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‘Billy on the Street’: 10 Classic Clips to Get You Ready for Season 5

Actresses, obstacle courses, parades, masks and of course, questions answered for a dollar.

Billy Eichner and Julianne Moore in "Billy on the Street."

Billy Eichner and Julianne Moore in “Billy on the Street.”

Turner

Billy on the Street” is TV’s adrenaline shot. Whether the hijinks come from the show’s growing list of guest stars or the flabbergasted hoards of New Yorkers who become putty in the hands of a raving, microphone-wielding Billy Eichner, it’s a tried-and-true formula that’s birthed four full seasons of Manhattan-set surprises. The kinetic, chaotic game show hasn’t yielded any giant cash prizes or faraway vacations, but every episode turns a few random city folks into potential viral superstars.

READ MORE: ‘Billy on the Street’ Reveals Season 5 Guests, Filming Secrets

In recognition of the show’s storied history (Fuse’s Season 1 finale featured a member of Blink-182, this season on truTV opens with Jon Hamm, Seth Rogen and Lupita Nyong’o in back-to-back-to-back episodes), we’ve compiled a greatest hits of sorts, singling out some of the “Billy on the Street” moments we keep coming back to. (The descriptions below are not written in all caps, but please feel free read them that way.)

Elena!

Season: 2
What Made It Wonderful: envisioning “Lorne Michaels” as the hypothetical subject of “Run the World (Girls)”
Standout Moment: A legendary figure, Elena is the glorious antithesis to the manic energy that fuels “Billy on the Street.” That the show would randomly stumble on someone whose willingness to play along with the show’s signature antics somehow overlaps with a sublime stubbornness against every attempt to find common pop culture ground (“I’ve never even heard of it”) is nothing less than a feat. This opening salvo led to a number of recurring appearances for Elena, including a truly surreal game of “Cash Cow” against Lena Dunham that effectively broke Billy.

Rachel Dratch and Robstacles!

Season: 2
What Made It Wonderful: Billy’s enunciation of “hexavalent chromium”
Standout Moment: Like a beautifully hand-drawn illustration with layers of meaning and comprehension, so too are “Billy on the Street” obstacle courses. Yes, there are the jokes you see coming 1.2 seconds before they happen, like the one that arrives shortly after the mere mention of “Valentine’s Day.” But then come the tiny, tossed-off moments, like Dratch plaintively explaining “I drew a heart…” or a breathless Billy gasping out a quick “Hi, Richard Gere!” at a waving cardboard cutout. “Mechanical Bullock,” “Name Twenty White People” and “Escape from Scientology” are similar, sumptuous tapestries, but this Julia Robstacle Course is the standard-bearer.

For a Dollar!

Season: 3
What Made It Wonderful: “Radio Shack.”
Standout Moment: a murderer’s row of people slowly realizing what’s happening to them. Yes, it’s a hallmark of the show, but this edition of “For a Dollar” is a glorious cross-section of how “Billy on the Street” has genetically engineered this format to confound its “contestants.” New York is this show’s grand experiment, testing the limits of people’s willingness to agree with gossip column proclamations and celebrity hot takes. The great thing is that no one quite seems to realize they’re part of the Petri dish until the camera moves on.

Denzel Washington!

Season: 3
What Made It Wonderful: everyone shouting “JOHN Q! IT’S JOHN Q! THE NAME OF THE MOVIE IS JOHN Q!” at their screens
Standout Moment: Indignation is the fuel to Billy’s fire, but few moments in the show have ever drawn out quite this level of stunned disbelief. It’s a wonder that Billy’s larynx lived to tell the tale. (Bonus points for somehow name-dropping not one, but two 2016 awards season contenders four years in advance.)

Amy Poehler in Masks!

Season: 3
What Made It Wonderful: Poehler’s face at the mention of “Free Birds”
Standout Moment: “Billy on the Street” often lives on the thin edge between wonder and terror. With one notable exception, every person in this montage seems legitimately frightened by this very rapid succession of reveals. As worldwide recording star Pitbull gives way to Leslie Knope, the reaction shots are like something out of the night-vision footage they use to sell “Paranormal Activity” sequels. These are New Yorkers who are used to seeing many things walking between subway stops, so it’s always delightful to see them genuinely taken aback by something truly unbelievable.

FLOTUS and Big Bird!

Season: Web Exclusive
What Made It Wonderful: Gwyneth Paltrow (no really)
Standout Moment: Not the most representative installment, given the empty grocery store setting, but when First Lady Michelle Obama and Sesame Street’s large, lovable canary teamed for a special nutrition-themed segment for Funny or Die, it still managed to bring some of the show’s standbys. Best of all? The small but noticeable double-take when fan-favorite Elena finds out who she’ll be competing with.

Tina Fey!

Season: 4
What Made It Wonderful: The Collapse
Standout Moment: Whenever “Billy on the Street” turns its laser-like, on-the-spot focus back on its celebrity guests, the results are often spectacular. The panicked look in Tina Fey’s eyes as she realizes what’s about to transpire is as genuine as any unsuspecting person being asked about Dakota Fanning’s diet regimen at a crosswalk. Part “Celebrities! They’re just like us!,” part sly commentary on the need for greater diverse representation in Hollywood, it’s a tribute to what the show can uncover when it fully commits to the promise of its premise.

Shondaland!

Season: 4
What Made It Wonderful: the actress who remains deathly still even while being grinded on
Standout Moment: Amy Sedaris’ run through a Shonda Rhimes-themed obstacle course is the greatest thing she’s done this side of Princess Carolyn. Watching her burst through a (sugar-)glass ceiling, berated by Billy like an overbearing camp counselor, is delightful. Billy’s street-side improvisation gets it’s well-deserved due, but “Billy on the Street” is also a prime showcase for magic built on great planning and execution. Case in point: “The Olivia Pope-mobile” on its own is a genius idea, but the reveal of the design/operation of said vehicle is what puts this one over the top.

Thanksgiving!

Season: 4
What Made It Wonderful: imagining a world where “Carol” is celebrated every holiday season
Standout Moment: Neck and neck with the “Portlandia” “Allergy Pride Parade” for the decade’s best parade spoof sketch, Billy grabbed some time behind a desk for a reimagining of the yearly Macy’s celebration, filling the caravan with some impressively detailed floats and balloons. (There’s inside baseball and then there’s a fleet of publicists waving banners with the names of real-life PR firms.) Somehow, the assembled list of celebrities work both as comical sixty-foot versions of themselves and the ideal names for faux-cheery comic emphasis, delivered by Billy and (of course) perpetual good sport Katie Couric.

Julianne Moore Crying!

Season: 4
What Made It Wonderful: Billy’s exhaustive knowledge of Oscar history; the woman in the glasses at the 2:05 mark who is severely perplexed by this development
Standout Moment: Julianne Moore doing the acting equivalent of busking for New Yorkers is a joy. Watching her summon the fiery outrage, defeated sadness and quivering lower lip of great performances past is truly a thing to behold. But then pops up that wonderful, bright-blue-backpacked woman (again, skip to 2:05 in) who clearly cannot process that this is happening. She only lingers for a few seconds, but few performances have been able to capture the raw bewilderment that must have surged through her as she walked past Academy-Award winner Julianne Moore yell “Shame on you!” at unassuming passersby. Never change, New York.

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