interview: Raf Esparza, NBC Late Night Writers Workshop

I met Raf back when I was a fellow in the Nick program. He had taken a meeting with Karen Kirkland, and she introduced us. When I heard that NBC was starting a Late Night Writers Workshop, I thought Raf would be great for the program, and it was no surprise to me when he got in.

Congrats on having been chosen for the inaugural Late Night Writers Workshop! You seemed like the perfect candidate because you’ve been doing this for a while: you worked on the Tonight Show as a coordinator, submitted jokes, and you perform a late night talk show at Flappers Comedy Club. How did all that help you write the material you submitted?

Hey Kiyong, thank you so much for the nice words (please do not cash the check I gave you to say said nice things, it won’t clear until the end of the month).

For me, the Late Night Writers Workshop was the cumulation of all the little things I’ve tried to do for the past five years—including my time at The Tonight Show and the creation of my own late night talk show Early Late Night.

At The Tonight Show I learned the discipline needed for a successful writing schedule and the ability to persevere through constant rejection.

Writing monologue jokes is a pretty thankless job (even when you do get paid). You spend hours of your time researching, sifting through news articles trying to find the best takes on the day’s headlines. The minute my shift would end, I’d sit at my computer and force myself to write for at least another hour. After a full day of work, I’d be tired as hell—but sticking to that routine was something that I knew would one day pay off.

I didn’t get a ton of jokes on at the very beginning and would often get discouraged—until one day one of the most prolific writers at the show (an awesome writer named Jon Macks) shared the following statistic: for every 100 jokes you write, 1 will get on air.

Now just take a moment to really think about that number. 1. For Every 100.

That’s a 99% rate of failure—which, for most professions, would be enough to prompt a rationale human being to say “thanks, but no thanks.”I can’t imagine a great deal of patients would be cool if their doctors told them mid check-up, “by the way, I do this successfully 1% of the time. Now, about that cancer…”

It also may explain why so many comics are crazy.

But, for whatever reason, be it stupidity or thrill of the chase, I heard that ratio and thought, wellits not impossible. With that in mind, I just kept plugging at it, knowing the result wouldn’t necessarily mean a joke on the air every night, but I was convinced that the routine would cultivate a stronger writing voice.

Eventually that routine turned into jokes getting on air, which turned into Flappers entertaining (and then actively pursuing) my pitch for a full scale talk show (and a two year residency of writing and produce my own full scale talk show on a monthly basis).

I sometimes refer to Early Late Night as an aptitude test—a chance to demonstrate all of all the things I’ve learned in Late Night (be it production, booking or helping new talent learn the late night format). And because the turnaround time can be very fast (and I mean fast!), a strong foundation and work ethic can help you determine very quickly what bits will or won’t work and where jokes need to be punched up.

So when it came time to put together a packet for NBC, I had one main goal: to submit a packet that was the best representation of me as a writer. While I was initially scared of submitting a subpar packet, eventually all of the little things I had been doing for the past few years started to come together. By the time I submitted it, I honestly felt that even if I didn’t get in, it was a great representation of who I was on that very day.

When they called to offer me a spot in the Late Night Writers Workshop I genuinely felt a great sense of validation. I was always proud of the work I did at The Tonight Show and Early Late Night, but the spot in the program really was a special moment that justified all those late nights staying in the office to write jokes.


Let’s cover the basics of the program. How long was it? How many people were accepted? What did you work on in the program?

All together they accepted eleven individuals—including myself and one writing team. Initially, the workshop was only supposed to be a two day program, but they ended up getting us into a Fallon monologue run-through the day before everything started, so it thankfully ended up becoming a three day thing. The extra day gave all of the participants some time to get to know one another before the intensive workshop and to complete the homework.

Did I mention we had homework?

They gave each one of us a copy of the other workshop members’packets. So you had to go through all of their monologue jokes and sketches and write some notes—which is great for me, because I thrive off of notes. I also loved that as you read each packet you really got a sense for the other writers’personalities. During my time with the group, I found that the people they selected didn’t just happen to be great writers, every. single. person. had a great story and passion. And it really brought the class to life.

We were also told to bring two creative late night specific assignments to the class.

I spent my time revising the assignments over and over again, just to try and get it right. But the beauty was in the imperfection. Once you got to the workshop, you spent hours of time reviewing choices, options, ways to interpret and take the joke. Our instructor, the incomparable Jonathan Reynolds, was instrumental in teaching us the fundamentals of game theory and set guidelines on how to strengthen our monologue jokes.

Even though so many people in the room had experience working at a late night show (many of them interned at Conan or The Colbert Report), these exercises were designed to get you to dig even deeper—and I think it was a challenge that was embraced by all. Personally, I loved being a part of a group of late night nerds who all exhibited the same passion for late night that I did.



They flew you out to New York, and you got to meet Jimmy Fallon and Seth Meyers, which is pretty awesome. What did they say? What did you learn? 

For the program, we got invited to a Fallon monologue run-through—which is really unique in terms of show production, as neither Jay Leno or Conan O’Brien really do monologue run throughs. Jay tests out his material on the road and Conan O’Brien just thumbs through jokes at his desk on stage and mercifully mocks his staff (to their delight) in what can be described as a “very loose”rehearsal. Jimmy, on the other hand, actually brings in a small audience to do a full run through of monologue jokes and desk bits to figure out what works and what doesn’t. So it was us and a bunch of random tourists who—despite being very excited—were no match for how pumped we were.

When we arrived, it was almost like an attraction at a theme park. Outside of the studio, you get a short warm up and history of the show, then you walk into the studio, Jimmy promptly greets you, and then BAM: rehearsal. Jimmy gave us a nice, subtle acknowledgement up top, but we were all there to watch him at work.

It was fun to watch how the tourists watched the rehearsal vs. the way the workshop members watch the rehearsal. We all quickly spotted the Fallon writers and watched them furiously scribble notes as Jimmy delivered each punchline. And because the team was taping two episodes that evening, they had a great deal of material to thumb through. Hell, even I was even jotting down notes in my notepad and ranking the jokes.

For all of us, the gift of this run through was learning how to react, read the room, and make arguments as to what bits were strongest—because right as we exited the room, that’s exactly what took place with Fallon and his staff.

Our meeting with Seth was completely different. We got word that we might have a surprise guest join us for the first day of the program. During dinner, one of our program heads, the delightful Julie Ann Crommett, broke the news “someone special”might be joining us for day one. I didn’t need any other convincing, I knew right then and there Seth was going to make an appearance and talk with us.

In the morning, my suspicion was confirmed by our program head, Karen Horne, who told us we’d get a visit from the soon-to-be host of Late Night. In walks Seth who greets each one of us individually, conversing with us and taking genuine interest in our comedy backgrounds. With him is his producer, Michael Shoemaker—who, unbeknownst to him at that time, is a personal hero of mine.

So Seth sits and talks with all of us for over and hour and a half. The first thirty minutes or so, providing practical hints at what he does/does not prefer to see in a late night packet (having read through a number of them during his time as Saturday Night Live head writer). And I think that’s why so many of us thrived on Seth’s every word. Not only is he a performer, but his roots were deeply entrenched in the same struggle that we all face every day: how do we create the funny in the writers room?

It was a fantastic contrast. With Jimmy we got the chance to watch a show being created right in front of our eyes and with Seth we had a host giving us tips on how thrive in the writers room—two completely different skill sets that are instrumental to the process of producing a daily show. And those were just two of our speakers, our program heads did a phenomenal job attracting other speakers who joined us during the workshop.


Do you think being able to write funny jokes is good enough? Or do you have to be able to perform?

I’ll say this. You don’t need to be a performer, BUT it certainly doesn’t hurt. During the workshop, there were a number of scripts that we cold read at the table (that tend to show off those best with some degree of sketch, improv or character-based creativity). And while you wouldn’t get thrown out of the program for a bad table read, a fellow writer is always happy when you make an earnest effort to commit and sell their material.

Fortunately, I had a number of impressions in my bag that suddenly became useful during our table reads (while I expected to dust off my Jimmy Fallon impression, I had no idea I’d be utilizing my Tom Petty and David Bowie)—and that kind of confidence can only come from being on stage and exercising those performance muscles in front of a live audience on a regular basis.

Having said all that, if you tend to be a bit more of a shy, reserved individual, you can still find a place on these shows as a writer. The writers I’ve interacted with over the years have been all over the personality spectrum. Some are content just sitting in their offices writing mono jokes, others have extensive experience in improv and stand-up.

The important thing is to be keenly aware of your strengths and utilize them to your advantage. For me, the ability to create characters and do impressions is a strength. So when I walk into a room, I know I have that in my back pocket. I don’t walk into a room screaming, “everyone ask me about my Sean Connery!!!.”But if asked, I can recite some lines and get some laughs just for being prepared.

I also like to think I have a good ear for joke language and syntax. If the joke in the room doesn’t sound quite right, I’m quick to offer words/slants (or altsalternate takes) that sound more like the host. It’s a wonderful, quiet confidence that makes all the difference.

At the workshop, a great number of the folks came in with some kind of performance background. And while not everyone identified themselves as a perfumer, each of them knew the thad a fundamental strength or two they were comfortable contributing to the room. So whether you’re an introvert, extrovert, or some kind of hybrid alien of the two, find out what that thing is you can contribute to the room and own it.


You worked on The Tonight Show when during Conan’s brief stint, and then when Jay came back. How different was the show during that time with those different hosts?

Let me say this up front, I think both of these guys are immensely talented. I don’t like it when people say they hate a certain host. There’s too much in this world to actually get worked up about, rather than hating someone who’s humor doesn’t quite connect with yours. Comedy’s subjective and I think Jay and Conan are successful because they not only understand the mechanics of what is funny to them, but also what speaks to their audiences.

Conan’s approach is so impressive. During rehearsal, he recites each joke like a managing editor at a newspaper with a red pen. When he sees something he doesn’t like, he nixes it. When he notices a joke isn’t quite there yet, he’s dynamically fast with a punch up or fix. I’ve often said they need to record the show that happens during rehearsal because that Conan is untouchable. It’s the kind of ethos that can only come from being a head writer. He’s loose, he’s comfortable, and the interaction with his staff is just priceless.

I think we all agree, we never got that chance to see him get his fair shake. I remember reading an article from the Los Angeles Times right before he was going to take over The Tonight Show where he said, “don’t ask me what works after the premiere, ask me what’s working in six months. That’s about the time when I think I’ll start to figure out what works or not.”Anytime I read something about how Conan didn’t know how to find his right 11:30 pm voice, I think back to that article. Jay faced those same struggles during his first few years as the host and ultimately found a vibe that worked for him through a trial and error process that was afforded to him.

In 2009, I thought both Jay and Conan struggled creatively to do their shows with so much pressure. NBC’s entire primetime line up was a disaster and suddenly Late Night had to be the one to both save 10pm and maintain it’s dominance at 11:30pm. In that period, I think you saw both The Jay Leno Show and The Tonight Show with Conan OBrien working overtime to please not only audiences, but, more often, their employers.

And while that was terrible time professionally for those two hosts, I found myself thriving as a page in the NBC Late Night Programming offices—doing coverage of all NBC’s Late Night programs (including SNL’s on both Thursday and Saturday, Last Call, and Late Night with Jimmy Fallon) and offering some constructive feedback any time someone remotely asked. And, to my surprise, I found that sometimes, my input was actually valued and utilized.

In the end, I think both hosts ended up just fine.

Conan became a cult hero who went out in a blaze of glory with a set of shows at The Tonight Show that rank amongst the best late night television I’ve ever seen—AND got the chance to pull a Letterman, cementing (perhaps) an ever bigger legacy by creating a franchise talk show at another network. It also gave him a fantastic digital fanbase that may ultimately serve him well in the long run, as many wonder how big of a role digital viewing plays a process in ingesting late night programming.

Meanwhile, Jay got the chance to prove he could make his way back to the top (despite a tidal wave of negative press), restore a sense of calm among the NBC affiliates and executives, and successfully execute a transition of the show at #1 to another young comic host with a lot of talent. When people attack Jay for being this machiavellian character, I’m not sure they ever really knew how good he was to his staff. That one gesture to work with NBC again saved all of his staff’s jobs, including my own. And if you’re looking for work ethic, you’d never needed to look further than Jay’s parking spot. He arrived before most of the staff and would often stay later than most of us.

Ultimately, I think Jay got the fitting Tonight Show end he truly deserved this time around. That last episode of his show was something special and a much more fitting end to his tenure as host.

But both made millions. Both have undeniable contributions to the Late Night genre. Both have an amazing reverence and respect for the institution of The Tonight Show. For me, it was an honor to work for what I consider to be the best franchise of all of television—and for both of those hosts.


You got to pitch jokes to the Tonight Show when Jay was hosting. How did you get that opportunity?

By accident, actually. I’m a big proponent of doing informationals (or general meetings with “important people”). I’m a people person and one of the best ways to put yourself out there is to go out and network with as many folks as you can. After my first year on the job, I made a point to introduce myself to more people on the staff as possible. Around this time, a great friend and colleague at the company, Christy Florio helped me think outside of the box to arrange a meeting with a former NBC bigwig. We were able to track down him down and he graciously gave me an hour of his time. Without wasting any time at the top of the meeting, he looked at me and said, “What do you want to do?”

I gave him my safe, stock answer of “well, whatever’s good for the show, I can pretty much do whatever job is put in front of me.”

My answer didn’t seem to phase or impress him, he pressed on, “No. What. do. you. want. to. do?”

“—I want to be a writer.”

I paused for a second after saying it. I had always been told not to by weary about mentioning an interest in being a writer to important people. “This town has plenty of assistants who daydream about being writers,”they said. “Don’t be that cliche. Bring it up when the time is right.”

Then, right then and there during lunch, he got out his phone and made some phone calls to the very people he hired at The Tonight Show on my behalf (including our executive producer). And suddenly I’m in a series of meetings with people who all started their meetings with the exact same question. “What do you want to do?”

I tell each one of them point blank: I want to be a writer. Pretty soon I found myself in a meeting with our monologue coordinator who asks me to write some topical jokes for a few days. The general premise being: if they like my work, they’ll ask me for more. Lucky for me, they did.

The biggest takeaway I discovered during that process was to just be honest with people right up front. Now any time I meet with someone for the first time and they ask me “what I want to do”, I tell them I’m a writer.


Any advice for aspiring comedy writers?

In keeping with theme of Late Night (and as a tribute to the recent announcement of David Letterman’s retirement), I decided to give you a Top 10 list.

10. If you want to write for late night, watch it. Every night. No excuses. I DVR every late night show or catch the monologue on Hulu. It’s a pain in the ass, but it’ll keep you up on the trends and steps ahead of everyone else.

9. The only way to start writing for late night is to start writing. Learning how to craft the perfect monologue joke is a muscle that you have to continuously practice. Twitter and Facebook can be a great place to start (to get feedback), but concentrate on the routine.

8. Make sure the joke is no more than three lines in length. If the joke needs any more set up or execution, it’s no longer a monologue joke.

7. Once youve pared a joke down to three lines, take a good look at it and keep whittling(e) it down until you can get it to two. Brevity is key. Edit constantly to take out all the unnecessary words.

6. Find a writing group. Seriously. Writing groups will hold you accountable and they’ll often be relieved to take a break from reading nonsensical Scandal specs to read jokes.

5. Network like crazy. If you aren’t networking, you’re likely missing out on that next great gig. Find the people who like the same things you do and make friends. But don’t be a d-bag about it, be honest and make connections with people that are meaningful.

4.   Always take the meeting. If someone new to the world of entertainment wants to meet with you, take the meeting. You never know who you might meet. (BONUS TIP: If you can lend a hand to someone who needs your help, do it. Don’t bother thinking what you’ll get out of it, just try to help people, always.)

3. Surround yourself with positive people. This is a tough business and you’re going to be around hundreds of people who tell you that you cant. Figure out who those positive voices are in your corner and treat them amazingly—they’re gonna be the support network you need the most when things get rough.

2. Never be afraid to try something new and different. There are hundreds of writers out there, but personality in your writing makes a huge difference. Never be afraid to be you.

1. If you love it, never stop writing. The constant rejection and haters will try to drag you down, but always hold on to that thing that made you want to become a writer each time you get behind the computer. And if you can do that night after night, you’ll never want to stop.

And, above all, have fun. Always.

– – –

A big thanks to Raf for sharing so much of his experience! I hope you’re as motivated by his work ethic as I am. You can follow Raf here:

twitter @EarlyLateNight
Facebook: EarlyLateNight
Instagram: EarlyLateNight
YouTube: Rafesparza

and some clips:
2013 Highlight Reel
2012 Highlight Reel

Similar Posts

One Comment

Leave a Reply