Billy Eichner on 9 Great 'Billy on the Street' Moments
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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.