food reviews back when people weren’t really putting videos on Instagram when they were just putting photos still. And it started to get a lot of press. People enjoyed the information I was providing. And then over the course of the past six years, honestly, I sort of branched out into all sorts of other fast food has become not as interesting as it once was. It was very interesting during the Popeyes era when Popeyes was launching that chicken sandwich and everybody was going berserk.
And there was a lot of competition, new things coming out. It’s sort of stagnated. And I’ve also just become more interested in other things like these, you know, unusual American foods. And that’s what I actually do these days, or at least this year, is I host these ticketed dinner events where we have, serve a menu of unusual regional American foods like Rhode Island clam chowder, Cincinnati sauerkraut balls, St. Louis gooey butter cake, Cincinnati chili.
We serve these unusual dishes that you’re not going to find anywhere in your town. And I do a funny talk about it with a lot of Funny Simpsons references in there too for fans. So I do that and I do other food things as well, just because I find it more interesting. I also do, by the way, I still do comedy writing, I completely, it’s 100 % devoted to my own thing, which is this audible thing I’ve been doing for six years, which is Space 1969 and Space 1972, which is the sequel coming out next year.
Yeah, cool. with the food that builds America, what patterns do you see that today’s food, fast food businesses and food startups are actually missing? Because you said it’s gotten a bit lackluster. They’re in business to make money, not to entertain me with interesting new foods, right? And so for instance, Burger King has Burger King, which I used to really enjoy, has done a really shitty job with new foods and having the foods be any good. And that’s an example of an American
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Part of the problem is that in America, these fast food chains are generally too big to innovate at the level they are. you see, when people like me read this stuff, it’s like McDonald’s in England has all these new cool burgers. McDonald’s in Canada, McDonald’s in Pizza Hut in China. It’s all these incredible things. We never get any of this stuff here. The only place that is innovating at that level is Taco Bell. But Taco Bell just combines the same nine ingredients into a different thing every, but they do it every six weeks.
So they are doing that kind of thing. basically operating on kind of a Japanese level of innovation, whereas everything else here in America is stagnated into kind of a 1950s kind of, here’s the menu. Shake Shack, God bless them, does it occasionally. They come out with new, like the Korean barbecue burger or whatever, but they’re kind of hard to get to when they’re much more expensive. What do you mean by Japanese level of innovation? I mean like Japanese, Japanese.
McDonald’s, Pizza Hut, Domino’s, or 7-Eleven has a large number of very interesting diverse menu items that change frequently. Tell me about your next endeavor, Steamed Hams. Well, as I said, you would think that Steamed Hams, because I wrote it for Fox, which is now owned by Disney, would be property of Disney. However, they either didn’t notice they were there asleep at the switch or didn’t care.
when I trademarked the phrase steamed hams as a food item. So as I said, it’s a euphemism for hamburgers. So under some auspices, it might just start out here locally in Portland with a local place. They’re gonna be selling officially licensed Bill Oakley steamed hams. Now, I also would like to get in business with a really quality meat producer like Pat LaFrieda in New York or whatever, and maybe make frozen steamed hams as well. So that would be something that would also be fun, but I’m just barely beginning to scratch that surface.
that sounds exciting. Has someone from Lego hit you up yet from Disney? They can’t. I have the trademark. I mean, I guess they could try and they probably would win because they’re bullies. I have no. at the moment, I have the trademark and most likely. Well, it depends on how much money they have. How much would you want? Several million dollars, I’m sure enough to retire. And then I would then I would stop worrying about that. But.
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My guess is they don’t care. thing is, Disney lawyers have better stuff to worry about like Cinderella and Mickey Mouse and Iron Man and Thor than a phrase that appeared on one episode of The Simpsons they probably never watched and never heard of. know, the lawyers are busy. They’re not Simpsons fans. Yeah, fair enough. So what makes a fast food item shortlist for the Steamy Awards? It has. And we probably should explain what the Steamy Awards are for some context. On my Instagram, which is
devoted to all sorts of food pursuits, but also some fast food. At the end of the year, I give steamy awards, generally there’s 10 awards in 10 different categories, and often they’re given out by a celebrity of some sort, or a friend of mine, or something like that. And it’s a very short award ceremony, and each category is like best overseas condiment, best new potato chip, best frozen food, and then there’s usually two to three to four fast food categories. one of them is the most, one of them,
A couple of them are bad, fast food disappointment of the year. There quite a few of those. But then what happens with a fast food, the big award usually is generally new fast food item of the year. it’s got to be something that is, it’s not just going to be a sauce from McDonald’s, although it could be if it’s an amazing sauce. It’s generally a new item from one of the fast food places that is somehow delicious, that I couldn’t stop eating. What people don’t realize,
is that I don’t finish food if I’m not loving it. So when I do a video, people are always asking, how come you don’t weigh 500 pounds? Well, weigh, I’m not weighing 500 pounds, but I don’t eat like this all the time and I don’t finish the food in my videos unless I’m loving it. So generally what happens, and it happens a couple times a year, I’m like, oh my God, this is delicious and I finish the item. That’s the thing that goes on the short list for the Steamy Awards.
So what usually makes you want to finish something? It’s a combination of textures and flavors. I like things that are not. I prefer a burger, as you can see in that sign. I prefer a burger. Some people are like, I don’t like salad on my burgers. And I’m like, you got to be kidding me. That’s what makes a burger. Burgers can be great without the stuff. But for me, it’s lettuce, tomato, onion, mayo, pickles on the burger. That’s what makes it a. So.
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So that’s, you know, I’m often looking for a combination of flavors, textures, cold lettuce, like the McDLT, the best burger in the history of McDonald’s was the McDLT because it had the cold side cold, the lettuce and tomato, and the cheese was cold too, which people always complained about, but I thought was great. So I like a combination of flavors and textures, and I like some little spice sometimes in there too, but that’s generally what it is. And it’s something that doesn’t taste like everything else.
Yeah, yeah, that makes sense. And what do you think is on the shortlist now? Something that I could try in New York that is potential for the STEAME Awards in 2026? That is a good question. I haven’t had any fast food items this year that I have truly loved, I don’t think. And I’m not even sure that that category is going to be in there this year. I think it’s been a very slow year for fast food, which is why I have not.
Honestly, the best things are the same things that Taco Bell is dragging out of the closet. now they have, Taco Bell has this 90s menu, or this 2000s menu, Y2K menu, which is all the items that people loved in 2020 to 2010, 2020 to 2019, including the Double Decker Taco, which are my favorite Taco Bell item. That’s probably gonna end up doing it. Like, that’s the best item of the year, is the item that they had canceled and dragged back out for this promotion. It says something about the state of creativity right now.
Yeah, mean, like I said, Shake Shack does it. And I love the shake shack comes out with some new thing like the Carolina Gold Burger or the Korean barbecue burger. But Shake Shack is a nuisance for me to get to and it’s really expensive. So I don’t go there as frequently as I would to McDonald’s, which is just a few blocks away. Yeah, fair enough. Look, wrapping up, I’ve got a few general philosophical questions about the philosophy of life. And I wanted to get a
understanding of what the most beautiful thing you’ve created is. I don’t know that I would say. I think it would be hard to say anything. You know, it’d be very cliche to say it was my children. So I’m going to say that. they but I don’t know that any of the things I have qualified would fall into the realm of beautiful. I think they fall in. I think a number of the things fall into something like very satisfying. Like, and honestly, the thing that I most
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The thing that I’m most proud of writing and producing is Space 1969 and its sequel because it’s something I feel like only I’m the only person on earth who could write and produce this and I’m grateful to Audible for letting me do it and I can die happy knowing that I did those, that I did those, I did them exactly the way I wanted, they let me do it, they spent a fortune producing it and it’s so, it’s so, many of the jokes are so obscure but people loved it, it became a best seller. So that’s why I, it’s
That’s the most creatively satisfying thing I’ve ever done. I wish it paid a lot more money, but it’s okay. It’s okay. Was there ever a moment where your life changed in a flash? Yeah, when we got hired on The Simpsons. We went from unemployed guys who were going to be... We went from guys who were unemployed and were desperately thinking of trying to work at the State Department or whatever to being hired to work full-time on the best show in TV history. At its peak, I would consider it.
That was, I remember that vividly. remember the day and I was like, this is amazing. I can’t believe this happened. And what’s the biggest thing over the last two years that you’ve changed your mind on? Broccoli.
I don’t hate it so much anymore. I figured out how to, I hate cauliflower still, but I don’t hate broccoli. What’s wrong with cauliflower? I don’t like the flavor of it. I don’t like the weird bitterness of it. Broccoli, have come around, I don’t love it, but I found that you can make it on a sheet pan, olive oil on it, and put some stuff on it. You can make it in the air fryer and sprinkle some stuff on it. Especially you want to put some sriracha or honey or something like that, it’s good. I don’t, oh, eggplant too.
I’ve had, I hated eggplant for all my life until I started making it, like roasting it and cutting up into little squares and I made kind of a healthful, what was it? Some sort of Middle Eastern type dish that I’ve been eating for lunch and stuff. So those things are two things I have, like, cauliflowers alone hold out, but in most of these vegetables that I hated for my whole life, I have come around on now. Yeah, I love doing really thin eggplant pieces in the oven.
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blasted, like kind of crunchy with some, amazing. Well, wrapping up, is there anything you’re excited about that you want to let listeners in on? Well, there’s a long laundry list of things, many of which I’ve touched on here. First of all, I’d like people to follow me on Instagram, on that Bill Oakley. I would like people to come to my dinners, which I’m having, I have, I’ve had 14 of them all over the country this summer, and I hope to have more. I’m booking more now for the fall and I have a special holiday edition of the dinner.
that I’m doing in December at a few places. And these are fun events. if you work in a restaurant or you’re a chef that would like to collaborate, just send me a message on Instagram. And I think we could have a blast doing it. So that’s one thing. Also, be on the lookout for Space 1972 coming out next summer on Audible. And in the meantime, you can listen to Space 1969 on Audible for free if you’re a member. And if not, you’ve got to pay $29.99 or whatever to get it. But it’s a
my favorite thing I’ve ever written and it is, I think you’ll find it entertaining. I’ve heard that it’s become big among high school students and stuff, which is not something I expected because it was, it’s all about the 60s. but I guess it’s got enough, it’s kind of Futurama style comedy. People have called it past-arama to some extent. So it’s kind of like that. I guess the younger audiences are looking for the nostalgia of the world. I hope so. It certainly is the kind of thing I’m interested in writing. it’s like, by the way,
It’s not like a fond trip down memory lane for me. I was only three years old in the 60s. I guess it is because I’m interested in history and the whole era of that era. It’s not like I’m trying to, I’m a guy reliving his youth. This is stuff that I didn’t live through either, but it’s fun to write about. Yeah. And my last question for you is why do think we’re here on earth? I think there’s some sort of metaphysical thing that I haven’t figured out that is probably some, probably
related to some, I think Buddhism, can’t, I who might speak to this, but I’ll tell you, I believe that of all the things I’ve heard, that the Buddhist thing seems, sounds like it’s the most correct, and that we’re here to learn something, we’re here to learn some set of something, skills or something that we don’t understand yet, for stage, for the next stage of existence, which who knows what that is, but I believe, I think that’s of all the things I’ve ever heard about the afterlife and.
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and existence and quantum, the way that it blends with quantum physics. That’s the one that makes the most sense to me. Okay. Well, thank you, Bill Oakley. I appreciate your time. Thank you for coming on. Nobody’s ever asked that on any podcast that I’ve ever been on. So good work. So good. here to, um, I just like to wrap it up with just a general idea of what the world, why we’re, why we’re doing this. Cause you get the most interesting answers from a lot of people. A lot of the time people just say to love.
Probably 60 % of the time, which is really, really sweet. Yeah, well maybe that’s part of it. Maybe that’s what you’re here to learn about. I don’t think you’re going to know for sure for quite some time. Yeah. And if you’ve enjoyed this episode, please go to YouTube. Search that one time without a MetWallet. Click Subscribe, like the video, and leave us a comment.
