Billy On the Street: How Michelle Obama Got on the Show

February 19, 2015 2:58 PM EST

Billy Eichner has bellowed at plenty of celebrity pals on his Funny or Die series Billy on the Street, but none more famous than Michelle Obama. This week the First Lady took part in a special edition of Billy on the Street (more like Billy in a Grocery Store) to raise awareness about her new healthy eating campaign, Eat Brighter!, a partnership between the White House, Sesame Street (whose very own Big Bird stopped by for the fun) and the Produce Marketing Association.

TIME spoke to Eichner about how it all went down, his upcoming Hulu show and what Zooey Deschanel was like in college.

TIME: How do you get Michelle Obama on the show? Does the White House pitch you? Do you pitch the White House?
Billy Eichner: Well, I would never be presumptuous enough to pitch the White House. Funny or Die, which produces Billy on the Street, has a good relationship with the White House and the Obamas coming off the Between Two Ferns that President Obama did with Zach Galifianakis, which was very successful.

I’m not sure who did the initial reach-out, but I believe it was someone on Team FLOTUS who knew that the First Lady was passionate about raising awareness of this Eat Brighter! campaign. They were looking to promote it in ways that would be entertaining as well as educational. It would be raising awareness among the parents, really, who are the ones responsible for taking their kids to the grocery stores and making decisions about what they eat and snack on.

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The First Lady had seen a bunch of my videos and thought that the combination of this campaign geared towards parents of young children and my energy and enthusiasm would be a good match. That way, we would be able to break through the clutter of what’s online and get people’s attention in a funny way. As soon as I heard this was a possibility I was incredibly honored to do it. I’m so glad that it worked out and people liked the video.

How much did you have to run by her ahead of time? Was she game for whatever?
That’s what’s really great about the First Lady. Billy on the Street really depends on spontaneous unscripted reaction. We’ve never staged anything or rehearsed anything. I made it really clear that as much as we wanted to do the video, in order to have the best results, we really should not run the questions by the First Lady. They’re not used to doing things that way, but they did allow us to do it. We did talk through general ideas of what we might do with her team, and we sent over sample questions, but none of those sample questions were used in the actual shoot. They were just in the spirit of something I might do. And she obviously had watched a bunch of my videos. When she got there, one of the first things she said to me was, “I really don’t have any idea what you’re going to ask me.” She was told that was the best way to do it, and she just went for it. She was game.

So she’s a true Billy on the Street fan, that’s not just her team saying that?
Well, she better be now! She wasn’t going to say yes to dealing with all of my craziness without being a fan of some of my prior work.

What’s the security situation like? If the cameras had turned out around, how many Secret Service people would we have seen?
I believe it was between 10-12 Secret Service guys. We were in a supermarket in D.C. that had been shut down to the public for the hour we were shooting. They swept it through, but once we were in the room, the Secret Service guys were very cooperative. We talked them through a little bit about what we’d be doing so they wouldn’t shoot me if I decided to run in a particular direction.

I figured they probably blindfolded you and drove you around in circles first, Homeland-style.
That’s a whole other game I hope to play one day on Billy on the Street.

Was Elena always going to be a part of it?
Bringing Elena into it was my idea. One of the things we weren’t able to do with the First Lady for obvious security reasons was take her out onto the street and run up to people. And because the point of the video was to raise awareness of a campaign in grocery stories, the First Lady’s only request was that we shoot in a grocery store so people could get some sense of what the Eat Brighter! campaign actually looks like. So how do we do all of that but also maintain the spirit of Billy on the Street which does involve spontaneous reactions from a real person?I thought, what if we could bring someone to the store?

Elena is everyone’s favorite contestant on the show. One of the great things about Elena is that no matter what you throw at her, she’s pretty unfazed. I also knew from prior conversations that I had with Elena that she loves Michelle Obama. She once said if she could have dinner with anyone, it would be Michelle Obama. So I thought it would be a good idea, as long as we could bring Elena down without her knowing who she’s going to meet. Team FLOTUS agreed with that, and some of my producers escorted Elena down to D.C. We had her sequestered in a room in the grocery store before the First Lady got there. Once we brought her out, she was blindfolded, she had earplugs in. The reveal that you see on camera is exactly how it was.

I love that Elena didn’t even believe it was her at first.
Yeah, which makes sense to me — she’s familiar with other weird stunts I pull on the show, so it wouldn’t be out of the question that I would get an impersonator or something.

Has Ariana Grande seen the video?
I don’t know, that’s a very a good question. I thought she’d get a kick of it.

I think she has a good sense of humor.
I think she does! We’re not terrible snarky to Ariana Grande. I go out of my way to say she’s a good singer. The only thing is Elena points out that her ponytail is fake, which is another perfectly Elena thing to say. But I hope she sees it and likes it. Or at least Frankie Grande. Give me something.

How’s your Hulu show with Julie Klausner coming along?
I am sitting in my trailer right now as I talk to you because we are in the middle of shooting it. We’re about halfway done, maybe a little more. It’s going to be eight episodes on Hulu. We haven’t been given a premiere date yet, I think it’s something like late summer or early fall. We’ve been shooting in the incredibly cold New York City temperatures, but we’re having a really good time. Amy Poehler is the executive producer, and there are a bunch of guest stars that haven’t been announced yet, so I don’t want to get in trouble and say who they are. There are some really great comic actors whom we all know and love making appearances on the show, playing my family members or themselves in various cameos. It’s about two thirty-somethings still trying to make it in the entertainment industry. There’s a lot of pop culture talk, but it’s pop culture with a very strong point of view. It’s coming from, I hope, a intelligent perspective, as opposed to some of the more derivative stuff.

Zooey Deschanel recently told me a story about how you both did A Funny Thing Happened on the Way to the Forum together in college. Do you remember that? What was she like in college?
She was great! I did an episode of New Girl with her a few months ago, and it was very much a full circle moment because the last time Zooey and I had performed together was when she was a freshman at Northwestern and I was a junior. We were both theater majors cast in a student production of A Funny Thing Happened on the Way to the Forum, and I played her pimp, essentially. I mean, it’s about ancient Roman times, so there are nicer words for it than pimp. I remember her in college very vividly, she was really funny in the show.

She had a great style back then, which was really unusual because Northwestern has a lot of theater majors who show up to class in jogging pants. There isn’t much of a personal aesthetic — it’s the Midwest. Now she’s somewhat of a fashion icon, and that’s not surprising to me. She was always like that, even when I met her years ago.