Welcome to the very first edition of “Writers’ Room,” a soon-to-be recurring LateNighter feature where brave comedy writers dare to tell us all about the business of writing jokes.
If at first you don’t succeed, try, try again—until Seth Meyers finally reads one of your jokes on air.
Writer and comedian Mike Drucker has been around the late-night television block. He penned jokes for Jimmy Fallon for about five-and-a-half years—beginning on Late Night in 2013 then moving to The Tonight Show, where he remained through the spring of 2016; he then returned to The Tonight Show in October 2022 and stayed through January 2024.
Drucker was also a writer on Full Frontal With Samantha Bee from January 2018 until the show’s cancellation in July 2022. Additionally, he has written for Mystery Science Theater 3000, Bill Nye Saves the World, The President Show, Science and Star Wars, and Adam Ruins Everything.
However, writing jokes didn’t always come so naturally to Drucker. In fact, he insists that he used to be pretty terrible at it. As an eager young intern at Saturday Night Live, he would submit joke after joke to “Weekend Update,” only to watch none of them land. “I got nothing on [air] for years because I was very bad at it,” he tells LateNighter.
Still, Drucker kept at it. Today, he has eight Emmy nominations to his name, including Outstanding Writing for a Variety Series for both The Tonight Show and Full Frontal. Clearly, he knows a thing or two about telling jokes (and his loyal X/Twitter following is all the more proof).
Below, LateNighter chats with Drucker about his comedy career, the fun challenge of writing jokes in Jimmy Fallon’s voice, the “stupid” joke about Leonardo DiCaprio he can’t believe actually made it on air, and more.
How did you land The Tonight Show gig?
I had been doing standup in New York, and through luck and knowing somebody, I knew there was an internship available at NBC in the casting department. I was like, ‘I want to work in television,’ and they were like, ‘Oh, we’ll hook you up with something in comedy.’ They hooked me up with an internship at Saturday Night Live. I was standing up, I was taking improv classes, I was doing this internship, I was at NYU. I was kind of throwing everything at the wall.
I finished the internship, I moved on, I did other jobs. I came back to Saturday Night Live as a photo researcher, and I started to get jokes on “Weekend Update.” [But] I kind of realized I wasn’t going to be a writer there for a while. I decided to take a job opening at Nintendo of America in Seattle, and I did localization work for video games for a couple of years. While this was happening, comedy was starting to take off. I did the [Just For Laughs] Montreal comedy festival and got noticed by a couple of places. There was a job opening at Late Night with Jimmy Fallon, and I got hired there as a staff writer.
Do you remember the first joke you got on the air?
I think it might have been like, “The inventor of the trampoline died this week. His family will always remember his last words: ‘Look what I can do.” It was Seth [Meyers] who said it, I think. That was a very cool moment, because I was like, “OK, at least I’m doing this once, even if it never happens again.” It’s like when you read about a Zamboni driver who gets to be a goaltender for eight minutes. You’re like, “Oh, that’s nice you got to do that.”
When you worked on The Tonight Show, how many jokes did you typically write a day?
It would depend on the day, but I personally would write a lot. My writing style, especially when I was in the monologue department, was that I would overwrite, then cut down, and then submit. On an average day, maybe 100 or 200 [jokes]. On a day where we didn’t need a lot, maybe a couple dozen.
What was it like to write jokes in Fallon’s voice?
The fun thing about Jimmy is that he comes from impressions, so if you want to do something that’s sillier, or a little over-the-top, or a song, he’s much more game for something like that. When you write for any host, you almost are doing an impression of them in your head. When I’m writing for Jimmy, I’m writing for someone who’s a little more playful and likes being a little more silly, versus someone who’s looking straight into the camera to solve America’s problems.
Is there a certain kind of joke that Fallon hates?
Jimmy’s aware of families watching the show, so he likes more family-friendly [jokes]. We tend to avoid things involving sex or being mean for the sake of being mean. He was always open about it, so it wasn’t like we were confused—I was always aware that it was more of a family audience watching the show.
What was the biggest difference between writing for Fallon versus writing for Samantha Bee?
Well, they’re just very different shows. Writing for Sam Bee was writing for somebody who was doing a political show that required an entire team to research specific topics. When you’re writing political jokes for The Tonight Show, it’s not necessarily as big a part of the fabric. So, it was just that they were very, very different shows—which is why the Academy of Television Arts & Sciences is constantly like, “How do we parse what awards to give which of these?”
What’s a joke that you were surprised got on air?
There was some news story about how Leonardo DiCaprio had sued a magazine in France for some rumor that he had gotten somebody pregnant. The award was $9,000—that’s a lot of money to normal people, but nothing to Leonardo DiCaprio. So, I pitched this long bit where Leonardo DiCaprio talked about what he was going to do with $9,000 and how he was going to, like, buy a couch and invite girls over to watch his big screen TV. I felt like there were no legs and it was just too stupid, but it actually went on air, and I was very happy about it.
What’s the biggest misconception about working as a late-night writer?
The biggest misconception is that every late-night room is the same. Every room is extremely different. I don’t mean in terms of who’s in it—although depending on the show, that can or cannot be true—but also, how a show comes together. The way that those rooms operate, the way that people pick jokes, the way that sketches are processed and made… every host has a different way. I think sometimes there’s this view that it’s monolithic, but every show that I’ve worked on has been so different.
You spent several years working with Samantha Bee. What’s your best guess as to the historic lack of women hosting late-night shows?
I mean, there’s a ton of factors involved in that. One, it sucks—I enjoyed working for Sam a lot, and I certainly wish they still had her show [on air]. I think that a lot of networks sort of resort to what is “comfortable.” What’s frustrating isn’t the fact that we have the hosts that we have now, what’s frustrating is that women keep getting taken off the air. The problem isn’t that John Oliver has [a show], the problem is that Amber Ruffin doesn’t get necessarily as much support as she could, or that Sam doesn’t get as much support.
Finally, who was your favorite late-night guest during your time on The Tonight Show?
Weird Al. I asked permission to meet him—the show was nice about you possibly meeting people, but you have to be polite, because everyone’s there for a job. Usually when people asked [to meet guests] it was because their kid wanted a baseball signed or something. But I was like, “Can I meet Weird Al?!” He was the nicest dude. My mind was so blown.
The interview above has been edited for length and clarity.
