'Billy On The Street': Hilarious, Sure, But Also A Deep Pleasure

I’ll get to why I love Billy On The Street — season premiere Thursday night, now on truTV — as soon as I wipe away my tears of laughter at a second viewing of one of tonight’s segments, “Bob Dylan or Anal Sex?”

Billy Eichner has come to wider attention over the past year or so for his appearances on Parks and Recreation and the funny new Hulu series he co-created with Julie Klausner, Difficult People. But it was Billy On The Street —first online, then on TV — that made him a cult star. Eichner’s deceptively simple concept — running up to people on Manhattan streets and asking them pop-culture trivia questions — would have been a snooze were it not for Eichner’s style.

He’s manic and aggressive, yet an exceedingly adroit improviser who responds to people with full engagement. Although he likes to portray himself as eager for attention and celebrity, the key to Eichner’s on-screen charm is that he really listens to people, and wants to elicit their honest opinions about everyone from President Obama to Angelina Jolie. If he disagrees with someone, he’s likely to dismiss them with immense harshness that’s so exaggerated, even the insulted person frequently gasps a laugh at his energetic effrontery.

Tonight’s season premiere gets its biggest celebrity push from Tina Fey, who’s game to take on the challenge the host dubs “Latina Fey”: Fey has to name a dozen Latino performers in 60 seconds to win a prize (Brokeback Mountain oven mitts). Fey is plucky, but it’s a measure of how good the show is that her segment isn’t the highlight.

No, that’s the segment I mentioned up top, in which Billy accosts a couple of middle-aged-looking women and asks them to questions over the course of 60 seconds in which the answer is either “Bob Dylan” or “anal sex.” At one point Billy’s query is, “This can be so much fun as long as you’re in the right mood for it.” Both women answer, “Bob Dylan.” No! yelps Billy: “It’s anal sex.” You can see him pause for just a nano-second before he yells ecstatically, “Actually, it’s both — I’ll give it to you!”

There is a joy in what Billy Eichner does that makes On The Street exhilarating. It’s no wonder that, in David Letterman’s final weeks on the air, he agreed to accompany Billy for a citizen quiz: The notoriously uncooperative talk-show host recognized in Eichner something of himself in his early days, when Letterman used to take to the streets for silly stunts.

In addition to its humor, Billy On The Street is going to be, in years to come, one of those time-capsule TV shows you watch again to see New York City in the early 21st century: I love TV shows that, without calling attention to what they’re doing, film New York in a way that captures the look and feel of the ever-changing cityscape. (Look at a rerun of the 1960s sitcom Car 54 Where Are You? for an example of what I mean.)

Those two women who answer Billy’s questions — only in New York would you find two such women (who turn out to be mother and daughter) completely unfazed at answering questions involving the phrase “anal sex.” And only on Billy On The Street would that segment end up with the host planting a big wet kiss on one of those ladies’ lips.

Billy On The Street airs Thursdays at 10:30 p.m. on truTV.