A multi-talented director, producer, writer and comedic actor known for his roles in Wet Hot American Summer, Wainy Days and the short-lived Dog Bites Man, A.D. Miles made the challenging transition to late night in 2009 as the Head Writer of Late Night With Jimmy Fallon. In his first experience with late night, and the singular challenge of generating nearly 1000 hours of television over the course of five years, Miles wasn’t alone. Late Night marked Fallon’s gig as late night host, and was staffed with a group of first-timers who could bring a fresh perspective to late night—a strategy that was similarly adopted as Fallon and Miles transitioned to the historic Tonight Show in 2014.

Thankfully, since the time of that transition, there has been no shortage of fodder for comedy and conversation, as one of the most bizarre, frightening and absurdly funny presidential races in history continues to unspool. And as that race moves toward its dramatic conclusion, Miles wakes everyday to new comedic offerings and renewed inspiration. If only Miles and staff can get to the punch before everyone else. Below, Miles discusses the odd intersection of politics and entertainment in 2016, the process of securing presidential candidates as guests, and the reasons why Donald Trump is the best thing that ever happened to late night television.

With your transition from Late Night to The Tonight Show Starring Jimmy Fallon in 2014, were there growing pains in finding your place within this historic franchise?

I don’t know if I would categorize them as growing pains. These shows are unique in the sense that you do them every single night, and there’s obviously going to be ebbs and flows when you’re creating so much television. So the biggest pain is trying to maintain a high standard over so many hours of television.

I think the way that it’s evolved is that we’re always learning, and the landscape of late night television just keeps changing so much, but we’ve gotten better at adapting. When we started out in late night, everyone was new to the format. Jimmy was new as a host, I had never worked in late night before, and that was all by design; they intentionally picked writers who were coming from other places. We were basically just figuring out how to do it and make it our own.

That took up a lot of creative energy and brainpower for the first few years. Then, when we kind of got our voice, it’s just been about trying to maintain a level of output. We were so ambitious at the beginning, with the very long, elaborate pre-tapes, and parodies, and things like that. It’s weird when I look back on it. I thought, we’ll never be able to keep this up. Then, in a suicidal way, you kind of just get used it.

We also came into late night in such a unique time—normally, the changes in the late night landscape are very tectonic and sort of happen very gradually, and very rarely. Then, when we came along, it seems like every couple of years there’s this seismic shift about either new shows, or new hosts. It’s just been crazy, but in a good way.

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In addition to his writing duties, Miles (pictured left) finds time to perform frequently on the show. Here, Miles sings an a cappella version of Jason Derulo’s “Talk Dirty” with actor Kevin Spacey and The Ragtime Gals.
Nathaniel Chadwick/NBC

To what do you attribute your ability as a staff to generate such an overwhelming amount of content on a consistent basis?

It’s tough, but there’s no real magic to it. It’s just generating lots of options, which is probably one of the more painful parts about working in late night, in that we just have to create so much stuff that will just never see the light of day, for various reasons. We have learned to not be too precious about stuff.

Also, we’re fortunate, in that Jimmy has ideas of his own that are definitely nothing that you would ever pitch, because they sound insane. But when he thinks of it, we’ll kind of be like, “Oh, sure, yeah, two James Taylors on a seesaw. Okay. We’ll get to work on that.” And then the next thing you know, the call goes out to James Taylor, and it’s actually happening. And you’re just like, no one would have ever had the balls to pitch that idea.

Some of the crazier, more unique moments to the show are just things where Jimmy says, “What about this?” Or, “I had this dream.” We did something weird where we had Lionel Richie on the show and we recreated the “Hello” video; Jimmy was a potter, and Lionel Richie’s head was in the middle, and it actually came to life. Jimmy was like, “I dreamt about this the other night.” We were like, okay, let’s make a bit out of it.

Do you have the bandwidth and time, on top of your writing duties, to keep track of what’s going on elsewhere in the late night landscape?

I guess I make the analogy of a professional baseball player, who goes home, and I don’t think that the first thing on his mind is to go out to a baseball game.

We’re certainly aware when moments on other shows become viral, just the way that anybody who consumes a lot of media are aware of things that come up through the ether. But there wouldn’t be the time in the day to sit and watch the other shows, other than their best moments. If I can struggle to watch The Bachelorette with my wife before I pass out, that’s usually about the best I can do.

Your submission for the Emmys’ writing category, episode 307, marks presumptive Democratic nominee Hillary Clinton’s first appearance on the show. How do you, as a writing staff, choose to handle politics on The Tonight Show?

There are plenty of shows where you can get the breakdown of a political point or a more thesis-based comedy, where you take an issue or a politician and hold their feet to the fire. There are people at it, Samantha Bee and John Oliver and people from the school of Jon Stewart who are so amazing at it, but they are speaking to their audience.

What our show does is more in the broadcast vein. We’re not apolitical, in the sense that we do talk about the election, and we make jokes at pretty much both sides’ expense, because our audience is from coast to coast and everywhere in between.

I don’t think anybody looks to us to teach them about politics. What’s good about the way that Jimmy has handled it in interviews and sketches is that it is usually very silly. We’ve had Donald Trump on, talking to Jimmy as Trump in a mirror. We’ve had Bernie Sanders on and played a game with him. We usually give people a few minutes to get their talking points out, but then it’s like, okay, now you’re going to be in a sketch. I have to say, most of them have been pretty game and pretty loose.

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“We’re fortunate, in that Jimmy has ideas of his own that are definitely nothing that you would ever pitch, because they sound insane,” Miles says.
Douglas Gorenstein/NBC

The history of presidential candidates and high-profile politicians going on late night dates back to JFK, but it seems that there is something unique going on in late night at this point in history.

Certainly with the Republican frontrunner being a former television personality, the line between politics and entertainment gets thinner and thinner.

And I think that also with social media, it’s kind of bled into broadcast. They realize that they kind of have to play ball, and maybe even it was The Daily Show that turned politics into entertainment; they’ve kind of become one and the same. This election is such a reality show on its own. I don’t know that there’s that much of a distinction anymore.

I think when you’re talking about the older days—JFK or somebody coming on—there was a reverence. The President is here. We can’t really be coarse, and we have to watch our language around these guys. Whereas now, it’s like, hey, you’re going to come on and you’re going to do a straight-up comedy sketch. Trump and Clinton and Bernie, I believe, have all been on Saturday Night Live. I mean—that’s crazy, you know? To think that somebody who might be the leader of the free world is coming on all these late night comedy shows and doing bits. It’s great.

It’s an amazing boon for us. I don’t know how good it is, necessarily, for the country.

What can you say about the process of bringing these political figures onto the show, and incorporating them into sketches?

The only difference in one of these guys [versus] a celebrity is there’s a bit more vetting that goes on with the bits. The lead-time for getting the materials and what we’re planning on doing is a little greater. So far, I don’t think we’ve had a single person not do the bit that we pitched them.

I guess that comes from the reputation of our show, where we’re not going to sucker punch you; we’re not out to make you look bad or good, necessarily. We’re just here—like, come play. Mainly, we’re here to entertain our audience, and if you want to be a part of it, great. They’ve all seen our monologue, they’ve seen the jokes we tell about them, and are still willing to come on and play ball.

In Clinton’s episode, Fallon refers to Trump as “the best thing that ever happened to our show”. Is there some truth to that statement?

 Oh, yeah. Definitely. He’s the best thing to ever happen to late night, not just our show.

It’s sort of analogous to that moment when the Anthony Weiner scandal came out—I remember Jon Stewart had a moment when he was like, okay, hold on a second… his name is Weiner, and he sent a picture of his wiener.

So when Donald Trump comes along, I feel like there’s a moment where you can’t quite believe that this guy is for real, and you can barely keep up with the news cycle of the things he’s providing you with. Because the other politicians have to react to that, it creates their own moments where you can jump in.

You always hope for some political foible or something like that that’s going to allow you to make jokes, and the election season is, of course, always a very ripe time for that. But this particular election season, it’s an embarrassment of riches.

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“[Trump]’s the best thing to ever happen to late night, not just our show,” Miles says.
Douglas Gorenstein/NBC
 Looking back, what was it like to have both Clinton and Trump on the show as headlining guests within the span of a week?

It makes you feel lucky. It makes you also feel like you have a responsibility, because you realize that with the frontrunners both being on your show within a short span, you are going to be attracting a lot of eyeballs. I think there is some pressure there to make sure that you get it right, as far as execution of the sketch and making sure that it’s absolutely as funny as it can be.

It’s both tricky and a benefit of our show that we can have such diametrically opposed people within the same five days and neither one of them seem to have a problem with it; neither one wanted to distance themselves from the timeslot of the other. I think it just shows the wide reach that the show has.

The Tonight Show is regarded widely as the most important franchise in television history. Apart from ratings, how do you evaluate the success of any particular show or season?

Well, A, did we keep our head above water? I don’t know that we sit around and think about the strategy of a yearlong show as far as shaping the voice, because so much of what we do is reactive to what’s happening in the news and in pop culture. We’re usually dependent on what’s happening out in the world to create the material that we’re going to use.

Strategy-wise, it’s a race. You’ve got this super crowded late night landscape where there’s so many shows, and you’ve got Twitter, where people are racing through the low hanging fruit as soon as it can get to their phones whenever something happens. So there’s just this incredible competition to make your voice unique enough for people to want to watch it, and also to get to your best take the fastest. That’s basically what we come in doing every day—what’s the best way for Jimmy to approach this thing that just happened? And how do we do it today before somebody else comes up with a similar idea and takes the wind out of your sails?