How Hollywood Won This Emmy-Winner Over
From Chico to Santa Barbara, to NYC to Hollywood: why the award-winning writer and author Jason Ross has changed his mind about LA
Full disclosure, I have known today’s guest since he was a teenager. Jason Ross and I went to college together at UC Santa Barbara and met at the infamous student newspaper, The Daily Nexus, where he eventually became Editor-in-Chief.
Jason saw me accept a state journalism trophy while I was wearing a dress. And I have watched him accept several Emmys in a sharp tuxedo.
It has been a joy seeing Jason take what he had in college, a delightful interest in news and satire, and turn it into a wildly successful career. It’s also nice to hear him say how much he loves Hollywood, the place.
But first, the dream.
Tony Pierce: In many ways you have fulfilled the Hollywood dream. In fact, you did something that only a handful of people have done, which was you wrote for a New York show while living in Hollywood.
Jason Ross: We call that The Reverse John Bines cause he, he was writing for Jimmy Kimmel while in Brooklyn.
John was famous in our circles because he was living in Brooklyn where he wanted to live and yet writing for Jimmy Kimmel here in Hollywood.
Um, so yeah for about a year-and-a-half 2013-14, I was writing for [“The Tonight Show starring”] Jimmy Fallon from Los Feliz which was great in a lot of ways. It was also very limiting because I didn’t get to know anybody at the show. There was never going to be any advancement for me at that show.
2013? Did you even have video chat going on?
It was mostly email and it worked very well. I later learned that the reason it worked fairly well for me is that it was running exactly the same way for the people in the office.
They were getting the same emails I was getting and that’s how they were working too. And they were submitting by email the same as I was submitting by email. And so a lot of them were sitting in the same room, but they were working individually and getting the same type of assignment emails that I was getting.
The thing I was missing every day was a meeting with Jimmy Fallon where he would be reading the jokes for the first time.
And there was an interesting setup there where the writers were the audience for their own jokes being read for the first time, by the host, as he picks which ones he’s going to go with and which ones he’s going to kill.
And so that was, for me, a very awkward meeting. So I was, “I don’t particularly need to be at that meeting. I don’t mind missing it.”
My perception of a writing room in let’s say The Daily Show or these others — and please correct me because I’m sure I’m wrong — it’s a bunch of guys, Doritos, weed, not a lot of writing, not a lot of jokes, just a lot of nonsense. And then finally, “okay, let’s get the jokes together.”
In the 1970s there might’ve been rooms like that. The Daily Show is a very business-like, but also a very joyful place.
We had a lot of fun in that room and the job — I saw the job, and I think most people did, as making everybody else laugh based on whatever idea we’re kicking around, and trying to pitch out the funniest idea.
But also what a lot of people don’t understand is that a room at a late night show — those aren’t room-written shows. So the room is something where, at least at that show, it was about a 90-minute morning meeting.
That was the room most of the time. And that’s when we kicked pitches around, when you would pitch your own ideas when you would build somebody else’s pitch and try and figure out what you’re going to do that day or maybe the next day.
And then later in the day, when things are really getting written, and we’re getting notes back, we would have what we call Gangs, or at other shows, Gang Writes.
A gang was when:
- there’s this one joke that we need replaced
- there’s a punchline we need
- there’s a new idea that we want to put in right here and we need a joke on it.
And so now everybody who is available gets in one room and gangs-out — six or 10 punchlines on this one idea.
And that’s a very focused 15 or 30 minutes right there.
That sounds really fun.
It’s great. It’s great fun but there’s no weed. There’s not much in the way of snack foods away from actual mealtime.
Meal time’s a big deal. I don’t want to say we didn’t eat. We ate pretty well at The Daily Show because they had to feed the crew every day, based on their union contract and it was not that much more money to just feed everybody And it kept everybody in the office… so we ate catered lunch four days a week. It was really great.
About the second half of the run that I was there, we started doing a daily 3:00 PM meeting, which was for the following day. That was a slow time when production was busy producing what we had written up until then.
Another thing that people probably would never know about The Daily Show, because writers get so much of the glory at a show like that, but there’s a room of what they call studio producers… on most other shows they would be called segment producers.
They are as good as anybody in the business. I mean, just ferocious, same-day producers who can take something — and I bring them up because a lot of the pitches, a lot of, “hey what is topical today?” would be brought in by producers. Part of their job is to follow what’s been on the news.
We were never short of material at The Daily Show. That was never an issue. It was always a matter of, “is this something that we can have an original take on?”
George W. Bush, and I’m sure Trump, for the writers who had to deal with Trump… I feel like it was hard because of what you just said. What’s the take that not everybody on Twitter, nowadays, has, ‘cause Twitter is pretty funny and anybody can be funny on Twitter?
The professionals are generally a little bit better at it. But still Dave Itzkoff tweets something funny, kicks your ass, and now you’ve got to forget that for a second and have your own take on something. That’s got to be hard.
You’re absolutely right. That Twitter has yanked the rug out from under late night. It just has happened.
Late night can still do it better, it can do it with production values, it can do it with video and sound and little parody ideas that they can put together. But, the novelty of that joke… watching Carson back in the ‘80s when we were teenagers, it was almost like church in the way that it was like a special hour.
This is an hour where we’re gonna laugh about the news during this monologue. This isn’t something that we’re going to take seriously. This is something we’re gonna laugh about for these 15 minutes of the day. And now it’s all day long, all the time.
Which is why I give props to guys like Bill Maher and John Oliver. It takes them a week to get their show up.
Let’s say Matt Gaetz does something dumb on Monday. You would think all the jokes have expired before Friday. And yet Maher’s monologue is still awesome. Every single week. And the same with John Oliver. They do figure out how to have a different joke and a different take. And you’re like, “why didn’t I think of that?” which I guess is the highest compliment.
That is a compliment to the staffs of those shows. And maybe in that way, you can say that Twitter is just forcing everybody to be a little bit better. I still see it as a ceding of ground that now everybody in the world is making jokes about stuff where it used to only be a couple hundred people doing it.
Writing in Hollywood compared to New York
Let me ask you about what it was like for you to write in New York. My perception would be in New York would be almost impossible to write in because there’s so many distractions. We’re two different people, but if I can get great Italian food at 3am, suddenly I’m not in front of my computer anymore. I’m walking down the street, getting Italian food. Whereas here, I guess I can walk to a taco truck, but I’m probably not gonna, cause it’s not the same
There are hours of the day when you get things done because you feel like the town is shut down around you?
Yes. That’s why I go to sleep at 6am.
That’s interesting. I guess I’m distracted by other things. I’m not distracted by Italian food in the middle of the night. I’m distracted by the Internet. I’m distracted by the easy stuff that you’ll get anywhere.
For the most part, I don’t buy anyone’s argument that one town is hard to write in and another town is easier to write in. It’s always a matter of your discipline or if you’re lucky enough to be in a cloistered kind of situation, like a TV show, where you have to show up at 9:00 AM and write something by 11:00 AM . You’re going to do it.
That’s the thing, hard deadlines are a blessing because if I’m sitting in this little cubby and I’ve got no deadline, I’m probably not going to finish. And so The Daily Show was probably easy, as far as that goes.
I had a friend when I first moved to New York, he was a friend from Chico. His name’s Alan, and he was a cellist — a professional cellist who went to, I think, Morningside conservatory.
He talked about Johann Sebastian Bach and how he lived as the composer at a the church somewhere. And his job was every single week to write a Cantata or something for that week’s mass — an original piece of music, every single Sunday.
Deadline.
God’s deadline: every Sunday, Bach needed to hand in a piece of organ music. And that’s why if you look up Bach’s catalog, it’s hundreds of pieces long because this guy lived every single week, locking the door, putting the notes down on paper.
And if you can get yourself into that situation, there’s nothing you can’t create.
Jason is from Chico. Many people don’t know it’s in Northern California.
Chico is about 90 miles north of Sacramento.
It’s north of Sacramento?
Yes. 90 miles. It’s a college town and an intersection of a lot of different cultures, which not a lot of college towns are.
It’s an intersection of that year’s college kids who are coming in from the Bay Area, mostly, and some from Southern California. There are also long-term farming families who have been there for 100 years. And there are, especially when I was growing up, there were back-to-the-land hippies.
And then on a rolling basis, all of the college students who came to go to Chico State and then stayed because they liked it. And that was a very middle-aged hippy kind of vibe.
And then there’s families like mine. I was a faculty family. My parents were faculty at the college. My parents came from Midwest. And so there was always an influx of PhDs from all over the country who were setting up shop there.
So you’re in Chico, which I now know is Northern California, above Sacramento.
It’s 90 miles north.
If somebody said “Hollywood” to you in 1985, what would you think of?
You know, the ‘80s and early ‘90s were not great times for Los Angeles. And I think I had a very strong Northern California chauvinism. I wouldn’t have been happy about moving to LA in the ‘80s or ’90s.
What about visiting?
I visited in ‘90.
My first job out of college in ‘94 was at a small publisher in Chico called Moon Publications, not associated with the Unification Church.
If you say so.
Uh, but it was, it was part of that hippie culture that I talked about because a guy wrote a guide book (it was a travel book company) while tripping on acid in Indonesia, and he was looking at the moon and he said, “I’m going to call my company Moon Publication.”
And 20 years later there’s 20 people working there, it’s getting acquired by other publishers and everything.
Kids, take note.
I was an editorial assistant list. Yeah. Um, coming out of college, uh, in, uh, in 94 and I sort of agitated to go to the ABA, the American Booksellers Association Conference in Los Angeles with a hippie who went to college in Chico in the early ’70s and stayed, who is now working at the place.
We stayed in Hollywood at a motel, I want to say, probably on Hollywood Boulevard. And I remember I treated it like a total debauched.
I was just like, “I’m going to a place with no soul. I’m going to a place with only low character.”
This is just going to be a sort of noir Hunter Thompson kind of vibe for the next three days. And that’s kind of how I lived it. And then I left and I didn’t miss it at all.
Is that what your perception was in high school of LA and Hollywood?
Yeah, that it was smoggy. It was ugly. It was covered in concrete. There were no forests, no trees, you couldn’t go fishing. You couldn’t go inner tubing down a cold, cold river, the way you could just outside of Chico.
And you have to also see it in terms of contrasting it with San Francisco. I never even lived there. And yet I fetishize that place as a Northern Californian, as a young adult, as a sort of magical city on the sea where the fog rolled in and where there were Cedar trees.
All of that was an authentic city to me. Los Angeles was not authentic at all to me at that time.
I guess this makes sense why when you left California, you went to New York.
As a young person, New York is an incredible validator of you as, as a grown up. It’s an entire city that you can walk and you can walk into any door in that city.
You can walk into Tiffany’s, you can walk into 21, you can walk through Central Park, you can walk into The Met, you can walk into all these places — these world-class places.
You can walk into an employer. When I moved there later, I walked into Spy Magazine, just walked right in, handed them my resume. Same thing with The New York Times.
New York is about walking through those doors. And that was an experience that I’d never had before. And it made me feel a way that I wanted to capture again.
Through the front door. Whereas in LA everything’s in the back door…
…because that’s where you’re driving in. Yeah.
Which blows my mind because some of the front doors, especially on Wilshire in LA are gorgeous.
They’re amazing,
And yet they’re locked.
So you have children in New York, you raise children in New York, and then you bring those children to this Hunter S. Thompson sin hole to LA, because you were bored of New York?
A couple of things had happened. One, I was now working in entertainment.
And also Los Angeles had gone through a complete renaissance while I was on the east coast.
I mean late ’90s, early 2000s … you could tell me what it was, but things got really great here in a way that I think they probably weren’t in the late ’80s, early ‘90s.
And it was palatable? You could tell the difference?
I could.
This is going to sound obnoxious. We had been coming here for Emmy Weekend for a number of years in a row.
Where did they put you up?
It was funny. We used to complain so much like bitches. The Daily Show flew the entire staff, like 90 people, the tech crew, the camera —
So they rented 90 rooms or whatever, at a place in West Hollywood called The Parc.
And then toward the end they said, “ok now we’re just gonna fly the nominees.” And at that point, the hotels got a lot better and at one point it was, it was Shutters. And another point it was Casa Del Mar.
Now, now the Emmy’s were held in downtown, so they were shuttling you from the beach to downtown, which I guess you can do, it’s just the 10, but it’s still, it’s very generous,
Incredibly generous
Because they could have easily said, ah, you’re going to be at some crappy downtown, well not crappy, but.
Right it’s gonna be at the Hyatt downtown
But compared to Shutters: night and day.
And talking about perceptions, when you’re in New York and you talk to people about LA, they only think about the beach.
Right, I was never privy to the decisions of how those things got decided, but I think Jon Stewart probably wanted to stay by the beach. And he was enough of a democratic person, (small-D democratic) but like, “the staff is going to stay wherever I’m staying.”
That was a thing that I realized later, oh, not every TV star puts his staff up in the same hotel that he stays in. I had actually had a few examples of “oh, they’re not even on the same side of town as the rest of us.”
Which is to his credit.
Falling in Love with Hollywood
Were you were telling me that one of the issues when you moved from Los Feliz to Hollywood was people rent Airbnbs and throw parties and
I’m actually lucky because I’m telling those stories second-hand. We don’t actually have an Airbnb problem in our immediate hood.
Well, but that might’ve been COVID?
But it has even before COVID, it hadn’t happened. Like it had happened in a way that we were hearing about.
And the issue was that people would rent, Airbnbs, have big parties and the, the music would vibrate through the canyons —
And clog up the streets because the canyons are roughly one car wide to drive through.
Let’s say you’re a 28 year-old miscreant, like we used to be, and you want to throw a party, … if you put together a little bit of money you could have a house with a view with a deck, with a pool.
You get five people chipping in, maybe you put 1-2 thousand bucks for a weekend.
You’re balling.
You’re balling and you invite 100 people. And of course they’re going to come. And of course they’re going to treat it like they’re on vacation. And meanwhile there’s a family next door who are like, “Tina and Tony used to live there. They were pretty cool. They had a dog. But I guess this is this, this is what we got now.”
So when people say, “okay, this is my dream. I want to be a writer. I want to live in New York. Then I want to move to the Hollywood Hills. And I want to raise my family in the Hollywood Hills. Everything’s going to be great. And if I can only do A, B and C and I get there, it’s all gravy.
But as soon as you lean back in that couch, you hear Pitbull and the Fireball song all night.
Yeah. Unlivable, totally unacceptable. Totally.
And I know — I am a close enough follower of you on social media to know that you have a very short fuse for city dwellers who complained about city life,
But I also don’t have a baby that’s trying to sleep. I have a very different life than you. So I’m grateful that there are other people who put me back into check and say, “Hey, not all of us can sleep until noon…”
In fact, none of us can, you should check that.
But that’s what I actually appreciate about life: the dreams that we had as teenagers, especially teenage boys and the harsh realities of what life is.
Even when we hit that home run, what happens? “Oh, you didn’t step on first.”
Okay. So outside of that little Airbnb world, Mr. Northern Californian has now lived in LA for a number of years, raising children. One of your kids is now old enough to start working a part-time summer job.
So how do you feel about living in Hollywood now?
I love it. I would happily live here the rest of my life. Absolutely love it.
Hollywood is, is by far, the most beautiful neighborhood in Los Angeles.
This is not at all what I was expecting.
Oh, really? I mean, I have fantasies about having some boat that I can live on or something, but like, in terms of practical, real life, like where do I see myself? If we could stay in our house until they wheel me out in some kind of stretcher, I would be thrilled.
I’m surprised because I felt like you were happy in New York. And it sounds like you loved your childhood in Chico. And we loved living in Santa Barbara.
All of those places are very different than Hollywood: Santa Barbara, Chico San Diego (for your wife,) Upper West Side.
Ain’t no Upper West Side in Hollywood.
Yeah it’s different.
And so for you to love it, the way that it seems like you do — shout out to Hollywood
Hollywood is the most beautiful neighborhood in Los Angeles because it’s a little bit elevated. There’s a gradient to the streets. You can look down Vine and it’s actually looking down Vine.
There is a Riviera kind of feel to it.
I mean, the whole thing that’s special about Los Angeles is that its man-made parts are beautiful and the nature and the natural setting is beautiful. And I think it’s really at its best combination in Hollywood
The Amazing Beef Squad Never Say Die
So now you’re written The Amazing Beef Squad Never Say Die. I don’t want to call it a children’s book — young adult, YA?
It’s actually called Middle-Grade which, age-wise is one step below Young Adult.
So like, so like the first Harry Potter book was Middle Grade and the later ones were Young Adult.
Middle Grade is a really booming market right now and it’s possible to sell a book on a proposal, which you can’t always do. That’s one of the reasons I wrote it.
And you knew you had a story in ya and it wasn’t going to be hard to get out.
Um, It didn’t quite know how it was going to get to the end. They talk about Act Two Problems in writing …
I don’t know anything about that.
Well the cliche complaint of a writer is, “I’m having problems in Act Two,” because that’s where the hardest choices you have to make are and the most creative decisions — most creative solutions you need to come up with are in.
It’s that place where it’s not the beginning where Luke Skywalker is a moisture farmer on Tatooine and he longs for something more exciting. And it’s not the end where a bunch of fighters blow up the Death Star.
You knew that when you started, well, “we’re going to start here and we’re going to end here,” but what’s the Act Two in the middle?
How are you going to turn this into a story that feels like… you’re absolutely certain the heroes are gonna fail? That’s what Act Two is for. It’s to let the heroes fail at their task and to make the viewer or the reader feel like that is a final failure.
It’s over. Their dreams are dashed.
They’re in the garbage disposal—
That’s literally like, there, like there is a on Dan Harmon’s hero’s circle of like eight different stations.
And developed that from Joseph Campbell, which is the same thing that George Lucas was reading when he did Star Wars. And so if you track it like minute-by-minute, the garbage disposal in Star Wars is at exactly the point where it’s supposed to be on that hero’s journey.
But that’s hard. Even with tools as powerful as Joseph Campbell and all that, it’s hard to get through Act Two. So I wasn’t totally sure how I was going to get through it
But I knew there was a… a worldview that these characters, these 13 year-old boys had about their surroundings, about their world, and about the way they move through it, that I wanted to pursue.
You know, that surprises me, that Act Two would be the struggle for you because you are a comedic genius. And we all know that most, very funny people are also very in touch with their dark side and isn’t Act Two the dark side?
Yeah. First of all, thank you, that’s B.S., etc.
It’s not so much the decision to go into the dark side, it’s what’s going to happen there. And what are the mechanics of it that are gonna make it feel like a final failure that actually is a portal into a chance for redemption in Act Three?
It’s not so much a matter of your sensibility as your imagination. At some point it becomes almost a mechanical force.
The story becomes almost mechanical that a certain thing has to happen for a certain other thing to happen.
Would you agree that writing in Hollywood is like “The Player,” in that the writers are super important, yet the studio has their agenda. And even if you’re an idealistic writer and you want these unknowns to be in your movie, it’s still going to be Bruce Wilson and Julia Roberts.
Short answer, of course. It’s a business.
One of the key phrases is “they don’t call it, show friends, they call it show business.”
I’ve been really lucky to work really consistently with a lot of people who I do call friends. And I think that at a certain level, especially if you can work on a hit like The Daily Show where you’re really coming into work just to work, just to create. There’s no wheeling or dealing in that atmosphere.
And John Stewart should be commended for keeping that kind of vibe out of that building.
And the people who are left — it honestly felt a lot like, like the Daily Nexus, our college newspaper, where people are just coming in, trying to make something that they’re proud of.
Um, and when you’re doing that, it doesn’t feel at all like a cynical movie. It feels like exactly what it is, which is people coming together to create something in just the most natural kind of way.
In the same way that we’ve put together shows in front of the fire and put together ceremony. You’re bringing all of that to bear on something. And, yeah, you need to get paid for it because you’re trying to make a living. And you’re trying to take care of your career at the same time.
But there really are sweet spots where you are just working and that’s what I’m here for.
And there are people who are here for the power, who are there trying to set themselves up as some kind of power broker… and that’s not what draws me.
As long as it’s expensive to create these things, then those people will always be there. Someone needs to have control of the budget.
But there are enough episodes of just pure joy, full creation for me that that’s what the business is about for me.
Pick up Amazing Beef Squad Never Say Die at your local bookseller on online at these fine establishments.
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