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

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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.

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