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How the Lonely Island Mastered the Fine Art of Being Dumb on Purpose

The Lonely Island Photo: Vulture and Getty Images

It’s been over seven years since the Lonely Island’s Andy Samberg, Akiva Schaffer, and Jorma Taccone all left Saturday Night Live, the place where they, as we’ve written, “Changed the Internet, Comedy, and Especially Internet Comedy” with their digital shorts and fraps (fake raps) that were both hilarious and deferential to the history of hip-hop. A lot can happen in the better part of a decade. While each of the three Islanders maintain busy careers, they still come together to create ambitious projects including The Wack Album in 2013 and their cult canonized full-length feature Popstar: Never Stop Never Stopping in 2016. Their new project, The Unauthorized Bash Brothers Experience, a Netflix “visual poem” and mixtape about shamed Oakland A’s home-run kings Jose Canseco and Mark McGwire, is a bit of a throwback their SNL days, with the guys shooting on a super-low budget and being driven just by what they find funny.

The “Jose & Mark” song in particular, which they also performed at their first-ever official live show at Clusterfest almost exactly a year ago, is the jumping-off point for a special Thursday edition of Good One, Vulture’s podcast about jokes and the people who tell them. We talked with principal creators Samberg and Schaffer (the Lonely Island operate a bit like Animal Collective; if two or more are involved, it’s a Lonely Island project) — who play Canseco and McGwire, respectively — about how they write their rhymes, hero worship, Lonely Island’s live shows, and their new roles as TV and film producers. Read a short excerpt from the conversation or listen below. Download the episode from Apple Podcasts, Spotify, or wherever you get your podcasts.

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What was your journey in thinking about the Bash Brothers — from them being heroes to kids to the steroid stuff to being public figures yourself?
Andy Samberg: I was as big a fan of the Bash Brothers as a kid can be. Growing up in the Bay, everyone was completely ignited by them. I put them up there with “Showtime Lakers” and those kinds of dynasties where there’s just something special about it — the personality combined with the talent and the story built around that. We do a lot of deep, deep sarcasm on this thing, but there is also truth to the idea that they work in a job where there’s enough pressure that you would try things like that.

When I first interviewed y’all, Akiva, you said that you guys like “making fun of posturing and pretending to be cool and tough and masculine.” How are the Bash Brothers muses for your style?
Samberg: Yeah. They definitely embodied that ’80s vibe that is both really fun and entertaining to watch and behold, but also has more and more and more become clearly problematic.

Akiva Schaffer: That’s not even specifically them. We could have been any sports star from the ’80s. The whole thing is almost as if we stopped learning anything when we were 11. It’s what our dream of what their lives were like.

Samberg: It combined with a lot of realizations about stuff we grew up on. We had discussions about Revenge of the Nerds and all these movies that we grew up on that seemed really harmless and goofy. And then you watch them [later] you’re like, “Oh, this is rapey as fuck. How were we shown this as children?”

There’s nothing about Mark McGwire or Jose Canseco that we would assign that to, but we loved them and they acted as this vessel through which we could explore how growing up in that era made us feel. So while we’re huge fans of theirs, we’re also talking about why things were bad.

Why was a “visual poem” how you chose to play with this idea?
Samberg: We looked at ten songs we had and went, “Do we just drop them on SoundCloud or as an album on Apple Music and see if anybody notices?”

Schaffer: The main joke of it is, why did we make it? Then the more you make of it, the funnier the joke. What’s the most fancy, highfalutin pedestal we could put this thing on?

Samberg: We kept coming back to the idea of the long-form video, which had this huge resurgence. Basically everyone who writes about this correctly is comparing it to Lemonade, but since Lemonade there’s been like 15 other ones. It just felt like the moment to do it that way. As is our proclivity, we like dressing up our turds as fancy as possible.

In my review of your first official show, I wrote about how I was nervous as a fan of yours. It felt like a real tightrope you had to walk. In putting together that Clusterfest show, what kinds of things did you need to figure out in order to make it work?
Samberg: Doing live shows in the context of a comedy festival helps us a lot because, first and foremost, it is a comedy show. The odds are that most people coming have heard a lot of the songs, so we need to think of ways outside of the songs to keep it entertaining and funny. At the same time, we’re told that people do bump the songs both earnestly and ironically — but the line is blurry, and that’s part of the fun of it.

Schaffer: We weren’t exactly sure how fake-cool to pretend to be versus self-deprecating and acknowledging that we’re frappers and crappy. We found a balance that we were very happy with at that show.

Samberg: We are the top frappers in the game. We want to get that term a little more ubiquitous. I’ve coined it, frapping, fake rapping. And I just don’t feel like anyone’s saying it but me.

Schaffer: It could really catch on, then people could use it against real rappers and call them frappers. The thing we’re the proudest of could be an insult to others.

You are about to set out for your first-ever tour. What did you learn from Clusterfest that you’ll bring to those shows?
Schaffer: It’s a careful balance of us being very bored and wanting to cut everything down very small and then being like, “Wait, people have actually paid money and had to get a babysitter. They’re going to be annoyed if it’s too short.” We’re like, “Who would want to see this for more than 45 minutes max?” I mean, the Clusterfest show had to be an hour, and so that felt like the perfect length. But now we’re doing our own, so we have to make it a little longer. We’re constantly being like, “Eh. It felt good at an hour.”

Samberg: Clusterfest helped us learn that there were certain songs people were just happy to hear. We were like, “Man, maybe we’re going to subvert this in some way.” There were some of them where we had a contingency plan if it felt wrong, but then we got out there and it was like, “Oh, no. It just feels right.”

Schaffer: People just wanted to sing along to it, which was a pleasant surprise.

You’ll sometimes describe your stuff as “stupid” or “dumb.” How is your stupid or dumb different than the comedy some critics deride for being stupid or dumb?
Schaffer: I think we just mean silly.

Samberg: I’ll bring it back to when I was a kid, and a teenager and I was obsessed with Adam Sandler and Jim Carrey stuff. I’d be like, “You have to watch this!” and my friends or parents would be like, “I don’t know. It just seems stupid.” I would always say, “Yeah, but they know it’s stupid. That’s the difference.” They’re choosing to be stupid from a place of intelligence, and therefore that is making me happy. They’re saying, “We know what the world is, and in spite of that we’re going to spend our time on this as adults.”

It’s the same thing we always used to talk about watching Stella. They would be in suits and ties doing the dumbest thing you could possibly think of, choosing to use their adulthood for turning the world into a cartoon. If you’re the type of person who enjoys that — which we are and we hope that the people who like our stuff are — it’s a choice. It’s saying, like, “We want to make something dumb to make people laugh and smile and feel happy.”

For a while now, the Lonely Island has had a production company, Party Over Here, but this year you had two breakout projects — Pen15 and I Think You Should Leave. What is the goal of having projects you can help with but not be the creative driving force on? What would you like to help put into the world?
Schaffer: I don’t know that we had any thesis statement going in, but I will say in hindsight, on those two specifically, they are both shows that follow exactly what we did at SNL, which is making things that are not pitchable but turn out good. At SNL, we wouldn’t put our things up for table reads because they’re execution-based ideas that could sound terrible. Same with Pen15. They tried to pitch it and we can say it’s not a very pitchable show.

Samberg: We gave them some money to make a presentation. They came back with their presentation and we were all like, “Oh, fuck. They’re so good.”

Schaffer: By the way, even with the presentation, a ten-minute version of it, we still had a lot of difficulty getting it sold and on the air, and we had to make it.

Samberg: The cool part of it is helping people that have a really unique perspective make something. I’m not saying we wouldn’t do things outside of this scope. We love broad comedy, we love niche comedy, but the thing that generally has a harder time getting made, especially right now, is comedy for the sake of comedy — the place in the world where it’s just for people who live and breathe comedy and want to laugh and want to get surprised by some weird thing. Then you have a show like Pen15, which elevates past that because they’re actually really brilliantly weaving in social commentary and emotion and stuff like that that breaks your heart. But the thing about that show that initially struck us was like, “Holy shit. These guys are funny. This is hard laughs, fucking funny.” Physical joke writing. Obviously Tim [Robinson] as well.

Schaffer: For the record, if somebody had a really good idea for a multi-cam on CBS that would run like six, seven seasons, 22 a season, we’re fine with that. We’ll be at upfronts celebrating it and we’ll cash those checks.

How does the Bash Brothers project point toward the future of Lonely Island?
Schaffer: I don’t know, but we always stick to one rule. And it’s: Is this making us laugh right now? That has been it from the jump.

Samberg: And anytime we’ve strayed from that, we’ve regretted it. For all I know, we’ll do another fully straightforward Lonely Island record; I think that could be super fun. We might do another movie that’s for a studio if that comes up and we have an idea we’re excited about. It’s really what’s making us feel inspired and excited that day.

How Lonely Island Mastered the Art of Being Dumb on Purpose