Interview: NYC comedian and TV writer Kevin McCaffery performs this weekend at Penguin’s

Kevin McCaffery at Penguin's
“My affiliation with Letterman is certainly my favorite TV job,” McCaffery said. — photo courtesy of Kevin McCaffery

Comedian Kevin McCaffery

Penguin’s Comedy Club — Sept. 5-6 at 7:30 p.m.

Kevin McCaffery, a stand-up comedian and writer based in New York City, will be performing at Penguin’s Comedy Club on Friday Sept. 5 and Saturday Sept. 6. He has written for and been featured on a number of television shows and hosts his own podcast, College Stories, where he invites people from the entertainment industry to discuss the good and not-so good experiences from their college days. Little Village talked to him recently about his experiences writing for television, his stand-up act and his work with Late Show with David Letterman.

Little Village: You did a stand-up set on Letterman last year, but you had actually been a writer for the show at one time. Is that correct?

Kevin McCaffery: I have done freelance work writing for the monologues, but I started there as an intern at the end of college in 2004. I actually ended up writing for the “Top Ten List” under the table during that internship. One thing they made clear in the beginning was that just because it’s called the “writer’s internship” doesn’t mean you are actually interning to write for them. The job is that you’re a writer’s assistant — you call in the lunches and you print off assignments to hand out to everybody. You will not be writing.

But then there was one day on the show where right before Dave headed out on stage, he looked at the Top Ten List that had been given to him and he put a big X through all of it, and he gave it back to the guy as he walked out on stage. So, the writer’s assistant came upstairs and was freaking out because they all had to basically write a new list in five minutes.

To keep my brain from atrophying while covering the phones, I would write on what the topic the Top Ten was for that day. So the assistant looked at me and asked, “What are you writing?” And my first response was to just reassure him I that was being a good intern, like, “nothing …certainly not overstepping my bounds in any way.”  He picked up the sheet I had written on, and it had like six entries. From those, I ended up getting number nine and number one on the Top Ten List. And then they asked me, “Do you want to just keep doing that?” And, of course, I said, “sure!”

The stand-up spot that I did last year though, didn’t come about from writing on the show. That came about separately from doing stand up.

You were featured on both I love the 1880’s on the History Channel and I love the 2000’s on VH1. Are there other periods of history you are fond of?

Yes, I love a wide variety of decades. But, honestly, between those two, I really enjoyed doing the I love the 1880s. It wasn’t just about that decade, but just history in general. I’ve done a bunch of the VH1-style clip shows, and it was fun to get to do that tone of comedy but with talking shit about Andrew Jackson’s giant cheese wheel that he had, for some reason, and all these other weird historical things. That was fun. There is a lot of fucked-up stuff in history — the Salem witch trails — you can talk a lot of shit about the Salem Witch trials. That was crazy.

I enjoyed I love the 2000’s also, but it made me feel very old because it was like, “Hey, remember that thing?” And I felt like, “Yeah, I think that literally just happened.” Though, on the other hand, I guess if I didn’t remember it, I would have some serious memory problems.

You were a commentator on TruTV’s World’s Dumbest Criminals. Did you come across a world’s dumbest criminal?

I would say there was a solid four dozen clips we had of dudes in trucks trying to throw a chain or belt around an ATM and drive away with it, and it just literally never worked. So I would say there is not one dumbest criminal, but, in terms of dumbest crime, I think that is up there just because of how many people fail at it.

The events in Ferguson have brought a lot of media attention to police incompetence across the country. Do you think there could be a World’s Dumbest Cops?

I would totally be on World’s Dumbest Cops. There is no doubt you could find twenty clips for that. It would just be a matter of finding ones that don’t only make you angry and sad. If you could find twenty like “Hey, look at these dumb cops,” but where they didn’t totally ruin someone’s life.

Is the way you approach stand-up comedy similar to the way you write monologue material? Do you try to write out all your material in a lot of detail?  

I don’t really write out my stuff word-for-word. I’ll have a topic and a couple of points and then I go up. I guess you would call it “writing on stage.” Writing a Letterman monologue is wildly different than anything I do with stand up because, obviously, the monologue is really topical, and it is very much about moving from the set-up quickly to the punchline. My stand up is more conversational and about storytelling. It is much more of a long-form style than monologue jokes.

What is the New York City stand-up scene like? What do you find unique about it?

New York is very lucky to have a very good indie scene away from the clubs. There are cool clubs too, but one thing New York has that a lot of other places might not have is a number of really cool independent shows where you can do different stuff or do what you think is cool. There are ton of great little independent shows that are happening all the time, mostly in the East Village and Brooklyn. Those one-off or once-a-week shows in a bar are a lot of my favorites.

There is a place called Kabin’s which is on the Lower East Side that has comedy every Thursday. It is just a super-divey bar. You wouldn’t even know there is a back room unless you walked far back into it. People who go there want to have a good time and want to see comedy. You’ll have comics like myself and younger indie comics on the line-up, but then you’ll also get Jim Gaffigan will drop in and then Todd Barry or Louie C.K. will do a spot in a setting where you don’t normally see those guys very often. Also in New York, you can do three shows in a night. You can start the week with a new bit, and if you’re throwing it out every night, you can figure it out by the end of the week in front of a lot of different audiences.

You have written for a number of television shows. Has there been a television writing job that was particularly important or enjoyable for you?

In terms of an experience I enjoyed the most, certainly my involvement in Letterman. He is kind of why I do comedy in the first place. And getting the internship there was probably the biggest thing that ever happened to me because it specifically brought me out to New York. Also, when you grow up watching something, it doesn’t seem like it should be feasible to be on that show. Even just going in on the internship interview  and seeing the people who had done on-air bits for the show — seeing [stage manager] Biff [Henderson] in person just walk around and doing his job was so weird. And then getting to hang out with those guys. They are nice people.

My affiliation with Letterman is certainly my favorite TV job. Getting Dave to tell your jokes is pretty neat. And then, finally getting to stand where he stands and do comedy from that spot. One phrase Dave has said a lot over the years, especially when he is doing something that seems particularly boring or stupid, is “this is the only thing on CBS right now.” Like he had a segment where he had a grape lowered into his mouth [with a fishing rod]. He just dealt with that for five minutes. It was fun for me to be “the only thing on CBS right now” for five minutes.


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