To Collaborate Productively, Disagree Toward The Same Goal (And Work With Michael Bolton)

That’s one big lesson from the prolific, viral phenomenon known as Lonely Planet.

To Collaborate Productively, Disagree Toward The Same Goal (And Work With Michael Bolton)

Lonely Island invented the Internet.


Okay, that might be a little strong, but Andy Samberg, Akiva Schaffer, and Jorma Taccone created one of the first “viral” Internet sensations, the beloved Lazy Sunday, a digital short that breathed new relevance into Saturday Night Live.

As they’ve grown in popularity, they’ve become known for working with A-list talent–see the auto-tuned majesty of “I Just Had Sex,” their 2010 collab with Akon. The group has since left SNL to pursue other projects, but they remain on the Lonely Island beat. The Wack Album, released last week, is their third–featuring guests like Pharrell Williams, Hugh Jackman, and Most Creative Person Kendrick Lamar.

And they are still very, very funny, as evidenced by their amazingly absurd appearance on Between Two Ferns With Zach Galifianakis.

But how can a trio of dudes continue the funny? The proof is in the pudding; or, more precisely, in their recent interview with SplitSider.

Maintain relationships

Though they’re no longer part of SNL‘s “funnel of productivity,” the guys are still working with producer Lorne Michaels’ show and sometimes airing their videos.


One case, as Samberg explains, was when Maroon 5 frontman Adam Levine was hosting but didn’t have a singing part–the musical guest was Kendrick Lamar. Michaels hollered at them about maybe doing a song together. Lonely Island was in the middle of making the album, so they decided to do a five-way collaboration.

With stellar results.

YOLO (feat. Adam Levine & Kendrick Lamar)

Keep a variety

Like many freelancers, the guys from Lonely Island have a range of projects going on: Samberg’s in a new Fox sitcom called Brooklyn Nine-Nine, Schaffer directed Hot Rod and The Watch, and Taccone appeared on Girls.

This, Schaffer explains, is key to the groups sustainable hustle: Even when they do stuff they really love with other people, it’s not same. “I think if we just did this all the time,” he says, “then it maybe we would be in trouble, but going off and doing other things reminds us it’s more fun to work with your friends.” And that fun comes through when you get Michael Bolton belting out Pirates of the Caribbean anthems.

Jack Sparrow (feat. Michael Bolton)

“If it’s two different things, that’s when you get fucked”

As Samberg explains, the guys in Lonely Island all have really similar taste–that’ll happen when you’ve been together since middle school. That taste is characterized by maximal ridiculousness and, increasingly, clever social commentary–notice how the Galifianakis’s video supports gay marriage in a, how do you say, unfamiliar way. If the Island were a startup, they’d be GitHub: a group of anarchic creators united by an aesthetic. Samberg describes their style:


We prioritize the same things in terms of what we want out of the work we do together, so even if we have a small disagreement, it’s always disagreeing towards the same goal. It’s never, like, “I want this out of what we’re doing and I want this out of it.” If it’s two different things, that’s when you get fucked. The thing that we actually want is the same end product. And it’s just the ebb and flow of getting there.

So there you have it: To be productive in collaboration, disagree toward the same goal. And work with Michael Bolton.

[Image: Flickr user Alterna2]

About the author

Drake Baer was a contributing writer at Fast Company, where he covered work culture. He's the co-author of Everything Connects, a book about how intrapersonal, interpersonal, and organizational psychology shape innovation.