Sarah Jessica Parker and Billy Eichner from Billy On The Street season four (Screenshot: TruTV)

Billy Eichner has catapulted from making a series of YouTube videos to his own Billy On The Street, which has provided four delightful seasons of him accosting strangers on the avenues of New York City and asking them random pop culture trivia questions like “Jon Bon Jovi: Sho ’nuff or no he didn’t” or “Bob Dylan or anal sex.” More recently he’s added the bonus of celebrity guests, in case people wanted to see Julianne Moore randomly act on the street or find out whether Sarah Jessica Parker knows the difference between a reindeer and a sex app (she does). At the summer Television Critics Association conference in Los Angeles, it was announced that Eichner’s take on the man on the street will return for season five this fall, featuring celebrity guests like Jon Hamm, Aziz Ansari, and Lupita Nyong’o.

In the meantime, Difficult People, Eichner’s Hulu sitcom with Julie Klausner about two acerbic people in New York struggling to get into comedy, has recently kicked off its second season. As it was recently established that the snarky, pop-culture-laden Difficult People is the perfect show for the A.V. Club viewership, Eichner sat down with us for a few minutes to chat (yell) about why that is so and how all those quizzes happen on Billy On The Street.

The A.V. Club: Did you agree with our article that Difficult People is the perfect show for our readership?

Billy Eichner: I tweeted it out and everything. I thought it was great. I was flattered. You guys actually got it. It was good.

AVC: It helps that the show has a TV recapper as a character.

BE: Exactly. If you’re not going to get it, I don’t know who’s going to get it.

AVC: Besides A.V. Club people, what other types of people do you think the show appeals to?

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BE: Difficult People? I don’t really know. I don’t have those metrics. But it seems that with the second season, we’re kind of getting into people’s bloodstream a little bit more. We only had eight episodes the first season. It was over the summer. It was one of Hulu’s first original shows to really go out there. Now a year has passed, and the second season is getting a great response. I think the show itself creatively has evolved, has gotten much richer and tighter. We’re really fleshing out the whole world of the show. It’s more of an ensemble now, whereas last season we were very focused on establishing the Billy/Julie friendship. Now that that’s been established, we don’t question that they love each other and what the show’s about. So we can meander outside of that.

All I know is that the response has been really great. I think it’s for smart people. I think it’s for people who obviously care about pop culture or know about it, even if it’s to a fault. I think it’s for outsiders. I think it’s for people who don’t feel that they have been properly represented on TV. I think it’s painting a very accurate if slightly exaggerated for comedic purposes view of the LGBT world in a way that we have never, ever seen in any television show. These characters are multilayered, the gay characters: They’re funny, they’re cruel, they’re sweet, they’re horny, they fuck, they hate people, they love people. They’re neither evil villains nor self-righteous angels. There’s gray area there, the way there is with any type of person. That, to me, especially in the second season, is really important. I wish more people talked about that. I think they are in their own circles. I don’t know if anyone’s written about that. But I don’t see any other show doing that.

AVC: Does that experience of you and Julie mimic your own experience? You see those two, they’re so funny, but they’re like a niche market. But now you two have gotten pretty successful with the same niche market. How does the show trace your path to where you are now?

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BE: In certain ways, the Billy/Julie characters are less proactive and less self-aware. Even when I was struggling and had horrible day jobs and wanted to be successful but wasn’t finding my way in, I knew what I had to do. I knew I had to keep working at it and keep putting material out there, even if no one was paying me for it. That I couldn’t just get up every day and be miserable and complain. But part of the fun of the characters is that they’re so bitter. Not that I didn’t have my bitter moments, but for the most part, I was very proactive and had my eyes on the prize, and Billy and Julie, they have their eyes on the prize, but their lack of self-awareness makes it very hard to achieve any goal. They’re always getting in their own way. Then sometimes the world gets in their way, and then they react to that, and it only fuels their anger and desperate need for success.

Does it mimic my trajectory? Only insofar as that I was still kind of not successful in my early 30s and really feeling like, “Oh, boy. It’s got to happen soon.” But I wasn’t as dumb as they are. That’s really what it comes down to.

AVC: I’m so curious about the amount of work that has to go into Billy On The Street. Like all the quizzes. How does that happen?

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BE: You’re one of the only people who’s ever mentioned that. I don’t know why, but it kills me. You don’t want to do an interview and talk about, “Oh, I have so much work to do.” If you’re on TV, you can’t complain, right? And I understand that, and it’s true to a certain degree. But as long as you’re bringing it up, it is… No one will ever understand. By TV standards—I’m not comparing it to manual labor by any means—by TV comedy standards, it is the hardest job I will ever, ever have. There is nothing that could be harder. I mean, when you combine the amount of writing that has to be done—sharp writing—with the fact that you then take it to the street and improvise with both celebrities who have no idea what’s going to happen and real people who are not actors or comedians who don’t even know I’m about to talk to them… It’s lightning in a bottle every time. And the camera guys can’t mess up. God bless them, they hardly ever do. But they literally don’t know what’s going to happen next. None of us do. And it all has to come together and be funny.

It’s crazy. I don’t know how I’m not dead. [Laughs.] People think I’m going to get punched in the face: “Something terrible is going to happen to you. You’re going to get killed.” That’s not what’s going to kill me. The show is going to kill me. The work is going to kill me. Once I’m on the street, I’m not worried about that.

AVC: Like, the idea behind OKCupid: One’s a reindeer, one’s a dating app…

BE: I wrote that. I remember thinking that Santa’s reindeers’ names sounded like apps to me. That Tinder sounded like Donner, and Cupid like OKCupid. Grindr sounded like Prancer. They weirdly sounded alike to me. And then I Google apps and Santa’s reindeer, and I see the names, I pair them together, and there’s the game. That’s easy though. That’s easy compared to some of the other things.

AVC: What are some of the harder ones? Facts about Jon Bon Jovi?

BE: That’s easy, because that’s just facts. That was early on. Now we really push ourselves to come up with clever shit. Oh, like “John Mayer or Pepé Le Pew.” You really have to work to find the right quotes. Just any old quote won’t do. You’ve got to find Pepé Le Pew quotes, and then you have to find the John Mayer quotes that sound like they could be Pepé Le Pew quotes.

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Because that’s the whole joke. Something about John Mayer, who I’m a huge fan of, by the way, his whole Lothario persona…

AVC: Your previous “penis, no penis” quiz about who had actually dated him…

BE: Yeah, all of that. How much he used to—he’s scaled it back now, I think. There was a period where he was really out there on the scene. And I thought, “He’s like Pepé Le Pew to me, running after these girls. His heart’s getting crushed, and then he’s out there again.” It was a funny comparison, but it won’t be funny if you don’t find the right quotes. There are other ones that are harder. But it is an enormous amount of work, and we really work at it.

AVC: Do you do most of that yourself, or does your staff come to you with an idea?

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BE: It’s me and a team of five or six writers, and we have about seven weeks of preproduction where we try to figure out as much as we can before we start shooting.

AVC: People probably expect you now in New York.

BE: I can tell when somebody recognizes me, and I try to avoid those people. I don’t think the show would work as well.

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AVC: I’m sure you’ve been asked this before, but what’s the most outrageous thing that’s happened to you when you accosted somebody on the street?

BE: The most outrageous thing happened years ago in my YouTube days, when I asked an older lady—it was like a sexually flavored question and she just slapped me full-on across the face. That’s the one time someone got physically aggressive with me. And it hurt. And she had a right to, and I loved it, but that always sticks out in my head.