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Billy Eichner on 9 Great ‘Billy on the Street’ Moments

From Michelle Obama’s shopping-cart ride to Lindsay Lohan’s auto destruction, comedian gives us the scoop on nine memorable ‘Billy’ bits

Billy Eichner on 10 Great 'Billy on the Street' Moments

Art Strieber/truTV

It used to be that man-on-the-street shows were a dime a dozen — that was, at least, until Billy Eichner came along. The host of cult sensation Billy on the Street is known for his signature interview style, which falls somewhere between the gossipy best friend you just met and a rabid attack dog. Each episode of Tru TV's comedy game show features Eichner running up to strangers on the sidewalks of Manhattan and asking them questions like, "Are you jealous of Beyoncé's success?" or "Who's weirder: Tom Cruise or John Travolta?" If he agrees with the answer, he'll give them a dollar; if he doesn't, he'll scream at them and storm away. (Don't even ask about "Quizzed in the Face.") Sometimes, a celebrity – Will Ferrell, Tina Fey, Chris Pratt – or his sidekick, a cranky sixtysomething named Elena, tag along while he does his his disruptive shenanigans. Other times, he’ll just let Lindsay Lohan takes a sledgehammer to a car covered with pictures of the How I Met Your Mother cast.

With the show's fifth season kicking off tonight, we caught up with Eichner to get the backstories behind some of Billy on the Street's most memorable moments – from a Shonda Rhimes–themed obstacle course to a supermarket outing with First Lady Michelle Obama.

Art Strieber/truTV

The Julianne Moore Acting Attack

Every time we book a celebrity, I think: What do I want to see that particular person do? It's either something out of their comfort zone, or it's taking something about their essence and flipping it on its head. With Julianne Moore, I thought, well, she has an insane list of IMDb credits of great performances going back 25 years. I want to see her act.

Our production office that year required me to walk through Times Square, and every day I would see all the fake off-brand Elmos and Spider-Mans trying to get tourists to take pictures with them for tips. And it just came to me: I’m not into superheroes and I’m not into animated movies, but I’m into great actors and indie films. I thought: Julianne Moore is my Spider-Man. So what if we put her in this context — acting for tips? It was all about her delivering monologues from various movies and really acting the shit out of them. And she was totally game.

When we first got there, she was really rushing through the monologues. I was a little worried, because who am I to give Julianne Moore an acting note? But I did say to her at one point, "Take your time with it, and really deliver it as you would in character and go through the emotions of it." Her skill set is just so evident when you watch it. The way that she's able to dive into those roles again, and really hit these very nuanced moments in the middle of this very frantic segment. She was so committed to it. I was so thrilled to have her.

Art Strieber/truTV

Lindsay Lohan Destroys a Car

The news out of Lindsay's world wasn't so great at the time – but I was not looking to exploit her private life or do anything tabloid-y. I wanted to make sure that we treated her like we would any other celebrity. She was filming her reality series on OWN [Lindsay], and we let them film us filming the segment. It was very meta and odd, but we said, "As long as you don't get in our way, it's fine." And they didn't, for the most part.

How I Met Your Mother was ending at the time, and for some reason I thought it would be random and funny for Lindsay Lohan to be really upset about that. So we decked out a car with pictures of the How I Met Your Mother cast, and Lindsay and I destroyed the car as a way for us to unleash our anger that the show was ending too soon … even though it had been on for nine seasons. I remember it being very physically difficult. It took some strength. I was worried whether she'd be able to do it, but she actually had an easy time with it.

I did start bleeding — some of the glass got onto my hands. And I was like, "Wow, we had Lindsay Lohan on the show, and I started bleeding? Who knew?" [Laughs] I'm kidding. She was a good sport. We do depend on the celebrities to allow me to have my way with them creatively. It really wouldn't work if they weren't willing to.

Art Strieber/truTV

‘Quizzed in the Face’ With Elena

Elena is really the quintessential New Yorker to me. I don't think she’s aware of how funny she is, which of course makes it funnier. I approached her without any preparation or any premeditated ideas of who she was. To me, she was just another person walking down the street. But from the second Elena started talking to me, she was just hysterically funny. She wouldn't take any of my bullshit – she gave it back to me as hard as I give it to people sometimes.

I never wanted to be one of those shows that brings back everyone's favorite contestant. But I just loved Elena so much, and the viewers loved her so much; now she’s part of the Billy on the Street family. She's so unfiltered and opinionated and so, like, disgusted and passionate and easily flustered. But she also has this great reserve of strength and determination. So we brought her back and did all sorts of things with her. She played against Lena Dunham, she played against Michelle Obama and Big Bird – which was obviously a huge moment for all of us.

Elena is really what Billy on the Street is all about: She's a lady of a certain age who lives alone in New York, and she really has lived life by her own rules. She's really passionate about what she believe in. We often get into tiffs on the show, but I love it. She really makes me laugh.

Art Strieber/truTV

Billy’s Thanksgiving Day Parade (With Katie Couric)

The Thanksgiving Parade was an enormous undertaking, particularly for our little show. I grew up watching Katie Couric host the real Macy's Thanksgiving Day Parade, so we asked her to co-host with me, which really helped to sell it. And she was really good at it – really dry and not winking to the camera at all.

The floats were all made here [in New York]. No one realizes how complicated Billy on the Street is. We've done a good job of keeping it looking kind of raw and low-budget. But we have a whole art department and a whole production studio. We have construction workers and people designing things and building things. Every prize, every costume, every obstacle course, goes through a series of drafts. It's a huge process.

We designed the balloons here, but we found the actual people who make the Macy's Thanksgiving Day balloons, who I think are in Hong Kong. So we had the balloons made there. They don't speak English, so we had to send someone who speaks Chinese over to communicate with them. It was months and months of these people in a random town in China, building a huge balloon of Maggie Gyllenhaal. It's the height of absurdity. It will never get more absurd. But I'm so glad we did it. That segment is one of my favorites. And who else is going to make a United States of Tara float, for better or for worse?

Art Strieber/truTV

Shopping With First Lady Michelle Obama and Big Bird

When they first reached out to us, I thought it was spam or something. And then Mike Farah, who's our executive producer, emailed me and said, "Hey, did you get the email from the First Lady's team?" And I said, "I deleted it. Like, I didn't even read it. I thought it was a joke or something." He said, "No, you're an idiot. It's real. It's from the First Lady." Turned out to be the real deal.

The Obamas have always been very savvy and successful when it comes to figuring out how to actually get the word out to people, particularly young people. And a lot of that happens through creative enterprises on TV and the Web. They wanted to promote this Eat Brighter campaign that they were working on with Sesame Street – hence the presence of Big Bird – and they wanted it to take place in a supermarket.

But I didn't want it to be: Oh, we have the First Lady in the video and that's enough. For her sake and for our sake, it needs to be legitimately funny and it can't seem diluted. The questions cannot be scripted. She cannot know what I'm gonna ask her to do, because that's the magic of Billy on the Street. And just because she's the First Lady and just because Big Bird is Big Bird doesn't mean that we can deviate from that now.

When she got there that day, I was insanely nervous. But she's the loveliest and the smartest and the warmest, so down to earth. She showed up in a sweatshirt and jeans ready to play. The first thing she said to me was: "Okay, I was told I can't know anything, so I don't know anything about what you're gonna do. I'm trusting you." And I said, "We've got this."

There were a few physical challenges I had her do, like she had to push me in a shopping cart while I recited Gwyneth Paltrow's Oscar speech. Again, she didn't know about any of that in advance. But I did have to tell the Secret Service beforehand that I was going to ask her to move and to run, because they need to know where she's going. That's their job. I didn't want to get shot.

I ended up going to a State Dinner at the White House back in April, and I was there with the Obamas and David Letterman and Will Ferrell, and, strangely, all the Nordic leaders. It was very surreal. You walk through the line where the Obamas greet you one by one, and the First Lady gave me the biggest hug and said to me, "Wow, you've lost a lot of weight! Don’t go Hollywood on me, now." [Laughs] It was just so over the top. It was obviously a highlight of my life. I've been thinking about the Obamas a lot the last few days.

Art Strieber/truTV

Shondaland With Amy Sedaris

Shondaland is the name of Shonda Rhimes' company, and I thought, what if it was an actual destination? That was the germ of the idea, and then we decided that we could make that into an obstacle course. All the writers took a look at the various tropes that you find running through Shonda's work, and then thought about how we could turn those into these ridiculous obstacles. And we got Amy Sedaris, who I've always loved, to run it.

We were beginning to dip our toes into more socially conscious commentary – there's one obstacle where she has to run through a bunch of white people patting themselves on the back for embracing a black lead. It's still a bit gentle … or not, I guess, depending on your perspective. Aesthetically, it still fits into the very silly aesthetic of the show. I grew up obsessed with Double Dare and Pee-wee's Playhouse. So a lot of those games are inspired by the things I loved as a kid.

Art Strieber/truTV

Christmas Carol Ambush With Amy Poehler

I'm one of those Jewish kids who always wanted to be able to celebrate Christmas, so I'm a big sucker for Christmastime. We always do some holiday segment. Amy, of course, was as game as ever. Amy and I are obviously close because of Parks and Recreation and Difficult People — though Difficult People wasn't around in those days.

That became a running theme of Billy on the Street: bringing these very famous performers out onto the street, shoving them in people's faces and getting real-time reactions to them. The assumption being, of course, that people are gonna scream and go crazy at the prospect of meeting a famous person. And there's a little bit of that. But usually it's New Yorkers going about their day who just couldn't give a shit, which I think is so great.

And it's shocking sometimes to the actors themselves. One of the first versions of that we did was with Zachary Quinto, and I ran up to people and pointed to him and said, "Miss! It's Spock! Do you care?" Some people were happy and some people didn't care. Other people didn't believe it was him. There was one guy who kept repeating, "That's not Spock. That's not Spock." And Zach looked at me after we shot it and said, "Every actor should have to do this." I think it's healthy for people to see that the average person isn't really thinking about actors very much.

Art Strieber/truTV

‘Weekend at Bernie’s’ or ‘Django Unchained’?

We shot another game that day with Will Ferrell called "Scream for an American Girl Doll," and it was Will versus all these little girls to see who could scream the loudest. We had brought this girl [named] Annelise there to play that game – but we realized we had one too many girls, so we cut her out of it. I said, "Alright, let's make her feel better. I feel bad. Let's play a game with her." So I chose "Weekend at Bernie's or Django Unchained?", and she bizarrely answers everything correctly. I don't know if she was able to just figure it out through context, or whether she just guessed. But she was very charming.

I never want the show to be about exploiting people – you know, exploiting children, or people who are not mentally all there. There are a lot of other man-on-the-street things where you can find people doing that, and I like to think that we don't spend the majority of our time making fun of less intelligent people. But this year on the show, we have Jacob Tremblay, the little boy from Room, who is honestly one of the most intelligent guests we've ever had. He's brilliant. It's like walking around with a 45-year-old man.

Art Strieber/truTV

Mr. Singh Gets Quizzed in the Face

Other than the Elena segments, my favorite "Quizzed in the Face" was one early on with this Indian man named Mr. Singh. Billy on the Street is often a case study in: Don't judge a book by its cover. If someone is dressed in a certain way, I think, Oh, they're going to be really loud and opinionated. But then they have nothing to offer and they completely shy away from the camera. Then you walk up to people who seem like they might be shy or boring, and we have a really funny interaction and they end up being very opinionated. Or there might be an elderly person who you don't think is gonna know a certain pop culture reference, but it turns out they saw that singer on Good Morning America that morning and they have a ton to say about them. So that's really the fun of it.

Mr. Singh was this middle-aged Indian man wearing a turban, and I did not expect him to know much about pop culture. But he knew a ton about Lindsay Lohan and Tara Reid and Shannen Doherty. He said such funny things about them, and he's so charming and so likable. It sounds cheesy, but it really is one of those "only in New York" moments. It's something that you want to happen, but you don't think will actually happen.