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Top 10 Funniest Billy on the Street Moments

VO: Rebecca Brayton WRITTEN BY: Nick Miller
He takes “man on the street” to a whole new level. From hangin’ with Amy Poehler (or should we say Pitbull?), to harassing New Yorkers with Neil Patrick Harris, to the difficult task of NAMING A WOMAN!!, these videos are side splittingly funny. WatchMojo counts down the Top 10 Funniest Billy on the Street Moments.
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Script written by Nick Miller

Top 10 Funniest Billy on the Street Moments


He takes “man on the street” to a whole new level. Welcome to WatchMojo.com, and today, we’re counting down the top 10 funniest “Billy on the Street” moments.

For this list, we’re looking at the best moments from Billy’s TV series and online shorts, or from any of the series’ web specials.

#10: It’s Not Pitbull; It’s Amy Poehler! (2014)

The key to the success of a “Billy on the Street” bit is landing a genuinely funny reaction from strangers, and when Billy brings out comedian Amy Poehler wearing a mask of Florida rapper Pitbull, there’s no shortage of hilarious receptions, from a screaming fanboy to a man who may or may not even recognize the “Parks and Recreation” star, and is apparently “not familiar” with the series. Putting Poehler in a Pitbull mask is just the right kind of weird to be utterly hilarious when she unmasks, because really, who in the world would expect a “Saturday Night Live” alum to be running around the streets of New York in a Pitbull mask?

#9: Billy & Neil Patrick Harris Ambush New Yorkers (2014)

When it was announced that “How I Met Your Mother” would be coming to an end back in 2014, it seems Billy took it extremely hard. In this gut-busting segment, Billy and show star Neil Patrick Harris ask New Yorkers their thoughts on the series ending, with responses ranging from sheer disappointment to one man’s guttural happiness at the prospect. Billy is especially worried about Cobie Smulders’ next career move, and thankfully it seems the people of New York are equally as concerned. Or maybe they just don’t know who she is. Like many of the show’s best segments, the rapid fire editing keeps us laughing through the entire clip.

#8: Name a Woman!! (2013)

Have you ever found yourself caught off-guard and unable to answer a simple question? You might relate to this young lady, who finds herself unable to name a single woman after Billy surprises her with the simple request. As the seconds tick by, Billy quickly gets increasingly frustrated as the young yoga mat-carrying woman is thrown by the easy question and gets flustered, waving his microphone in her face and screaming until she is finally scared off. The entire exchange lasts less than 30 seconds, but Eichner’s response to this off-the-cuff moment is pure comedic gold.

#7: Mr. Singh Gets Quizzed in the Face (2013)

Alongside fellow Quizzed in the Face contestant Elena, Mr. Singh is one of the most memorable non-celebrities featured on the series since it debuted. Though he starts off pretty calm, Mr. Singh eventually starts to let loose, throwing shade at the likes of Lindsay Lohan and even Billy himself. One of the few New Yorkers that Billy doesn’t scream at, Mr. Singh is an absolute treat of a contestant, doing his best to guess his way through some difficult pop culture questions. Unfortunately, he lost, but in the eternal words of Mr. Singh, “sooner or later, we’re all out of the game.”

#6: Talking Food & Pop Culture with Big Bird, Michelle Obama & Elena (2015)

In a special non-New York web episode of the series, Billy talks to First Lady Michelle Obama along with “Sesame Street’s” Big Bird and special surprise guest Elena, asking them a series of ridiculous questions about celebrities and healthy eating. If you’ve ever wondered what Elena’s thoughts are on One Direction, or felt the urge to see Michelle Obama slow dance with Big Bird to the dulcet tones of Billy Eichner, this segment is for you. Big Bird is surprisingly quiet during the episode, but his Jim Halpert-esque camera glances are worth a thousand words.

#5: Would You Have Sex with Paul Rudd? (2014)

When the handsome and charming Paul Rudd appeared on Billy’s show, Eichner dragged the comedian through the streets, asking strangers if they would have sex with the “Ant-Man” star for a dollar. As you might expect, there are a lot of positive responses, with a few negative, but, as usual, it’s Eichner’s over-the-top reactions that keep the comedy ball rolling. More recently, the host brought this game back with an update, asking passerbys if they would have a threesome with himself and professional handsome actor Jon Hamm, but it’s the original game that truly had us in stitches.

#4: Julianne Moore Acts Out (2015)

When acclaimed actress Julianne Moore appeared with Billy, the funnyman had the wonderful idea of Julianne acting for tips in Times Square, just like the costumed cartoon characters that take photos with tourists. The result is utterly side-splitting, with the Academy Award-winning actress performing lines from a variety of her dramatic movie roles for strangers on the street. The best part of the entire segment is that Moore gives a number of surprisingly good performances despite the absolutely ridiculous situation, with the reactions of other folks on the street ranging from amusement to absolute confusion.

#3: DEATH ROGEN! (2016)

The closest thing on our list to a prank came when Billy invited comedian Seth Rogen onto the show. Eichner had Rogen act as a cameraman, filming the reactions of New Yorkers when Billy breaks the news that Seth Rogen has passed away. As with many “Billy on the Street” celebrity segments, some of the funniest moments come from someone not knowing who the famous person is, and others come from when people find out that not only is Seth alive, but he’s standing right in front of them. The segment culminates with Billy swearing up and down that he isn’t lying to a woman before revealing the truth, giving way to her priceless reaction.

#2: Billy Gets into a Fight About Denzel Washington (2013)

When Billy asks a woman her thoughts on Denzel Washington, the conversation soon devolves into an argument as to whether or not the Oscar-winning actor ever played the Phantom of the Opera on Broadway. The woman is quite adamant, and Billy is as boisterous as ever. As the argument escalates, the pair are forced to move down the street and their conflict continues, with the woman citing the memory of her daughter’s birth as proof of Denzel’s Broadway role. It’s an absurd moment that perfectly captures what “Billy on the Street” is all about: combining Eichner’s larger-than-life personality with that of some of New York’s most funny and eccentric residents.

Before we reveal our top pick, here are a few honorable mentions.
- “La La Land” or Nicki Minaj? (2017)
- Billy Hits the Streets with Emma Stone (2018)
- Christmas with Will Ferrell! (2015)

#1: Do Gay People Care About John Oliver? (2017)

When Billy had HBO comedy news host John Oliver on the show, the pair set out to answer the age-old question: Do gay people care about John Oliver? The answer? Apparently not a whole lot. Billy and John ventured out to the street of NYC, asking the question without any context. The majority of the time, the gay men asked seem pretty disinterested in the “Last Week Tonight” host. Oliver’s reaction to the segment is bemused acceptance, even when the few gay men who do care about John Oliver still seem to appreciate Wendy Williams more.

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