From Letterman to Wilmore: Inside Network and Cable Late Night Shows with Lee Ellenberg

Lee Ellenberg knew he wanted to write for David Letterman when he was a teenager. After watching Letterman’s Late Night show, Ellenberg worked his way up the comedy ladder, starting as a Late Show Page, soon becoming a writer’s assistant, and eventually landing his dream job as a Letterman staff writer. After Letterman’s retirement in 2015, Ellenberg ventured out into the unpredictable world of sitcom writing and now finds himself back in late night, writing politically-geared humor for The Nightly Show with Larry Wilmore. I spoke with Ellenberg about working for Letterman, developing a pilot with Rob Reiner, and the difference between a class clown and a comedy writer.

What was it like changing jobs after two decades with Letterman?

It really felt like my first day of school. It doesn’t matter how old you are that feeling is still so fresh in your mind. The night before you’re nervous. But I was so excited to do it – I’d been at Letterman for so long. So all the negative things you associate with the first day of school or the first day of a new job, I was craving. I embraced all of that. I embraced the uncertainty. I couldn’t wait to have a different commute to work. I was excited to walk through a different door and be greeted by different faces and have a different office and different computer. I knew nothing and I was so excited about knowing nothing. I was just so happy to learn a different routine and see how this group of people put together a show, which is so vastly different than the way we did it at Letterman.

What’s different about working for Late Show and The Nightly Show?

It feels like I’ve gone from working for this multinational corporation to this independently owned business. It felt like we had an army of people at Letterman and here we have a smaller group and they work twice as hard and in many ways are able to produce a lot more. It’s a much leaner operation. Here everyone is encouraged to go to rehearsal. To see the host run through all the work the writers have done is very informative. You feel like you’re playing a larger role. At Letterman you were really responsible for producing the piece you were in charge of that day. At Wilmore, you aren’t. You write the script and then the editors, the graphic artists, the talent department, and producers produce the scripts without you. Working so closely with the host you just feel more part of the system. It feels nice. It’s also a much more narrative kind of show. It’s almost like crafting a very long op-ed piece for the newspaper, but it has to contain multimedia elements and it has to be funny. The writing process here is much more labor intensive.

What type of things will you go over with Larry Wilmore?

Basically he sits in a room with the head writer, the showrunner, the writer’s assistant, and the script supervisor and he runs through the entire show. After rehearsal there’s a rewrite. Then there’s another rewrite session where Larry goes through the show again. He literally goes through every word of the script, from front to back in order to put it in his own voice. It’s a fascinating process to watch.

The Nightly Show is more political than Letterman’s Late Show. How do you approach writing comedy with a political angle?

With Letterman it was always “what’s funny?” The writers came in every morning and we thought, “We have an hour to come up with the day’s comedy, what’s funny?” And if George W. Bush choked on a pretzel, that’s funny. We weren’t that interested in policy. We were interested in fuckups. The only agenda we served was Dave’s and that was: “Give me a funny show.”

With Larry, it is political. And he’s not interested in taking a liberal or conservative side. He’s really not. It’s more about “can we approach this issue from an angle no one else is talking about?” And that’s the challenge. Today we were talking about the Olympics in Rio and one writer came up with the point that the media is making a big deal about the hardships the athletes have to deal with while in Brazil, but these same hardships are what people in Brazil have to face on a daily basis. His point was “at some point these athletes are going to go home and the citizens of Brazil will still be dealing with these horrific conditions.” Nobody is talking about that.

It seems like you’re doing double the work, finding a unique angle and then having to make it funny.

We’re constantly being told “It’s not just about making a point, it’s about doing it in a way that’s funny and also sensitive.” The one thing I love about this show is we’re willing to address issues that we would never touch at Late Show. We just wouldn’t. There was always a fear of offending people. Here, we’re not afraid to wade into a topic. That pitch about Rio, you can almost see, not that’s it funny that people are dealing with horrific issues, but it’s the absurdity that makes that funny. If you’re a comedy writer, you should be able to make anything funny. That’s your job. I find the challenge is reading a news story and being able to find that interesting take. A writer from our show, Mike Pielocik, did a deep dive into the Flint water crisis. It’s fantastic. It’s so informative. The show did it in such an amusing way, but in no way did the story make the light of the situation or find humor in the hardships these people face. It’s more about the absurdity of callous politicians.

There are plenty of late night shows now – Last Week TonightFull Frontal, and Late Night – tackling politics and policy. How much of an effect do you feel like these shows are having in actually sparking change?

I do think there is an effect. Back in the day you had shows like 60 Minutes and Meet the Press that were trying to directly question those in power. I think people like Jon Stewart and Stephen Colbert hit upon this tremendous formula that coincided with the rise of the Internet and became the voice of the younger generation. You heard politicians say: “I know if I say this I’ll wind up on Jon Stewart tomorrow.” They were just doing incredible shows. There was something very cathartic about seeing these two guys call out the people in power. Now that Stewart doesn’t do his show anymore and Colbert is at Late Show you have Samantha Bee and John Oliver doing it just as well. And people like Seth Meyers, who is doing a more traditional late night show, which I love, but he too is an important figure. There used to be a time where people used to think it was a bad thing that young people were getting their news from the Daily Show. I don’t think that’s such a bad thing anymore. It’s an interesting time to be working in late night television.

What was it like writing for Letterman during his last shows?

I felt like I did in the last months of college. You just knew something great was ending. And I’m not just talking about the show. I’m talking that chapter in my life. College was four years. This was 20. And for several people it was close to 30. Just knowing that I was never going to see these people on a daily basis again was sad. But it was also freeing. Unfortunately, we dealt with these conflicting emotions in the most immature manner conceivable. For some reason, we had these twenty rubber balls sitting around the conference room and, during those last weeks, we would shut off the light and throw them at each other as hard as we could for about an hour. We called it “murderball.” Every night someone took one directly to the eye socket. Our immaturity notwithstanding, those last few weeks were special. It felt nice being able to help guide that ship into dock. If that’s even an analogy. I don’t know anything about boats.

Dave handled the last show perfectly. We always knew we were working for an icon and he did it with such grace and class. All the writers just sat there watching the screen. It was dead silence and in that moment we were just really proud. I always said my worst day there was still pretty great. But I was also ready to move on.

So what did you do directly after leaving the show?

The first few months after the show ended me and Jeremy [Weiner] did a few projects together. We went to L.A. to try and get a couple of things off the ground.

A TV Series?

Yeah, we pitched a pilot. We didn’t sell it. I actually wrote a pilot for Rob Reiner. I was hired by him and we had a couple of meetings about what we wanted to do. I went on a research trip for it. And after all this time and work I wrote a first draft and I have not heard from him since handing it in four months ago. Which is usually a really good sign. It’s usually a sign that he really loved my first draft.

Is that true?

Well that’s what I’m telling myself. It’s probably a terrible sign. Basically I’m telling my mother, “The longer you don’t hear from someone, the more they love it.” Look, if he’s moved on from it it’s more than fine. It was exciting working with him for a few months and he could not have been a nicer person to work with. And to be able to sit across from a guy who could begin a sentence with, “Now, when I was directing When Harry Met Sally…” How could you top that?

I’ve heard others writers say how studios and executives get very excited about a project and then writers can never hear from them again.

The cliché in the business is you have to get used to hearing “no.” That’s not accurate. What really happens is you hear yes and then you never hear from them again.

I feel like that would feel worse than hearing a straight “no.”

In many ways hearing no is a favor. It’s when somebody says “I’m excited about this. I want to do this. Me and you are going to make this happen” then you never hear from them again. It’s like dating. Someone says “sure I’d love to go out with you again” and then they just don’t respond to your second phone call. You can’t take offense at it. That’s the way the business works. You have to get used to people treating you really well for 15 minutes and then never hearing from them again. Be grateful for the people who say no.

How did you first make it to Letterman?

I had a couple of jobs after college and then I finally got a job at the CBS Page program. It seemed like the entry point to get to Dave. About nine months later there as an opening for a full time position. To this day I remember what I said during the interview. The interviewer asked me, “Why should I hire you? Why are you better than the other people?” And I said, “I’m not. I am in no way better than any of the other people. But I will say one thing: You may not give me the job now, but eventually you will because I am never, ever going away.” And I meant it with all my heart that I was never leaving. I wanted to work at this place for so long and now I was sitting in this office building. And how I made it to writer, I’d love to tell you it was just on sheer talent, but it’s honestly not true. It was probably 70% luck and 30% talent. I was friendly with the head writers at the time after working there for four and half years and they gave me a shot. It wasn’t like I handed in a submission and somebody read it and said, “This is brilliant.” But I realize now that, largely that’s how a lot of the business is run.

It’s frustrating because successful people tend not to mention the luck aspect.

It’s so important because it forces you to maintain this degree of humility because you didn’t get there just based on talent. There is a 100% chance there are a ton of people out there more talented than you. That used to motivate me to work harder. I have this philosophy. I think is true. If you’re fairly intelligent, fairly talented, and a decent person to work with, I think everybody gets a lucky break or two. The trick is when you do get that break, have you positioned yourself to capitalize on it? I know people that haven’t where a job opening came about but they had done something to piss off the wrong person. It’s not just about talent. I always quote this passage from Tina Fey’s book Bossypants. She talks about her 3 a.m. test. When she hires a writer it’s not based on just how talented he or she is, it’s about who do I want to bump into at the photocopier at 3 a.m. It’s not an eight-hour day. You need to be able to be stuck in a room with someone for a long time and not want to kill them.

I never felt I was that good of a writer. But I felt like I had more control over my work ethic and I how related to my fellow employees. Joe Torre said if you’re in a slump concentrate on the other things that are slum proof, meaning being a good baserunner or a good fielder. If you’re in a slump at the plate, there are other things you can focus on that are more in your control. I felt how I reacted when I was handed an assignment or when I was asked to work late or I had to do a personal favor was entirely in my control. I didn’t feel like I was a good writer. I’m not just saying that. I really didn’t. I thought at the very least I could pass that 3 a.m test. Like, I’m not going to creep anybody out at the photocopier. At least I hope I wouldn’t.

That would be my advice to people who want to be writers: Don’t neglect those things that have nothing to do with writing. They will play a big part in your future. You have control over that.

Usually when people try very hard to be funny, it doesn’t go so well. How do you reconcile working every day at a job that requires you to be funny?

You’re at a party and somebody asks what you do. And you say “I’m a comedy writer.” I usually get the same reaction, which is: “Oh, I’m really funny. I could be a comedy writer too.” My feeling is always: “I bet you are funny. But it’s Saturday night, you have a drink in your hand, you’re with your friends, you’re in a good mood. It’s easy to be funny.” The challenge of being a comedy writer is doing it when every instinct in your body is not to be funny. It’s Monday morning, you got the flu, a girl just broke up with you, and you have to go to a wedding over the weekend and you don’t have a date because your girlfriend just dumped you. Now be funny. That’s the difference between being funny and being a comedy writer.

When you’re a comedy writer you have to draw upon a completely different muscle and skill set because sometimes you don’t feel like being funny, but you have to fill an entire page with jokes in twenty minutes. It’s different when you’re watching football with your friends and everyone’s drunk and you say something funny and it brings the house down. To be able to do that on command is a far different thing.

How do you sit down and just write comedy on command?

I’m not the kind of person who can sit at a keyboard for 10 hours a day and just write. I can’t sit down to write something unless I know what I’m going to say. I’ll take a walk or just try to figure out what I want to say. I do my writing away from the keyboard. When I go to my computer, I’m not writing. I’m typing what I already came up with. I’m so impressed with men and women who can just sit behind a laptop and bang away for 10, 12 hours a day. I can’t do that. I remember hearing Seinfeld once say that when he started standup he only wrote when he felt like writing. But one day he saw construction workers finishing their lunch and going back to their worksite. He said, “Those guys don’t want to go back to work, but they have to work. That’s the way I need to approach my writing. I need to go to work when I don’t want to.”

Does it help when you’re writing in a group?

I like working with a group for the big ideas. When it comes down to trying to craft a sentence or hit upon the exact wording of a joke, I can’t stand doing that with other people. It’s like doing a crossword puzzle with someone else. Once I’m done with a joke I want another person to take a look at it, but crafting something is very hard to do with more than one person.

But I do love the group dynamic. If you have nothing but a blank page and we need to come up with a funny take on Obama’s campaign event with Hillary, I’d like to do that as a group. I may say something and I may have 60% of a joke, but the men and women in the room are probably going to pitch something that I never would have thought of. That’s the point of having a room. At Letterman we had a brilliant writer named Steve Young who would say something that would be so fucking bizarre and so delightfully odd that I thought: “This is why you do this as a group.”

Have you ever felt a fear or pressure in the writer’s room to think of jokes on the spot?  

That sense of unease when you open your mouth to pitch something never goes away. It’s like in baseball, one of the best hitters in the league once said: “You never lose your fear of the fastball. Ever.” As a comedy writer, that fastball is the dead silence you’re greeted with when a joke falls flat. I don’t think you ever lose the fear of that, but I think you become more okay with it. When I first started at Letterman it was petrifying, especially because the people who I was in the room with I revered. I think now I’m not as fearful because if a joke dies I’ll come up with another one. I’m a big proponent of trusting the room. If no one laughs, move on. The insecurity doesn’t go away, but you don’t care as much. It happened today. I pitched three jokes and they just landed on the floor. But I know it’s not personal. It’s scary the first time you open your mouth, but you just have to get over it. Not to sound like Tony Robbins, but you only have to do something for the first time once.

Is it difficult to make a living working on TV shows?

Well around the time we were pitching is when me and Jeremy applied to work for Wilmore. We put the projects on the back burner, but we’d like to revisit them because ultimately that’s what we want to do. We kept busy, but there was still a fair amount of downtime which took a lot of getting used to. But you sort of just hustle, try to find jobs here and there. That’s the life of a writer. Whenever I talk to young writers or interns who ask for advice I always say my job at Letterman is not how TV usually works. You don’t normally have a job that lasts for 20 years. You get a job and it lasts for a few weeks or a few days and it hopefully leads to something else. And you hope one day instead of constantly calling people asking for work, somebody calls you.

What’s your experience in seeing the work ethic of late night hosts?

It’s tough to host a show. My friend worked for a talk show about 10, 15 years ago. It only lasted for a couple of months. The person who was hosting the show had already made his name in another field. He was always a good guest so when he got a show he thought, “Well I’m going to be a great host because I was a great guest.” A lot of the people who worked for him came from the late night world. They would always tell him: “You don’t’ understand. Letterman’s the first one in the office and the last one to leave. Nobody works harder than him. This didn’t just happen.” And Dave might be the most gifted broadcaster of his generation. I think he is.

People always said Michael Jordan is not only the best basketball player, he’s also the guy who works the hardest. So my friend came away from that experience and he said: “Never work for someone who doesn’t need the money.” I think that’s a great lesson. These men and women we’re talking about, they want to host these shows. I was talking with somebody who worked on Late Night with Jimmy Fallon and they said: “You have no idea how hard he works.”  People don’t realize these hosts don’t just walk into the studio fifteen minutes before showtime, slap on some face paint, and begin the show. When you see their faces in front of that camera they’ve been in at that building 12 hours before. You can usually tell by the quality of the show.

From Letterman to Wilmore: Inside Network and Cable […]