Many have noted the conversational style of John Mulaney’s comedy. His delivery is so natural that it doesn’t even seem like he’s telling jokes. Rather, it’s as though John is telling the audience about a funny thing he saw the other day, just as he would if he saw the audience at a party or ran into the audience on his way to work. That’s because that’s exactly what John is doing. After years of digesting comedy, John’s sense of what’s funny about the world has become so finely honed that he’s able to perfectly convey what’s humorous about the world around him.

The ease with which John explains the world’s absurdity is deceptive. On The Top Part, John’s first release, he presents a collection of 14 tracks that were honed over countless nights with the precision of a diamond cutter so that, in the end, John’s portrait of Donald Trump, for example, is so accurate and succinct that all of Trump’s millions cannot free him from John’s analysis, which paints him with a few strokes with more accuracy than all of Trump’s books and television appearances combined. It’s for this reason that John finds himself writing for SNL and Important Things With Demetri Martin, making appearances on Conan and many more projects that, soon enough, will furnish the world with tremendous laughter.

Ben Kharakh: What are some of your earliest memories of seeing or hearing things that made you laugh?

John Mulaney: I watched a psychotic amount of TV and movies when I was little, and my parents showed me a lot of comedies, like The Producers and The Marx Brothers. My dad would buy me lots of different comedy tapes, like the George Burns Collection.

BK: On your Walkman? You would just go on a walk, listening to these comedy albums?

JM: I would just listen to a lot of old radio shows on my Walkman when I was a kid, and my brother and I, when I was 10, 11 and 12, really got into Monty Python and Woody Allen movies, and Caddy Shack and Animal House and Kentucky Fried Movie… Around the same time, The Simpsons was in its heyday and Conan O’Brien had just started at midnight, so I watched all that, but at the same time, I still listened to a lot of the comedy from the ‘30s and ‘40s, back when you had to buy 30 VHS tapes. I had a lot of Jackie Gleason and Honeymooners and I Love Lucy, so I really liked comedy from the ‘30s, ‘40s and ‘50s when I was growing up, and at the same time was getting into a lot of later stuff.

BK: I read that you mother had signed you up to do sketch and improv at seven, but I’m curious if prior to then you had shown an attraction to performing comedy yourself…?

JM: It was like half performing comedy, half just kind of performing, and since you’re five, it is comedy. I would act out episodes of Dance Fever, the Denny Terrio show, for my parents and their friends and stuff. I don’t know if I knew it was comedy at the time. I’m sure it was because I was just a weird little boy dancing around. But yeah, I was always aggressively looking for attention. At school, they would tell us, “Okay, you can do a diorama or a skit or a project.” They would just have this option. It was like, “You can write a two-paragraph thing on this book or you can do a diorama on this book or you and some other people can present a skit on this book.” I always chose to do something that we could act out, so some other mother heard about this thing run out of a small theater in Chicago and was like, “Hey, your weird son might like this.” So my mom signed me up for it and I went for like three years when I was seven, eight and nine, I think.

BK: This is the second time you’ve referred to yourself and perhaps others calling you weird. Is that a thing that people were actively doing?

JM: I wasn’t constantly being called weird, but I was kind of a spastic young man. Yeah, I was weird, I guess. I really liked Frank Sinatra when I was 10, and my 11th birthday present was going to see Frank Sinatra at a casino outside of Chicago. I remember asking my mom in the kitchen why my brother and sister were making fun of me, and my mom was like — I think she phrased it nicely — “You’re very unique.”

BK: What were you like in school?

JM: You know, good at some things, not good at others –- good in English, bad in math. I was talkative and teachers always liked me. I could be lazy, though. I certainly wasn’t an overachiever in every subject.

BK: What sort of things did you do to get laughs from students, teachers…that sort of deal?

JM: Well, one of the first stand-up comedian jokes that I heard where I thought, “Oh, that’s really true,” was George Carlin’s joke on the Class Clown album where he’s talking about how there isn’t just one class clown — there are a few. That immediately struck me as true. I had two friends, who were also named John, by the way, and we would do bits together. I remember my parents having a party once, and I had watched a Dr. Ruth special on TV, and I came down and started repeating everything I had heard on it for them. Someone asked me what I wanted to be and I was like, “I want to be a sex therapist because sex is an experience in life and it brings joy to the body.” I remember that going over really well. The Johns and I were constantly fooling around. I remember my friend John O’Brien’s dad once said to us, as we were just sitting around being idiots, “All you guys do is just amuse yourselves all day long.” I thought that was really funny back then, and I still do. It was very true. We were constantly messing around. We were McCarthy, Mulaney and O’Brien, so alphabetically we were always right near each other too.

BK: Did you have a special name for this trio of three Johns?

JM: [Laughs] Yes, we called ourselves the three Johns, but not as a troop. We didn’t do shows and advertise them or anything. I remember when we were nine years old, we got sat at the same table again. My friend John McCarthy came up…it was like the first day of school. We all got seat assignments, walked over, and there’s the three of us sitting next to each other again, and he says, “Alrighty, three Js, hanging ten.” And that cracked us up a lot. Wow, I haven’t repeated that in about 16 years.

BK: Did you ever get in trouble for any of this?

JM: Not really, no. I still wanted every teacher to like me, and I knew how to be a good kid. If it ever tilted too far, I knew how to back-pedal and apologize really quickly. I was very conscious of the fact that I lived very close to the school and that my parents were very involved in the school. It was a really small grade school community. I always felt like I had something to lose by screwing around too much. I was super annoying in that way. I did a lot of bits and screwed around, but then still wanted the teachers to like me. What a portrait of an annoying young man!

BK: Where is it that you would draw the line then?

JM: I didn’t want to be disruptive. I wanted to be really funny, but if we got warned, I would quiet down. I didn’t want us to get shut down. I didn’t want us to get split up and for our show to get canceled, so I would play ball. I didn’t want our seats to be moved around. I didn’t want to have to go wait in the hall. I wasn’t going to let that happen. I just wanted to get the bits out there.

BK: When was it that you decided a career in comedy or in entertainment was what you wanted?

JM: I always wanted to be an entertainer. I took drum lessons when I was a kid because I thought I wanted to be a bandleader, but that didn’t last too long. When I was young, for a while I thought I wanted to be an actor or something. It was always some variation of being a performer, but I always wanted to be an entertainer of some kind.

BK: While you were making all these jokes growing up, did you ever start memorizing them to repeat later or to write some of them down?

JM: Sometimes I would come up with bits at home and try them out at school. I don’t know what they were — just lines. I’d just write them down and bust them out at school.

BK: Did you have any officially sanctioned creative outlets or were involved in any clubs like student council?

JM: I was student council president when I was in eighth grade, but I had a very serious campaign. I wanted to be really funny all the time, but I also felt I needed to be taken seriously. We had what were called the Spring and Christmas Concerts every year, which were basically pageants, so there were songs with little banter in between and sketches and stuff. To me, it was our variety show. Me and my friends would take them over and either host or I hosted solo one year, and we came up with a bunch of material for it. It was really fun. We would get out of class to do that. We’d just say, “Yeah, we’ve got to go work on the concert.” We were in junior high and we’d somehow finagle out of class. I can’t believe we were able to do it. It felt like we were always working on these big school concerts and trying to do things with them. I hosted one year when I was 11 as Ed Sullivan, and then John and I hosted the year George Burns, Dean Martin and Gene Kelley died — we hosted as the three of them. We just worked for what felt like a month — it was probably a week. We worked for a week on all the different introductions for the different grades and having little bits in between classes singing their songs. It was really fun.

BK: Were the other students as knowledgeable of George Burns and Gene Kelley as yourself and your friends were?

JM: I had another friend who loved I Love Lucy and Frank Sinatra too. We were the two kids who, when we were 11, really liked Frank Sinatra and Fibber McGee and Moll, so we were constantly absorbing that stuff together.

BK: What sort of campaign did you run to be the president?

JM: I don’t remember, but it wasn’t a very creative, funny campaign. It was just, “Hey, I’m a good boy. Vote for me. I’m a good person.”

BK: How did you imagine yourself getting involved in a career in comedy and entertainment?

JM: Well, first of all, I thought you could still be a bandleader, so I didn’t really know. And then I read a lot about Woody Allen and Steve Martin and the Marx Brothers and stuff. I kind of remember realizing there was no longer Vaudeville and thinking, “Uh oh. What am I going to do? How am I going to get my start?” But I was pretty aware of being able to go see a stand-up comedian or being able to form a sketch comedy troupe and start performing. There were a few books that were out about Python and the like, so I read them, but I didn’t have an exact battle plan. I kind of knew, if you want to be a comedian performer, there are a couple of avenues. I don’t remember how realistic my ambitions were after I realized I wasn’t going to be the bandleader at Copa Cabana, but I knew of some real avenues I could take.

BK: What made you realize you weren’t going to be the bandleader?

JM: I do remember a lot of people not knowing about Desi Arnaz. I remember my friend had to do a report on mambo music when we were 11. He wasn’t able to find any books at the school library about the mambo wave of the ‘50s, so we slowly realized that maybe it wasn’t going as widespread as we thought. It’s a constant disappointment to me that we don’t live in the ‘30s and ‘40s, but I deal with it day in and day out.

BK: Now that you are a performer, when it comes to writing your material, where on the spectrum of sitting down and writing beforehand and improvising a lot of it on stage do you place yourself?

JM: In between, but closer to the writing side. There was a period, before I was writing for Demetri Martin’s show, where I was doing at least one set every night, if not two. So during those times, I’d say I would improvise more on stage, but that was because I had so much stage time at the time prior to that, and now I think I have more written-out ideas. The less sets I feel that I have, the more I feel the need to have things  hammered out when I go on stage.

BK: When the time came for you to transition from being a performer who was aspiring to perform to one being booked at shows, to one who was being paid to perform, was there any change in how you approached comedy once income was involved?

JM: When I first moved to New York, I was temping a lot. I was doing sets a couple times a week and trying to figure it all out. I never had a backup plan, so it was always the same mindset. It was just what I was doing. But after about a year in New York, I was thinking, “Oh, just do every set possible — get up every single time you can. Don’t be selective about anything. Just go up, go up, go up and work on jokes and go up.” What was important was the shear volume of stage time. Go up constantly, you go up somewhere, you meet someone at that show who runs another show, and then you get another spot through that. Then I started the show with Nick Kroll, and now I have one weekly spot I know I can always do stuff, and people come and do our show and then they invite me and Nick together and individually to go and do their show. There’s no other way except going up constantly. I’d say that the jumping-off point for me was around the winter of 2005. I no longer had any kind of day job. And then that February and March, I went on Comedy Central’s college tour with Mike Birbiglia. That was so many shows — that was 30 days on the road straight, with colleges and clubs in between those days. In between college days, we would do a club for a night, so it was at least one show a night, sometimes two shows a night. I’d say before that tour, a part of me always hoped the show would be canceled, but after that tour, I would be disappointed if I didn’t get to do a set.

BK: Why were you thinking about the show being canceled?

JM: I didn’t have severe stage fright or anything, but I would just think, “Oh gosh, I want to do this show…but do I? I’m nervous. There are going to be a lot of people there.” It’s just hard to get up. It’s just hard at first sometimes. I had already done a lot of sketch comedy and stuff. I felt comfortable on stage, but I’d still think, “Okay, now I’ve got to actually do this.” After a certain point, I was doing so many shows on that tour, and after that I thought, “I want to get up because I want to work on that joke. I want to get up tonight because I want to try this and that, and I put that in a new order and I want to see how it goes,” whereas before, it was, “I want to be a comedian. I booked my show. I have to go up and do it.” I say around that time, I just got very obsessed with doing it — not in the abstract, but in the here and now. Like, “Oh yeah, okay, now I’ve got 15 minutes that I like. That’s great. I just booked myself to do 25 minutes. Okay, I’m going to have to figure out how to do 25 minutes. I’m going to have to write more stuff, try new stuff. Okay, I only have 20. Maybe I’ll try to make up some stuff when I get to the club.” It became about doing it in the real world versus, “Oh wow. I’m going to New York and becoming a comedian.”

BK: Were you conscious of not having a backup plan?

JM: I think I was conscious of it, but it wasn’t like, “Uh oh, I don’t have a backup plan.” It was more of, “This is what I’m doing.” I don’t think I thought of it as the absence of a backup plan; I thought of it as a presence of a plan.

BK: Was there ever any sort of inner debate or wavering about whether or not you could do it or not?

JM: I remember thinking it was going to be hard. I remember, very early on, not getting it that if you do a show and do well, nothing happens afterward. The first few months of doing stand-up in New York, when I was still in college, I was an intern in 2003. You think, “Wow, I did really well last night. Something will come from that.” Yeah, what will come from that will maybe be another set somewhere. You did a good set and you can figure out what jokes work. Become a better comedian. So you keep doing it and work really hard, but I don’t remember it being that scary. Shows can be scary, and when I started going out on the road, that was scary and I thought it was something very new — being in a new city and now you’re staying at a hotel. You’re emceeing or featuring, you’re being paid and expected to do well…that was frightening, but it was just anxiety. It wasn’t like truly scary, like I made a mistake career-wise.

BK: With all these exciting projects in the works and all these exciting prospects, how are you feeling about all this?

JM: I am very fortunate to be able to work on these types of things and have these opportunities this early. I’m very aware that I was able to do some of these things early on, and that’s really fortunate. So it’s really exciting. I’m definitely aware that I’m incredibly fortunate. Who knows what will happen? But it’s really fun right now. I always wanted to be a comedian and a comedy writer, and now I get to do that.