Talking to New ‘Daily Show’ Head Writer Elliott Kalan

Over the last decade, comedy writer Elliott Kalan has risen up the Daily Show ranks, starting as an intern before becoming a production assistant then a segment producer then a writer until, last month, being made the show’s head writer. Kalan took over for Tim Carvell, who left to be the showrunner for John Oliver’s new HBO show, Last Week Tonight. I recently had the chance to talk to Kalan about what the new job entails, how The Daily Show’s writers’ room works, and doing standup.

When did you officially start as head writer?

This is my third week, so my official start date was January 20th. We were on break until January 6th, and I would have started then, but I had a baby on the 1st so I was actually on paternity leave for the first two show weeks of this year. So it’s really just been a short amount of time that I’ve been the head writer.

Congratulations on the baby, by the way!

Thank you very much! I’m very excited about it. January has been a very busy, exciting, and crazy month. It started with a baby on the very first day of the year, two weeks of just being at home with my wife and my son, and right on into a new job involving a whole set of new skills that I’m still developing. Hopefully, February will be very sedate. I would like for nothing to happen for the entire month of February. And if nothing happens in March, I’ll be okay with that too.

How long were you groomed for the job of head writer? When did you find out you had the job?

They told me in early December, but I couldn’t tell anyone until the news was public to the staff about a week later. The same thing happened, but more so, when I was made a writer on the show. They said, “We’re gonna hire you to replace this other writer, Rachel Axler, who’s leaving. We’re gonna make you a writer on the show, but we want to announce it at this specific time, so we’d appreciate it if you didn’t tell anybody for a little bit.” So I had to just contain this information that would change my relationship with my co-workers, for a while. I had to hold onto it for weeks and weeks and weeks. In the end it was worth it, because when they announced to the whole staff that I’d be a writer it was one of the greatest moments of my life. Still, I was glad I didn’t have another long secret waiting period like that this time.

What was the transition process like? What was it like learning how to do this job, and what are the new responsibilities you have?

The job has a very different set of goals and responsibilities and objectives and skills. As a writer, I felt like it was my job mainly to generate ideas for material, and then when I was on an assignment, to produce jokes with a point of view that were funny, sharp, fit the voice of the show, and were as interesting as possible. As head writer, that’s still very much a part of it, but at the same time, there are a lot of skills like communication between departments, personnel management, interaction with show management to a much greater degree than I’d been involved with before; things that were never a part of the job as a writer.

As a writer, you focused on the writing and your place in it, and as a head writer, your eye is so much more on ‘How is everyone working together? Is this department integrated with the rest of the show properly? How can we make sure all the writers are doing the best work that they can and the work that’s most appropriate to the show and serves the show the best and serves Jon the best?’ It’s a widening of scope outside of myself, in a way. It’s interesting because when you get you get married, your point of view becomes ‘What’s best for us?’ rather than ‘What’s best for me?’ With having a son, it’s like, ‘What’s best for my family?’ Now, I’m responsible for this group of three people and not just for myself. It was a similar transition going from writer to head writer. You become responsible for more than just yourself. It’s similar skills to what I’m using in taking care of a baby, which sounds like I’m comparing comedy writers to newborns, which is not the most flattering of comparisons - but there is definitely a feeling of ‘Okay, now I’m responsible for lots of peoples’ work and not just for myself.’

I’m enjoying the job a lot. I like being challenged by it. The reason you want to move up in an organization is so that you’re always being challenged, you’re always being presented with new things, new ways to grow the skills you have, ways to get new skills, and new opportunities and problems, and things that you haven’t encountered before. I’m the kind of person who, if I do the same thing for too long, then I start to get frustrated. Getting this job has been a godsend because there’s the excitement of being challenged by a new situation that you haven’t been in for. I come home at the end of the day and I’m like, “That was great! I really did a lot of new stuff today and I’m interacting with people in a new way.” It’s really exciting.

Being that type of person who always wants to learn new stuff, do you ever have the fear that you’ll bite off more than you can chew at some point?

It’s possible. I feel like anyone who has any ambition worries that eventually you’ll reach your level of competence and then accidentally go past it. But the only way to find out how competent you are is to keep moving. Eventually, you’ll get to a level where, if you fail at it, you just fall back a little bit. If you’re looking at a job straight-on, and you’re thinking, “What skills do I need for this? How do I best do this job? How do I put 100% of myself and 100% of my energy into it?”, then it’s hard to bite off more than you can chew because you’re looking at it soberly and saying to yourself, not “What can I handle?” but “What do I need to gain to handle this situation?”

The Daily Show has a lot of different segments with different styles. What parts of the show are you best at, and what parts are you not as good at?

Even though I come from a sketch background I think I’m not quite as good with correspondent chats, which is weird because essentially they’re dialogue sketches that rely on establishing a premise, heightening it, and developing it into a full comedic idea. But for whatever reason, I feel like I’m not quite as sharp on that as I am with writing a headline where Jon is making a case for something and is interacting with video footage and introducing graphic elements, that kind of thing.

Are there writers that specialize in each type of segment on the show?

Not really. Everyone does everything. Everyone on the writing staff is really good at being available for any type of assignment. There’s some shows where they differentiate between, say, monologue writers and sketch writers, but here, you could be on a headline one day, you could be assisting on a field piece the next day, you could be working on interview questions. The writers are all jacks of all trades, so there’s not really that kind of specialization. Occasionally, there will be a particular writer who has a specific knowledge set that comes in handy, so they’ll be put on the kinds of headlines that take advantage of that, but otherwise, we don’t divide everybody up that way.

Will John Oliver’s new HBO show change how The Daily Show operates in any way?

Nope, but it’ll change how my Tivo operates, in that I’ll need to drop a Sunday show to make room for it. So long, Masterpiece Classic!

You’re used on camera on The Daily Show a fair amount. Do you enjoy acting?

I used to be [used on camera a lot]. I haven’t been in a while. I liked it a lot. I’m a big attention hog, and I like to have people looking at me and listening to me, so whenever they would write me into the show, I would be like, “Great! I’m in. That sounds fantastic.” But I’ve had my run. It’s time for the younger members of the staff to get their time on camera. And I was never going to make a career out of on camera performance, I don’t think. That was always kind of a lark that I was excited about, but I never thought in my head, ‘Oh, this is what I’ll do then. I’ll become a TV actor. If I get enough of these performances on my reel, then I can start going out for sitcoms.’ I have no interest in doing that.

But that was fun. They were always a matter of someone calling me in the middle of the day and saying, “You know you’re in the show tonight, right?” And I’d say, “Nope.” And they’d say, “Okay, well, you’re playing a hot dog vendor or a child”, and I’d be like, “Well, I’m glad that I shaved today.”

Do you still do standup?

Occasionally. It’s something I enjoy a lot, and I wish I had the discipline and the sticktoitiveness and the motivation to make a real go at it. But it takes so much effort and time and energy, and it’s really hard grueling work. I really admire anyone who makes a career in standup but also anyone who does it while having another job. There are writers on this show who do standup much more often, like J.R. Havlan and Matt Koff. I really admire that they can put the energy and the time into it because when it comes to standup, I’m pretty lazy. I love performing it, but it takes maximum effort to become a really good standup and I feel like I just don’t have what it takes to push myself to that level.

I was lucky enough last year, I got to go with some other Daily Show people on this USO Tour of five different Army and Air Force bases in Afghanistan and Kyrgyzstan. It was really exciting. Meeting the people there was really amazing. It was a real once-in-a-lifetime opportunity. I’m glad that I’m good enough that I could do that, but there’s no way I’m good enough to go semi-pro. I’m a standup dilettante is what it comes down to. I don’t have the drive to go out two or three nights a week, doing any show I can, looking for time anywhere I can, just pounding the pavement and grinding that out. Especially now that I have a baby.

Standup feels like when a guy is in a band with some friends and they play shows at bars every now and they’re like, “Yeah, you know what? We could get good at this if we really worked hard at it,” but then life just gets in the way so the guy just looks at his guitar in his closet every now and then like, “I was in a band once.” That’s what standup feels like to me, but much less sad than that.

I mean, having a baby and the head writer job makes it harder. It’d probably be easier to do more standup if you were a less veteran writer who’s single or something.

Yeah, but there’s a real “grass is always greener” thing about it. I’ve been a fan of standup since I was a kid. When I was a kid, there were so many standup shows on TV. There was the MTV ½ Hour Comedy Hour, Stand-Up Spotlight on VH1, HBO did so much standup. There was so much standup stuff on television when I was a kid, and I’d watch all of it.

When I go to see standup infrequently, like if a friend of mine is performing, I’ll go try to see them, and when I’m watching the standups, there’s this real “grass is always greener” thing of “Oh man, I wish I could do that. If I had the freedom to just do standup shows and I didn’t have my day job and I’d just do my standup set.” I know that to them, they’re like, “I’ll keep doing this until I get a TV writing job, and then everything will be set and I won’t have to do standup anymore. I’ll just do it when I want to.” It’s like the guy on the stage always wants to be the guy with a job and the guy with a job always wants to be the guy on stage, at least as far as my experience goes. Or if I would go to friends’ sketch shows and they would be on the bill with another sketch group that I didn’t know and that sketch group would have packed the house with like 65 people or something and the audience would be going crazy, I’d be like, “Man, I wish I could be doing that! Oh well, but I can’t because of my TV writing job. I wish I didn’t have this stupid television job so I could do more sketch performing in black box basement theaters.” But the human brain is stupid and thinks crazy things. Basically, whatever another person is doing looks cooler than what you are doing right now.

Though to be completely clear, objectively nothing is cooler than what I’m doing right now.

Talking to New ‘Daily Show’ Head Writer Elliott Kalan