Photo-Illustration: Vulture and Photo by Universal Pictures

This article originally ran in 2016; we’ve republished it in honor of the tenth anniversary of The Lonely Island’s Incredibad.

Over their 15-year career, the comedy trio the Lonely Island has won an Emmy and a Peabody, earned three Grammy nominations, and released two top-ten albums and two platinum singles, and their videos have been seen more than 1.7 billion times on YouTube — and it’s all been building toward a flaccid penis.

Midway through Akiva Schaffer, Andy Samberg, and Jorma Taccone’s film Popstar: Never Stop Never Stopping, Samberg’s character, a Justin Bieber and Macklemore hybrid named Conner4Real, begins waxing faux humble about the boobs one fan pressed against his limo window and how they’re the reason he does what he does, when, suddenly, a hanging limp member appears. Conner, oblivious, brags that he’s going to sign what’s behind him, rolls down the window — you see where this is going.

Outrageous and destined to be iconic, the scene shows the Lonely Island at the height of their powers: This penis joke uses the vocabulary of modern pop stardom and the rhythms of online comedy to undermine male insecurity. As such, it’s pretty much the epitome of what Samberg, Schaffer, and Taccone have been doing since they started making comedy. Or, as they once said about their wildly and improbably successful career, there are two rules: music and dick.

As you’ll see, those rules have served them well.

1. Cut a hole in a box.

The Lonely Island disrupted the distribution and aesthetic of filmed comedy.

Related Stories Picking The Best Lonely Island Short of All Time

Comedy is all about timing. YouTube officially launched on December 15, 2005. The Lonely Island premiered their second SNL digital short, “Lazy Sunday,” two days later. The site and the group have been irrevocably linked ever since. Milton Berle earned the nickname “Mr. Television” for figuring out how comedy worked best on television. The Lonely Island occupy a similar position vis-à-vis the internet — there were others doing comedy online prior, but this trio made it work for a mass audience.

It’s important to understand how out of place the Lonely Island were, coming from making videos for the web, when they got hired on SNL. After the show’s divisive experiment with a stand-up-heavy cast in the early ’90s, Lorne Michaels & Co. shifted back to the sort of improv-trained cast that defined the show’s earlier peaks. By 2005, the cast featured an incredible 11 cast members who had improv backgrounds. One of the few exceptions: Andy Samberg, who years earlier had suffered through a disastrous Groundlings audition. He told Pete Holmes about it, on his You Made It Weird podcast, saying that failure had made him realize his true métier was video.

Samberg, Schaffer, and Taccone’s path to SNL seems reasonable now, in an environment that rewards independently minded grinders, but that path — from the margins to the mainstream — was forged by these three. In 2000, after graduating from different colleges, they all moved to Los Angeles, living together in an apartment they named the Lonely Island after a faux-pretentious one-act play Schaffer wrote to make fun of Taccone. The Lonely Island would also become the name of their website, through which the gang gained their first competitive advantage: Thanks to Schaffer’s brother (who later got a job at YouTube), the site featured streaming video. After five years of shooting sketches and posting them online, they had shot a sketch pilot for Fox called Awesometown that went nowhere. But that wasn’t what put them on Lorne Michaels’s radar. No, their big break came working on the 2005 MTV Movie Awards, hosted by Jimmy Fallon.

Lonely Island wrote two of the pretaped sketches — parodies of Batman Begins and Star Wars: Episode III — and Fallon loved their work (and Samberg’s impression of him) so much he called Lorne Michaels and recommended they audition for SNL. Samberg was the only one who got the gig. (Schaffer never auditioned; Michaels passed on Taccone.) SNL producers Mike Shoemaker and Steve Higgins told Michaels about the Lonely Island’s online sketches. After the boss watched some of those, he hired Taccone and Schaffer as writers on the show.

But just because you’re hired at SNL doesn’t mean you wind up on the air. In the SNL oral history Live From New York, Schaffer described their role as being “the team of ‘getting Andy on the show,’” and initially they had a terrible win-loss record. Halfway into their first season, they hit their breaking point, in the form of a failed pitch in which Samberg was to play a little boy who simply wants to wear shorts at night. But the rejection made them think that live sketches were not the best medium for their ideas. “We started to realize,” Taccone explained, “that some of those weirder concepts were things that we just needed to film and present because that was the way to show people that it was potentially good.”

During an SNL off-week, they borrowed a camera from Bill Hader’s wife, director Maggie Carey, and shot a Ying Yang Twins parody, “The Bing Bong Brothers,” starring Taccone and Schaffer. They played it for Michaels, who then said he’d be open to the prerecorded videos on the show as long as they included cast members. So, on December 3, 2005, employing the Digital Short rubric Adam McKay had used a few times previously, SNL premiered “Lettuce,” a simple surrealist sketch in which Will Forte and Samberg chomp heads of lettuce while having a serious conversation. It played well enough that they got to do another one. Schaffer credited the show’s willingness to embrace video to the fact that it was so cheap. (“Lettuce” cost $20.) “If we made a video for free on our own time and then it comes out badly, there’s no embarrassment there,” Schaffer explained. “Whereas if we asked for a big budget and did it in the system, and then it turned out stinky, maybe we’d never get another shot.”

The trio’s breakthrough, of course, was “Lazy Sunday,” a gangsta-rap ode to their lame, cupcake-filled day off, which went viral before viral was a thing. At the time, the Lonely Island had never heard of YouTube. As Schaffer recalls in Live From New York, “My brother e-mailed me and told me, ‘Look at this place where you can watch [“Lazy Sunday”] online.’” By the end of the week after it aired, “Lazy Sunday” had been viewed more than 2 million times on YouTube, an unfathomable number at the time. (YouTube’s overall traffic jumped 83 percent in the weeks to come, a fact some credit in part to the success of “Lazy Sunday.”)

It’s easy to knock the Lonely Island for just being in the right place at the right time, but to do so would be to overlook an element of the group’s sketches that made them ideal for the internet: editing.

In this regard, Schaffer, who directed the majority of the early Digital Shorts, was the Lonely Island’s secret weapon. “Akiva was always the one that made everything look way better than it cost, and edited it,” Samberg told Holmes. In addition to creating the group’s visual aesthetic, Schaffer created a tempo for online comedy: shorter and quicker. There were, of course, pretaped sketches throughout SNL’s history. But some of Albert Brooks’s shorts from the first season were more than ten minutes long, and the show’s commercial parodies tend to be paced like real commercials — Digital Shorts are different animals. A closer comparison is probably Robert Smigel’s “Saturday TV Funhouse” sketches, but even those are noticeably slower than what Schaffer was doing. Take Smigel’s “Christmastime for the Jews,” a stop-motion musical sketch that debuted the same night as “Lazy Sunday”: It’s short, pleasant, and filled with Jewish-Christmas references (bowling, Chinese food, etc.). “Lazy Sunday,” in comparison, absolutely blitzes through random touchstones (i.e. The Notebook, MapQuest, and the Hamilton–Burr duel). Or there’s something like “Andy Popping Into Frame,” a 71-second sketch where Samberg — yes — pops into frame in a variety of settings around New York. What makes this premise work is exactly when Samberg pops in. The humor is solely in the rhythm of the editing, a rhythm that quickly became the basic pulse of online comedy.

2. Put your junk in the box.

Lonely Island found endless ways to make, and satirize, dick jokes.

In 2012, on Andy Samberg’s penultimate episode of SNL, the show aired “100th Short,” a tribute to all the shorts the Lonely Island had done. How did the video suggest that Samberg, Schaffer, and Taccone wanted to celebrate? By sucking their own dicks, of course. Two-thirds of the way through the clip, Usher pops up and sings, “Hey, I’ve never been in a Digital Short, but these white boys are obsessed with their dicks.” He is not wrong.

The Lonely Island’s shorts include “Please Don’t Cut My Testicles,” “Dick in a Box,” and “Jizz in My Pants.” The most extreme example might be “We’re Back,” off of their Turtleneck & Chain album. On that song, each member goes all in on the grossness of their respective penises. Sample lyrics: “My dick looks like the fat that you cut off a steak / Smashed in like my balls went and stepped on a rake.” Samberg has explained that his approach to comedy is based on revisiting the things that made him laugh when he was a kid, i.e. dick jokes. Teenage boys love ‘em. So the Lonely Island keeps delivering ‘em. Over and over.

But there’s a method to this madness. Or at least it’s not as puerile as it might seem. The Lonely Island’s members were teenage boys who grew up in Berkeley, California, and they self-identify as feminists. “I think feminism is a word we didn’t know existed until we left Berkeley,” Schaffer has explained. “At Berkeley it was the norm. We were raised by [makes air quotes] feminists.” Taccone added, “We certainly were raised in an environment where equal rights for men and women was not even a thought.” “The feminist movement does not need three white guys to be their heroes,” Schaffer tells me, “but, yes, making fun of posturing and pretending to be cool and tough and masculine has always been our thing.” And it has always given their silliness a deeper resonance. The Lonely Island don’t just make dick jokes. They parody masculinity.

This was evident even before they got on SNL. In the music video “Just 2 Guyz,” which they shot in 2004 and included in the Awesometown pilot, Schaffer and Taccone play awkward dweebs pretending to be cool dudes. In monotone, they rap lines like, “Spinach dip / Real hot chicks / Spike the punch and take a sip.” These characters, which they’ve revisited throughout their career, are some of the group’s clearest send-ups of men trying to act out a ridiculous, idealized version of manhood.

“Dick in a Box” uses the sounds of sexualized ’90s-era R&B to make fun of the specific brand of male stupidity that thinks a penis is a gift to be given. The videos “Jizz in My Pants” and “I Just Had Sex” satirize the ineptitude and one-dimensionality of manhood. There’s also the “Shy Ronnie” sketches, in which the title character is only able to rap and talk tough when Rihanna leaves the room.

It’s out of this context, however, that the Lonely Island have gotten into trouble — not all of it undeserved. “Two Worlds Collide” was an attempt to parody straight-male discomfort with homosexuality, but at first glance it could appear that gay sex is being played for simple shock value. Same with “Andy’s Dad,” which gets its biggest laugh when Jonah Hill appears to go down on a guy. Or there’s “Everyone’s a Critic,” which aired on an SNL episode that Gawker derided as a “Gay Minstrel Show.” When addressing the latter directly in his 2009 Out profile, Samberg called it “bro-gay.” “Dudes that are bros and super antigay are the ones who need to get it the worst,” Samberg said. “They’re the ones we have the most fun fucking with.”

The Lonely Island got better at making it clear whom they were targeting. In the video for “Spring Break Anthem,” off of 2013’s The Wack Album, they contrast heternormative spring-break debauchery with beautiful images of same-sex marriage.

“A lot of our songs are making fun of being macho and for some reason, the thing that macho guys are most afraid of is homosexuality,” Schaffer said about the song. “It’s a great juxtaposition in general of machoness in pop and rap — that’s why we go there. Our intention is not gay focused; the joke is always on being homophobic.” Taccone added, “We’ve known each other since junior high school, and one of our favorite jokes is to make homophobic people uncomfortable.”

3. Make her open the box.

The Lonely Island made their weird accessible.

In his 2014 WTF interview with Marc Maron, Samberg explained the two types of SNL sketches: the “weirder stuff” that airs late in the episode and the “big flashy, Miley Cyrus twerking, pop-culture thing at the top of the show.” The Lonely Island’s trick is to use the pop-culture thing to sneak in the weirder thing.

Before SNL, the Lonely Island first made a name for themselves with the Channel 101 O.C. spoof, “The ‘Bu.” The first episode begins with an animated squirrel telling the audience that some of the episode will be in 3-D and that he’ll let everyone know when it’s time to put on their glasses. What follows is a melodramatic scene between two young people that gets interrupted every few seconds by the squirrel yelling “glasses on” and “glasses off.” Eventually, the whole thing breaks down into full absurdity. Yet, because this was taking place inside a parodic framework, it all somehow seemed more reasonable, more grounded.

After arriving at SNL, the Lonely Island kept using both pop culture and parody as a Trojan Horse for their weirdness. Take “The Shooting,” in which the Lonely Island once again used The O.C., referencing Marissa’s shooting of Trey. The sketch takes the beat used by the teen soap, where everything goes slo-mo to the sound of Imogen Heap, and repeats it again and again and again and again. It is so, so funny, but it’s also the sort of extreme use of repetition that can turn people off (see: the sketch Samberg did in “Second Chance Theatre” earlier this month). But again, within the conceptual structure of a parody, it works.

As far as utilizing pop culture, the Lonely Island would’ve never become the Lonely Island without “fake rap.” Despite performing comedy raps in junior high for fun, Schaffer, Samberg, and Taccone were hesitant about doing the same on SNL. “We always were also slightly embarrassed by it,” Schaffer explained. “We considered musical comedy kind of a crutch, and fake rap specifically as a lame thing to do.” There’s also the obvious racial dicey-ness. “We all agree raps for comedy, if you’re a white person, is a very slippery slope,” Samberg told Maron. “It’s not really your place.”

But SNL’s demand for material — and competition for camera time — made the guys desperate. “The reason we’ve gone so heavy into [musical comedy] has been about the audience response,” says Schaffer. “Not like the other stuff was bad or anything, but those were the ones people wanted to watch again.”

Still, they felt they needed to develop a set of criteria that they felt made it okay. As Samberg put it to Maron, the goal was to “(a) make it sound legit” and “(b) have a genuine knowledge of that world and respect for it.” As Taccone told The Guardian: “We’re using it as a medium to tell a joke, not making fun of music necessarily.” Simply, the Lonely Island are not doing piss-take rap — rap where the joke is that the music is intentionally bad. Or as Schaffer puts it to me, “I would challenge anyone to think that any of our songs wouldn’t also be funny if black people were singing them.”

The Lonely Island are less parody artists like Spinal Tap or Weird Al and more like ’50s and ’60s comedian Tom Lehrer, who used music to make jokes about disparate subjects. “Diaper Money” uses rap to mock the fear of growing up. “Jack Sparrow” contrasts the Lonely Island’s raps about clubbing with a non sequitur chorus that features Michael Bolton singing about his love of the Pirates of the Caribbean movies. That very catchy, weird-as-hell song has 150 million YouTube views.

The group’s success with this stuff isn’t actually all that surprising. People listen to music without understanding — or even caring about — the lyrics all the time. The Lonely Island, who’ve been using professional producers since 2009’s Incredibad, have been able to make music that’s good enough to be popular as music, and among people who don’t typically listen to musical comedy.

And that’s the way you do it

The Lonely Island’s double-edged legacy.

Samberg, Shaffer, and Taccone have always been determined to make their jokes amount to more than the fact that they’re three white guys making rap. Others haven’t. Online comedian Jon Lajoie, for instance, got tens of million of views for songs that hit only that note. More recently, rapper-comedian Lil Dicky, who started rapping because it was easier than writing a screenplay, has been successful mining one gag: He is white and rapping. Lajoie’s and Dicky’s achievements likely reveal something that has always been clear to those who’ve followed the Lonely Island’s career: Some of the people who like the group probably don’t get the joke. These are the people who unironically scream, “I’m on a boat,” when, indeed, they are on a boat, or who reflexively laugh at the sight of men kissing, not knowing that their gay panic is actually the target of the joke. It’s a problem.

It’s a problem that they address — well — with Popstar. By having Samberg explicitly play a fully fledged character and not some version of himself, it’s more apparent that the joke is on a stupid pop star who’s trying to rap. “Creating a world where we’re able to say that ‘this guy’s album is tanking because it’s bad,’” Schaffer tells me, helps underline the humor. “[It’s] useful for whatever percentage of the audience doesn’t get what we’re doing.” Along those lines, the movie features a song like “Equal Rights,” in which Conner can’t stop interrupting his advocacy for same-sex marriage to say, “I’m not gay.” The joke is clearly on him (and Macklemore).

Popstar is arguably the best thing the Lonely Island have ever made, and it’s also arguably the most Lonely Island–y thing they’ve ever made, too. Blazingly quick, it runs under 90 minutes, but it feels like it has the sheer volume of bits that would fit in a movie twice as long. The character of Conner allows for so much. His reality is so fantastical that it means anything is possible — whether it’s Will Forte playing bagpipes at a turtle funeral or Seal’s singing enraging a pack of wolves to the point that they attack the press. And because Conner is developmentally still a child, the film is able to use his immaturity to make fun of male immaturity in general. All of the Lonely Island hallmarks are there: the editing, the parody of masculinity, the use of pop culture.

The Lonely Island’s place in comedy history is secure. Their shorts gave SNL, as Seth Meyers explained in Live From New York, a “shot of adrenaline.” They altered the perception of the show, turning Saturday Night Live into “Sunday Morning Online.” And they fostered a generation of online-comedy fans eager to share what they’d seen. Jimmy Fallon and his late-night peers — who also picked up on the viral value of a celebrity cameo — are playing in the Lonely Island’s sandbox.

You also see the Lonely Island in the cinematic quality of Key and Peele’s sketches, and their ability to operate within the visual and tonal vocabulary of their parody subjects. You see the Lonely Island’s absurdist take on popular culture in Kroll Show. You can even see a little of the Lonely Island in Inside Amy Schumer’s attack on gender norms. But mostly you see the Lonely Island in the thousands of people making comedy on YouTube, Vine, Snapchat, and Facebook, hoping to ride an independent viral hit to Hollywood stardom. And, of course, you see everything that makes the Lonely Island matter in Popstar’s flaccid penis, pressed hard against a limousine window.

*A version of this article appears in the May 30, 2016 issue of New York Magazine.