The 12 Best Billy On The Street Moments Ranked

Comedian and actor Billy Eichner recently made history with the movie "Bros," which is the first big studio rom-com to feature an openly gay lead actor. The movie is also comprised of a principal cast of LGBTQ+ performers such as Ts Madison, Guillermo Diaz, Amanda Bearse, and Luke Mcfarlane. Despite the disappointing numbers at the box office, "Bros" has received high praise from critics and audiences alike.

Long-time Eichner fans will remember how he got his start with the hilarious series "Billy on the Street." The show premiered in 2011 on the Fuse network, continuing for three seasons until it was picked up by truTV in 2015. Eichner has also made several stand-alone episodes for YouTube.

The initial premise of the Funny or Die series was "a music and pop culture game show," but most fans know it as an opportunity for the host to shove a microphone in the faces of New Yorkers and scream his opinions at them. Of course, that's all just part of the fun. Games like "For a Dollar" and "Quizzed in the Face" made up most of the first season, with new content and more celebrity guests appearing in later seasons. Still, of all the fantastic, laugh-out-loud moments in "Billy on the Street," which ones stand out above the rest? Here is our top 12 list of the best "Billy on the Street" moments ranked.

Throughout the series, Eichner has made it clear that he is a huge stan of Oscar-winning actor Meryl Streep. In this Season 3 segment, the host gathered a compendium of young women dressed as iconic Streep characters and tested their knowledge of trivia in an exhaustive relay race and obstacle course – all centered around Streep's film career.

With the five contestants dressed as various characters from Steep's movies, each takes their turn running down the sidewalk while being bombarded by questions from Eichner. The group then has to run through a complicated obstacle course made up of famous Streep films, including "Sophie's Choice," "Julie & Julia," and "The Devil Wears Prada." Finally, the contestants and Eichner finish the course on the Meryl-Go-Round –- a spinning carnival ride that straps everyone in while the host frantically finishes the last round of questions.

We can honestly say that we've never quite seen a game show like this, as a Julia Child look-a-like shoves chicken into a cardboard cut out of Stanley Tucci and Margaret Thatcher is forced to lie down in a casket. Yet this is why we love "Billy on the Street" -– it's content you won't find anywhere else.

Times Square is a famous hotspot in New York City and is known for attracting tourists. This is why it is the perfect spot for costumed performers to gather and offer photos for tips. In one "Billy on the Street" Season 4 episode, Eichner and special guest Julianne Moore decide to take advantage of the bustle in downtown Manhattan for their own purposes.

Taking monologues from some of her famous award-nominated roles, Moore performs for various people on the streets for a small gratuity. As she recreates an emotionally-charged scene from "Magnolia," one onlooker in the background can be seen giving bewildered looks to the red-haired actor. When another confused tourist confesses that he doesn't know who Moore is, she gives an Oscar-worthy performance by crying on cue. Eichner then insists that the young man give Moore a hug to "comfort her in her time of need."

When Eichner shoves a Spider-Man impersonator out of the way to showcase Moore's talent, the gathered pedestrians quickly forget about the comic book hero. One fan in the crowd points out that the web-slinger doesn't have an Academy Award, to which Billy responds by having everyone look into the camera and say, "F*** Spider-Man!" Okay, that might be a little harsh, but it's not every day that a legendary actor graces Times Square to perform for tips.

The famous "Billy on the Street" Lighting Round, colloquially referred to as "For a Dollar," has Eichner approaching random people and awarding them one dollar if they correctly answer a question. The catch is that most questions are based entirely on Eichner's personal opinions, and he often has some controversial ideas. During one Season 4 Lightning Round segment, Eichner is backed by a small gospel choir that celebrates right answers with a lively tune and mourns wrong ones with a sorrowful lament.

With the enthusiastic gospel singers in tow, Eichner approaches random pedestrians with questions like "Who is more of a hero; Nelson Mandela or Elizabeth Banks?" and "Which would make you happier; winning the lotto or John Cusack playing one of The Beach Boys?" With every right answer, Eichner and the choir respond with a joyful refrain of a gospel classic. Eichner also throws some of his own improvised lyrics into the mix. This segment not only makes for some comedy gold but also has us clapping along and tapping our toes. 

On occasion, Billy Eichner has had some confrontational encounters with strangers while filming "Billy on the Street." At times this is due to the bombastic persona that Eichner adopts for the show. Yet in one Lightning Round segment, the host's memorable argument with one New Yorker was possibly justified.

In this clip, Eichner asks a woman her thoughts about movie star Denzel Washington. Though she claims to be a fan, she can't quite remember the name of her favorite Washington movie as she describes the plot for the 2002 thriller, "John Q." Things quickly take a different turn when an argument erupts as the woman insists that Washington played the Phantom in a production of the Andrew Lloyd Webber musical, "The Phantom of the Opera." Even when Eichner walks away in a huff, the woman follows, insistent on continuing the debate.

The discussion turns into a hilarious shouting match between Eichner and the woman, who refuses to back down on her statement. We're not sure which is funnier -– the fact that Billy continues to interact with her or that she is so relentless in her conviction, even though it's wrong.

Before "Bros," there was the Bro Lightning Round on "Billy on the Street." Backed up by a hype group of masculine men, including "Ted Lasso" star Jason Sudeikis, Billy put on his best bro accent and played "For a Dollar" with unsuspecting pedestrians.

Wearing jerseys and ball caps, Eichner and his frat boy entourage asked questions of random New Yorkers such as "True or false: masculinity is a prison," "Which is better; 'Aladdin' or 'Wicked'?" and "We good?" They conclude with a "Wicked" tailgate party, complete with green face paint, a frisbee with Idina Menzel's photo, and a truck with a green sign that reads: "Bros before shows." Amidst high-fives and chest bumps, we're also treated to a view of Eichner doing a keg stand with a photo of musical composer Stephen Schwartz plastered on the front of the keg.

The segment is a funny satire of "bro" culture and toxic masculinity, albeit with a clever twist. After all, just because you like sports and chugging beer with your fellow bros doesn't mean you don't like to take in a classic Broadway musical once in a while. Menzel for life, bro! 

Actor, comedian, and acclaimed host of the HBO late-night talk show "Last Week Tonight," England native John Oliver has made a pretty big name for himself in the States. However, it seems that some people out there still have never heard of the Emmy-award-winning performer -– many of whom appear to be a part of the New York LGBTQ+ community.

In 2017, Oliver appeared as a guest in an episode of "Billy on the Street," in which he and Eichner played a special game titled "Do gay people care about John Oliver?" Though this hilarious segment didn't do much for Oliver's ego, it did plenty for our funny bones. As Eichner puts the question to gay men off the street, some don't even realize who John Oliver is -– or that he is standing right in front of them.

In contrast, many seem to really like media personality Wendy Williams of "The Wendy Williams Show." When one person enthusiastically answers in the affirmative in regards to Oliver, Eichner then follows up by asking whom they like better — John Oliver or Wendy Williams? The young man sheepishly answers Williams, to which Eichner responds with, "I knew it!" Now that more than five years have passed, hopefully more folks have begun to care about John Oliver.

One of the best things to come out of "Billy on the Street" is the unlikely friendship between Billy Eichner and Elena. Eichner's love for the queen of sass is so strong that he even brought her as his date to the "Bros" red carpet premiere, as he shared on Twitter. There was also a special edition of "Billy on the Street" in which Elena helped to promote Eichner's movie, "Bros." Elena's deadpan expression and sardonic energy complement Billy's manic sarcasm perfectly, and we love her for it.

It's difficult to pin down the best Elena moment of all the incredible moments she has in "Billy on the Street." Yet there's nothing quite like her very first appearance in the first episode of Season 2. Singled out by Eichner to play a game of "Quizzed in the Face," Elena looks anything but thrilled by the prospect of earning easy cash. However, thanks to a bit of convincing by Eichner, she ends up roped into the trivia game despite her reluctance.

Not only does Elena dish out as much as Billy gives, but she also answers every question right. While she continuously checks her watch in a hurry to meet a friend, she sticks it out all the way to the end, albeit intermittently rolling her eyes and emitting heavy sighs. With many more beautiful Elena moments to come, the meet-cute of this platonic love story is truly one of the greatest "Billy on the Street" moments.

In one Season 5 episode of "Billy on the Street," Eichner played a rather dark prank on random passersby in New York City. In a segment called "Death Rogen," special guest star, Seth Rogen, pretends to be one of the show's camera operators. With Rogen's face hidden by the camera, Eichner approaches various strangers to inform them that funnyman actor Seth Rogen has died.

It's not often that one can know what people might say about you once you're dead, but in this case, Rogen gets a front-row seat. The reactions from New Yorkers upon hearing the news were mixed. Some were very sad to hear that Rogen had "passed away," saying that he was "very funny." Others admitted that they had never heard of Rogen but were sorry to hear that he had died. 

A hilariously awkward moment happens when a woman states her preference for Billy Eichner's comedy over Seth Rogen's movies before Rogen gives a sheepish wave from behind the camera. Of course, when Rogen revealed himself to be very much alive, the victims of the prank were elated and laughed at their own expense.

In this Season 5 segment, Eichner is joined by "Mad Men" star Jon Hamm. Eichner claims that in an effort to keep up with progressive film and television trends, "Billy on the Street" is going to ask the people of New York a very important question: Who wants to have a threesome with Billy and Jon Hamm?

In this spin on "For a Dollar," Eichner and Hamm proposition people of varying genders and sexualities. Two married women, though they need some convincing, are on board with the idea. One young man agrees as well, although he causes a bit of a stir while discussing the details of everyone's roles in the scenario. Another man also answers yes, but Eichner warns him that Hamm might want to try out some of his comedy personas during the act. In another instance, one woman says she would agree to go to bed with Hamm but not with Billy because she doesn't know who he is.

Whatever their preference, it seemed like most of those surveyed were more than happy to join in a ménage à trois with the acting star and comedian. They never follow through, of course, but it's good to know that New Yorkers seem to be so open-minded.

The "Billy on the Street" Lightning Round is one of the most recognized segments in the series. Running down the busy city streets with a microphone in tow, Eichner pounces on unsuspecting strangers to ask them questions. Sometimes he doesn't even get a question in but instead shouts the name of a celebrity at them to gauge their reaction. Some of the show's funniest moments involve the host startling a person by shoving a microphone in their face, only to have them yelp in surprise or run away.

One clip from Season 2 has Eichner cornering people to ask them seemingly simple questions. However, when they are suddenly put on the spot, they find it difficult to give a satisfactory answer. The first person Eichner approaches is asked to name three white people but accidentally answers Michael Jackson. When Eichner asks a young woman carrying a yoga bag to "name a woman," she is stumped. She repeats the question, only to find that her mind has suddenly gone blank. By the end, Eichner is shouting at her to "Name a woman," only to scare her off as she runs away. 

In their defense, if a stranger with a microphone suddenly came up to us and asked us a bizarre question, we would probably be flabbergasted and tongue-tied, too.

Star of "Ant-Man" and Judd Apatow comedies like "This Is 40," actor Paul Rudd is famous for his seemingly never-aging features. When Rudd appeared as a guest star in Season 3 of "Billy on the Street," he and Eichner took to the streets to play a very special Lightning Round, in which Eichner posed the question the random strangers: "Would you have sex with Paul Rudd?"

Rudd seems perfectly happy to participate, keeping pace with Eichner as they rush down the street. Stopping several pedestrians, Eichner asks people of various genders and ages if they would like to have sex with Rudd. It should come as no surprise to anyone that the majority of folks reply in the affirmative — though some were perhaps more enthusiastic than others. Rudd graciously smiles and thanks those who give positive answers, occasionally stopping to give hugs until Eichner stops that madness. 

Eichner also couldn't resist making a jab at the actor for his role in the 2010 comedy flop, "Dinner for Schmucks," citing the movie as the reason why one person turned down Rudd's offer.

It should be no surprise to see this iconic "Billy on the Street" moment at the number one spot on the list. Even those who haven't seen the show should recognize the host of memes it inspired.

In this segment from Season 2, Eichner films a special edition Lesbian Lightning Round, in which he and five lesbians survey random people about their personal taste in celebrities. Eichner asks several men and women to choose between Kesha and Britney Spears, then Britney Spears and Christina Aguilera, and others. He then poses the same question to the entourage of women, seeming to go with the popular vote. Yet it's the moments in between that are the real gem of the piece, as Eichner leads the "pack of wild lesbians" on a speedy chase while chanting, "Let's go, lesbians, let's go!"

The Lesbian Lightning Round was such an internet hit that "Billy on the Street" brought it back in a later episode. In 2019, actor Chris Evans guest starred on the show to promote the movie "Knives Out." Evans and Eichner were soon joined by Paul Rudd, whom they ran into seemingly by surprise. The tail end of the clip brings yet another familiar favorite, as Eichner and Evans are joined by another group of lesbian women. After uttering his iconic phrase — "Let's go, lesbians!" — Eichner and Evans go running down the street joined by their own personal Avengers. Lesbians, assemble!