"Daily Show" Writer Jason Ross On Writing For Free and Breaking Into Comedy

Jason Ross working the comedy machinery at the Daily Show.Since 2002, Jason Ross (@jasonjross on Twitter) has been a writer for “The Daily Show With Jon Stewart,” where his team has won a half-dozen Emmy Awards for outstanding writing and produced the best-selling America: The Book and Earth: The Book.

Jason Ross: Here I am.

Ken Layne: Hello, sir! I’m in the middle of the greatest consumer survey in human history.

Jason: That is a fairly low bar to clear.

Ken: Disneyland is building Star Wars Land. This will make Disneyland much more tolerable for me:

Which of the following Star Wars locations would you be especially interested in visiting at the Disneyland Resort? Please select all that apply. Move your mouse over each to view location.

Jason: OK. That’s worth moving a mouse over each location for…

Ken: Anyway, there’s a lot of talk these days about “writing for free” and whether that’s a new paradigm of exploitation and etc., and I thought we could talk about that in the context of becoming a professional comedy writer. But first, we must introduce you!

Jason: Should I … ? OK. My name is Jason Ross and I am a writer for “The Daily Show with Jon Stewart.” Is that … ?

Ken: Shoe size. They can figure out the rest from “shoe size.” No, that is fine. Now, you were produced by the same excellent environment that produces Sierra Nevada Pale Ale, is that right?

Jason: I hail from Chico, California, which produces Sierra Nevada brews of all types. Also lots of almonds. And marijuana. And rice.

Ken: A good vegetarian diet. So between college and about 1998 when I remember hearing that you were embarking upon a comedy career, what did you do?

Jason: I came out of UCSB and the student paper there, the Daily Nexus. After that, I went up in the hills to write my novel and learn to fly fish. Let’s just say the fishing went a lot better than the writing. It was time for a job and soon I was working at Chico’s alt weekly, the News & Review. I worked there as a writer and editor for three-plus years and decided it was time to move to New York. I had the idea of becoming a magazine writer but quickly became discouraged at how difficult and uncertain that life would be. If life was going to be so difficult and uncertain, I might as well feel that way in pursuit of something incredibly fun and rewarding. I became a comedy writer. In my own mind. You and Charlie [Hornberger, co-editor of Tabloid.net] were a couple of the first people to know.

Ken: And we were having fun, but the money was a bit of a struggle at that point.

Jason: Quite.

Ken: There were some magazine writers from that crowd, too, and all the ones I remember were usually broke and eventually did something else.

Jason: Like shoot themselves in the back of the mouth?

Ken: We try not to talk about the thousands of suicides, but probably. The Onion existed, and there was Mad Magazine on the newsstand… National Lampoon was gone, not a lot in the way of humor outlets besides TV. But there was the Web, pretty much open to whatever anybody wanted to do to it.

Jason: Yeah, McSweeney’s was up and running by then.

Ken: Around the time I could no longer live on cigarettes and fog, I left San Francisco and Tabloid and you began writing a lot of insane stuff, it seemed like three or four pieces a week for us. Probably one of the most absurd things we ever posted was a fake interview you did with something called “the Man Cow,” I think?

Jason: Yeah, I later found out that was the name of a shock jock. I was spending some savings, writing a “News Radio” spec script and shooting of stuff to Tabloid when the ideas struck me. (My Man Cow was the product of GM farming.)

Ken: Haha, I wrongly remember that as a deliberate parody of that shock jock with a similar name (cow man?) who had just caused some huge ruckus at a California airport by doing a Bill Clinton stunt… getting a haircut on the runway, which I think ended up being a Fox News myth anyway, that Clinton had done that. This is just one of many examples of comedy being magic.

Jason: Some of my favorite jokes as a kid were Steve Martin and Johnny Carson jokes I don’t get (because I was a kid) so they just sounded like nonsense to me.

Ken: Oh me too. I thought “Winslow Boner” was the funniest thing I’d ever read, in Steve Martin’s book Cruel Shoes, and years later in art class I learn that it was about Winslow Homer.

Jason: That is DEFINITELY funnier without the referent.

Ken: I also had never read the “Gift of the Magi,” so the story “Cruel Shoes” was just completely out of the blue and fantastic.

Jason: Oh god. I never even made the connection…

But they were clips! (I don’t know if people still say “clips.”) And with this portfolio, along with a winning personality, you were able to get a low-paying job at a website.

Ken: It’s probably a good idea for little kids who like comedy to just read and listen to as much as possible, get a head full of Richard Pryor race humor and George Carlin drug jokes and then go freak out the 25-year-old teacher-squares at elementary school. Anyway, in my own mind. we never paid you at Tabloid. We didn’t pay anyone. How did you feel about this sexploitation?

Jason: I assumed you just lost the invoice.

Ken: We smoked the invoice. (That’s drug humor, if you’re reading this to your kids.)

Jason: Kid: “You mean the way we smoke gouda?”

Ken: :(

Jason: Those pieces were my first attempts at published humor. Having them accepted and presented to the world was all I wanted. Also, I knew that you and Charlie weren’t raking it in, so it wasn’t like I was actually being financially exploited.

Ken: I dreamed of paying people. Actually had dreams about that. I remember people saying at the time, “Oh, don’t you want to sell Tabloid.net and get rich” and I would think, “No, I just want a job doing this.”

Jason: Wrong answer, bro.

Ken: The people asking also didn’t have any money. But, I am fine with the eventual fate of everything. Which is the Void.

Jason: BRING ON THE VOID.

Ken: It’s coming, on its own schedule. Now where else did you get these early comedy pieces published?

Jason: I had two pieces on McSweeneys.net and… and… That would be about it. They didn’t pay either.

Ken: But they were clips! (I don’t know if people still say “clips.”) And with this portfolio, along with a winning personality, you were able to get a low-paying job at a website.

Jason: No bullshit: In 2000, I was working for an ad agency, miserable, when I spotted an ad for a comedy writer for a comedy website startup. One of the job requirements was experience with online comedy. I wrote a brief introduction email and then pasted in those URLs. They were my entire resume. And I got the job!

Ken: Incredible. We should say that in 2000, websites were the “mail room” of most media companies.

Jason: This one was going to be HUGE. It was called iCast. It belonged to that giant incubator in Boston… ICBM?… That can’t be it.

Ken: Ah, a dot-com startup! Okay, different scene altogether. Because at this point, newspaper websites usually weren’t even run from the same building as the “real” paper. They were in … well, a real example: Ed Mazza, who did a lot of Tabloid stuff, got hired at (I think?) the New York Daily News website, and it was a closet. A utility closet. Maybe that wasn’t even Ed, though, and it might’ve been a different paper, or city.

Jason: This had like four sections: film, music, comedy and…
wait for it… MAGIC!!!

Ken: MAGIC???

Jason: I saw a PowerPoint headline that said this: “We can WIN in magic”

Ken: Like, performance magic? Or secret word magic?

Jason: They signed some kind of deal with David Blaine, but I never saw how they planned to make magic online. Look, it’s a GIF… but it’s MOOOOOOVING!

Ken: I will pitch this to The Awl or Gawker or something… a new site, about stage magicians. The majesty, the costumes. Or whatever David Blaine does, magic by the subway ticket machine. Toilet magic.

Jason: The startup never launched, so it all died in utero. But I distinctly remember a screensaver of the Last Supper, except everybody in the picture is just pigging out. Very funny, not my idea. The boss there was John Wooden, who made Chickenhead. It was silly non-sequitur stuff, mostly. So that job lasted seven weeks, but then the editor from that site, Todd Jackson, went on to edit Comedy Central’s website, and a few months later he hired me.

Ken: Okay, so here is the secret ingredient: The one guy from the failed startup brings some of his people to his next job.

Jason: Yep.

Ken: At that time, Comedy Central didn’t have much going on online, is that right? (This will be instructive for the terrible 20-somethings who assume we always watched teevee shows on the computer.)

Jason: It was much more primitive than today. There was no video server for recent episodes. Most of the job was writing promotional “touts” for upcoming shows. Those had to change every day. But there was, for a few months, a dream that this little office of people were going to be a source of original online comedy content. Then they fired that VP and we just became a promotional arm of the network.

Ken: RIGHT, that was the idea when you started, I remember this now: Original web comedy for the Comedy Central channel’s website, a sort of farm team.

Jason: Well, “farm team” is a little hopeful. It’s not like people were getting called up to work at the shows on a regular basis.

Ken: But it was pretty new, the whole “websites as an adjunct to other mediums,” so there must have been some hope that you and your coworkers would be doing comedy for the bigger audience at some point?

Jason: We were proud of our work (when it was good), and I’d guess that maybe a quarter of the staff there had pretensions of doing “real” comedy some day. Others seemed content to be Web producers, graphic designers, etc.

Ken: How did you get from that promotional website office to the writer’s room on the “Daily Show”?

Jason: Practice!

Ken: The answer is “Google maps.”

Jason: I actually might have gotten this job without the ComedyCentral.com connection, because I was friendly by that time with the head writer on the show, who invited me to write a submission when they were hiring. At this point, I’d been an aspiring comedy writer for five years, and I’d done a little bit of stand-up and a lot of hanging-on to other, more successful comedy people.

Ken: So this is the New York comedy club scene of… early 2000s.

Jason: Yeah. Though I may have never been to an actual comedy club. It was happening in bars downtown, at the UCB theater, which at that point was a tiny garret off Union Square.

Ken: At some point between 2000 and 2004, “The Daily Show” became a huge thing. I remember being at… Craig Kilborn’s “Late Late Show”? I think so, yes, our friends in the band Tsar were doing the show and I went along, maybe summer of 2000. And I met your current boss, Jon Stewart, just saying hi on the smoking patio at CBS in Los Angeles—I assume he was doing the “Daily Show” in Los Angeles that week, or maybe he was taping for Kilborn’s show because Kilborn used to host “Daily Show.” I have no idea, really. But nobody bothered him. Then by the time of the 2004 presidential election, people would mob him at the conventions, etc. And this is the era when you came in, right? By “this,” I mean during this transition from smart cable comedy show to national phenomenon.

Jason: Correlation isn’t always causation, but in this case ….

Ken: You did this. Through MAGIC.

Jason: I can WIN in magic! I came on in 2002. The show had already made its mark in the 2000 election but Jon’s vision for it kept getting sharper and more elegant as he found his footing.

Ken: From my terminally underemployed comedy writer friends in Los Angeles, I’ve heard there’s this pyramid of pay, from staff on a hit network show to a mid-season replacement writer on a cable reality thing that’s not even supposed to be scripted, etc. Where was the “Daily Show” in 2002 on that scale, and where would you guess it is today?

But do work for free if you see a clear path from that work to a better situation down the road. Comedy’s a perverse world where 90% of the people work for peanuts and 10% do embarrassingly well.

Jason: It was always better than what a reality writer makes, but when I started it was somewhat less than comparable late-night shows. (In your hierarchy, late-night writers are probably right in the middle—less than sitcom writers, more than most other TV employees.) When the show became a Writers Guild of America signatory in 2006, I got about a 50% raise. Currently, we’re probably in the middle of the pack, pay-wise.

Ken: Oh so you’re a fancy union member now. How’s caviar taste, Jason?

Jason: Salty.

Ken: You know where almost all caviar comes from now? Salmon farms in the Sierra Nevada foothills. Not so fancy since we destroyed all the wild salmon rivers. Here is what I think is the best part of your job: You won’t ever get canceled. Sure, Jon Stewart will eventually be replaced by an 88-year-old Jay Leno, but the show is not going anywhere as long as there are idiots making the news.

Jason: Yeah, Jon will never be canceled because Jon will never phone in a single day. And I thought caviar was sturgeon roe.

Ken: That is the traditional definition: wild sturgeon roe from the Caspian and Black Sea. But we killed most of the wild sturgeon long ago.

Jason: They had it coming.

Ken: Now you are probably buying farmed salmon eggs, or even trout eggs. There’s one wild sturgeon watershed full of caviar that still exists, in Iran I think, and we’ll probably nuke that.

Jason: Not the Columbia? There are still guys who catch them in the Sacramento, just outside of Chico. But maybe you’re talking about a harvestable fishery.

Ken: The Columbia River is all dammed up, but yeah, there is restoration going on. And even some caviar poaching!

Jason: Now THIS is what I want to talk about.

Ken: This is what happens when you get a fly fisherman and an extremist environmentalist talking about comedy salaries.

Jason: Every fucking time…

Ken: Here is something I wrote about caviar not long ago. I’m giving you the Google cache because apparently The Awl is being hacked right now. And I don’t want to shut down the “Daily Show” with malware.

Jason: Congratulations!

After accepting an Emmy, you must dine with it every day, while dressed in formal wear, until death.

Ken: You have an Emmy, or actually many Emmy awards! I saw a Bob Dylan show a few years ago and he had his Oscar on his guitar amp. Where do you keep your golden idol?

Jason: I don’t have an amp. They sit atop a bookcase in our living room.

Ken: I thought you were doing pretty well for yourself, and you don’t even have an amp. Well at least you have something to put on a bookcase.

Jason: I can afford an amp. I can’t afford the extra room where my amp goes.

Ken: I forgot to ask if you let your kids play with your Emmy. But you keep it on a bookshelf, which is where we put things the kids can never, ever touch or even think about. So let’s wrap this up so you can go back to your 10,000-square-foot Williamsburg penthouse and write comedy, remotely—

Jason: Wrong, DEFINITELY wrong, and wrong.

Ken: Everyone in New York has a 10,000 foot penthouse, I know this. What is the most fun, most rewarding part of being on that staff?

Jason: Two meetings a day of 20-odd funny people where it’s pretty much everyone’s job to try to make each other laugh. Plus catered lunch. Now about working for free ….

Ken: Yes! That is our topic, or it was?

Jason: I’d say in general, don’t work for free if it’s for a big company that’s making—or could make—real money off your work. Think about the bitterness of the Huffington Post bloggers who watched their “can’t-pay-you” boss sell the company for $315 million. But do work for free if you see a clear path from that work to a better situation down the road. Comedy’s a perverse world where 90% of the people work for peanuts and 10% do embarrassingly well. If you want to break in, you have to suffer. But at least you know which direction you’re aiming.

Ken: That is wise. Whenever there’s a system in place for people working for free, like a pen where they’re kept and expected to stay while producing free intellectual property, probably you don’t stay around there beyond a summer internship while you’re in school. Because I learned from watching The Ten Commandments that that’s morally wrong, and you should rise up, etc.

Jason: Speaking of a ruined watershed…

Ken: Filled with Biblical slave blood, so bad for wetlands. I will link to your CSU Chico speech that I found last week, too, because it is very instructive and thoughtful. Oh, and plug your next standup or any project, I forgot I am doing a TV-related thing here.

Jason: No plug.

Ken: Okay! Well, thank you for this!

Jason: Thanks, Ken. It was fun. When can I expect the check? See what I did there????

Ken: Right away! Should say “The Awl” on the envelope, or “OPEN AT ONCE, Department of the Treasury: Internal Revenue Service,” etc.

Jason: I just got that last week! You guys work fast.


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