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The Lonely Island on Popstar, how to make a viral video, and the worst sex metaphor in the world

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Akiva Schaffer, Jorma Taccone, and Andy Samberg (a.k.a. "The Lonely Island") got style.
Christopher Polk/Getty Images

If you're watching a comedy music video that has you laughing and shielding your computer screen from your co-workers, there's a very good chance it's the work of the Lonely Island.

The trio — made up of Andy Samberg, Akiva Schaffer, and Jorma Taccone — is best known for the incredibly popular "digital shorts" they wrote and performed for Saturday Night Live. Songs like 2005's "Lazy Sunday" (a cocky ode to relaxing on the weekends) and 2006's "Dick in a Box" (exactly what it sounds like, featuring Justin Timberlake) became an SNL staple, and have racked up millions of hits online.

But with Popstar — the group's second feature film, after 2007's Hot Rod — the Lonely Island parlay their knack for creating punchy music videos into a truly weird and very funny pop mockumentary. (They wrote the script together, with Taccone and Schaffer co-directing.)

Samberg stars as "Conner4Real," a Justin Bieber–adjacent pop sensation whose very public meltdown becomes a national fixation. Along the way, we meet Conner's childhood best friends and former boy bandmates (Taccone and Schaffer), his enabling entourage, and a whole mess of celebrities tapping in as themselves, from Seal to A$AP Rocky to Mariah Carey, the elusive chanteuse herself. The movie is enthusiastically silly and, as Conner grapples with fame, even a little touching.

I spoke with Samberg, Taccone, and Schaffer on the phone this week to talk about Popstar, what it takes to be famous in 2016, and whether the Mona Lisa is really all that great. The interview has been lightly edited for length and clarity.

Caroline Framke: So how long has this movie been in the works, and what made Popstar the next thing you wanted to do together?

Andy Samberg: We were wanting to make a movie that we could write comedy music for for a while. We were debating a few different ideas, and one of them was the idea of making our version of a pop documentary, because we liked the big, bright feel of them, in terms of the comedy. And Akiva had a meeting with Judd Apatow, who had the exact same idea.

Caroline Framke: One thing I really liked about Popstar — and that strikes me as deceptively hard to pull of — is that it includes a lot of smart songs that are supposed to be actively terrible in the reality of the movie. How do you approach writing bad songs while still being funny?

Akiva Schaffer: It's actually kind of freeing to have the context of [Conner4Real's] album doing badly and that people don't like the songs, because it kind of frees you up to do the silliest songs you can think of. And they don't have to be "bad," they just have to be … ill-advised. You know, "I'm so humble being so braggy about being humble," or any of the other ones with their various offensive or ridiculous premises.

Caroline Framke: Being in a packed theater for "fuck me like Bin Laden" was definitely one of the better theater experiences I've had in a while. How did that one come about?

Jorma Taccone: We were just thinking of over-the-top R&B sex songs, and there are so many different ones. Like, "You remind me of my Jeep." Just tortured sex metaphors.

Andy Samberg: Yeah, it was like, "What's the worst metaphor we could think of?" Turns out, that was it.

Akiva Schaffer: We found it! We found the worst one! Objectively, that's the worst.

Caroline Framke: The visual of Conner performing the song with a woman in a bin Laden costume definitely brought it to another level. How did you create Conner's tour, with all its ridiculous background gags?

Jorma Taccone: We just watched a ton of documentaries that all obviously had a ton of tour footage. We know what it takes to put on a live stage show from some of the live performances we've done, like the Emmys or the Oscars. So we knew we obviously wanted to have huge dance numbers, choreography, the band onstage, the screens … there's a ton that goes into a huge tour like that.

We knew we wanted it to look massive in the way that, like, Beyoncé has huge screens, and a ton of stuff going on. There was a lot of planning in that, to make sure it looked as real as possible, while [still] being ridiculous.

Caroline Framke: Your background dancers at the very least accomplished that.

Jorma Taccone: Yeah, there's some really funny costume stuff that breezes by, so maybe on a second viewing you'd notice even more, like all of the dancers dressed as Mona Lisa in picture frames. There's a lot of ridiculous detail in the background.

Caroline Framke: The Mona Lisa song [in which Conner calls Leonardo da Vinci's painting an overrated Garbage Pail Kid] is really unexpected and fun.

Andy Samberg: We've been shocked at how many people tell us they genuinely connect to that song. "I actually went to the Louvre and was like, 'Yeah, that sucks!'" And it's like, no! That's a work of art that changed the history of art!

Caroline Framke: Or it's a Garbage Pail Kid.

Andy Samberg: Well, Garbage Pail Kids also changed the history of art, so maybe it's a compliment.

Caroline Framke: It seems like every other minute in Popstar there's a different cameo. Who did you know you definitely wanted to include when you started?

Jorma Taccone: Nas was named in the script.

Andy Samberg: A lot of people were! We were like, "It would be great to get that person," and then … we got them.

Akiva Schaffer: I mean, everybody that's in the movie we asked to be in the movie. [laughs]

Andy Samberg: They were all specific folks that we thought would be good for what we were trying to pull off, and we had very little resistance. It was very nice.

Akiva Schaffer: Seal was a surprise. We didn't have any inclination that he would want to do the movie, but we wrote him into the script and crossed our fingers that he'd want to. Then he showed up, and we still weren't even sure how much he'd be game to do. And then he just did everything and was just a delight to be around.

Jorma Taccone: Everything — allowed a vicious dog to bite his arm. Granted, while wearing padding, but he was just game for all of it.

Caroline Framke: I would also like to formally request a prequel for Joan Cusack [who plays Conner's hard-partying mom]. She was so amazing in the 30 seconds we saw of her.

Akiva Schaffer: An origin story?

Caroline Framke: Yes, please.

Jorma Taccone: There will be a lot of stuff on the deleted scenes for this movie. There's about an hour and a half of footage, and there's a bunch of stuff with her that unfortunately ended up on the cutting room floor.

Andy Samberg: We loved her. She's so fuckin' funny. There was a time when the movie started more like Conner's childhood backstory and she was sort of the tour guide through that. It was so funny, but it was taking too long for the movie to get started, so unfortunately we had to tighten it up a lot.

Caroline Framke: I really appreciated the … short running time. I was trying to think of a way to say that without it sounding like an insult, because it really isn't.

Andy Samberg: No, we get it. We were really conscious of that and intent on keeping it tight. You know, we didn't want to overstay our welcome, especially with the mockumentary format. We felt like keeping it under 90 minutes was a good idea.

Caroline Framke: So you guys know something about creating videos that the internet appreciates, and now with Popstar you've combined that skill with Conner's bubble of pop stardom. If you were giving someone advice on how to become a viral pop sensation, what would you say?

Jorma Taccone: Keeping it short is good. People's attentions spans are … not that long.

Andy Samberg: Yeah, keep it short. Luck out on the timing. Make something people actually really want to see, which you can never tell. For us, it's always down to whether it's funny or not, and sometimes people find it really funny and other times they only find it kinda funny. So it's a crapshoot. There's no real formula other than to just keep making stuff that makes you laugh or that you find interesting, and hope that people connect with it.

Caroline Framke: What I liked also about Conner's approach — if you can call it that — to his stardom is the way he vlogs every little moment of his life.

Jorma Taccone: Like on Snapchat, where everyone has their own reality show now?

Akiva Schaffer: We watched a lot of pop documentaries, went into everybody's Instagrams, Twitter, Snapchat…

Jorma Taccone: But then there are a ton of people just recording themselves on tour, not even as a documentary, necessarily. Like, Wiz Khalifa has a five-minute thing that he does in different cities, A$AP Rocky has an informal kind of doc. But anything that we could get an idea from, we watched. Also just because we're fans of all those people, too. We wanted to see what their lives were like.

Caroline Framke: That's definitely something that's changed in even just the past few years, I think. Instead of being perfect people onstage, they're bringing you into their own mess.

Andy Samberg: Yeah, and has that become the norm, to invite everyone just into your personal life, through Snapchat and social media? The number of people who are like, "This is my house! This is my bedroom!" And we got hooked on that same stuff. It's fascinating.

You want to know how people are living, and what their taste is, and how they feel about their success. But it's also asking a tremendous amount of people in terms of how they connect with their fans, and it feels very intimate and very personal.

Jorma Taccone: And with a lot of people, it feels like it becomes a full-time job doing that. It's kind of crazy to think about just how much people have to do.

Caroline Framke: One thing I was sort of randomly curious about was the story behind Conner's tattoos.

Jorma Taccone: All original, obviously. Made for the movie. [To Samberg:] What does the one on the back of your neck say?

Andy Samberg: I think it says "incredible thoughts," with an arrow pointing up.

Jorma Taccone: [laughs] Oh, yeah. We had a bunch of different ones for that one.

Andy Samberg: There's also a list on my forearm, and all the words start with "Conn." Like, "Connfident."

Jorma Taccone: They're all positive, except for one.

Andy Samberg: Yeah, one says, "Connform," and then in parentheses, "(don't)."

Popstar is now playing in theaters.

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