Why The Lonely Island's "I'm On a Boat" Digital Short "Haunts" Jorma Taccone

Andy Samberg and Akiva Schaffer, two of the three The Lonely Island members.

Samberg recalled that he and Schaffer were hanging out with an old friend, messing around with the beat they wanted to write to and "I just started yelling, 'I'm on a boat!'" 

"I remember Keev started laughing and I started laughing. We were like, 'Guess that's the premise!'" he continued. "Obviously, there was a lot of boat stuff in rap videos at that moment in time." 

The two began writing their individual verses, assuming they'd eventually heighten the premise and find a twist, but in the end it was simply a song about being on a boat. 

It didn't win, but the song nabbed a 2010 Grammy nomination. Samberg and Schaffer kindly gave Taccone a writing credit, so he's included in the nod.

As Schaffer noted on the podcast, it was not nominated for comedy, but Best Rap/Sung Collaboration thanks to T-Pain's participation. Schaffer and Samberg attended the show with their sunglasses on the entire time ("because it was rock & roll"), and said they only agreed to go because they knew "Run This Town," by Jay-Z, Rihanna, and Kanye West, would definitely win. (It did).

"I don't know if anyone's ever gone to the Grammys hoping to lose more," Schaffer said. "We were like, if we win, we can't get on stage. We were only confident enough to go because we were that sure that we were going to lose." 

Yes. As they said on their podcast, they filmed on a real yacht in Miami, Florida — and had to use half their budget on a private plane for T-Pain, who was worried about weather on the Canadian leg of the tour he was on. 

Samberg and Schaffer didn't get to actually live the life of a famous rapper on a yacht, but they described the shoot as a sort of "fantasy camp" where they were "pretending debauchery," which Schaffer called "cosplaying at the highest level." 

This was before drones were widely used for filming, so a helicopter had to be used to film the boat in the water. The helicopter pilot was a "ex-Vietnam pilot who had done this thousands of times," Schaffer recalled, but they had to go way out into open ocean and share GPS coordinates because helicopters weren't allowed in the bay where they were initially filming.  

"So now we're out in open water where it's way rockier and the boat is moving way more," Schaffer said. "And we have to go climb out onto a part of the boat where you're not supposed to be standing, in dress shoes. They put rubber on our shoes so that we hopefully don't fall off into the water." 

Taccone hid from the cameras on the inside of the boat while speakers blasted the music, though the sound and extremely close proximity of the helicopter made it hard to hear. 

"Even T-Pain was looking at us like, 'Holy s---, what are we doing?'" Schaffer remembered. 

The shoot was already chaotic, but Schaffer had asked for director of photography Aaron Platt to make the video look "frenetic" by popping the lens in and out. The result was a bunch of footage that looked terrible, and Samberg remembered Schaffer panicking and having to spend way more time editing than he usually did because there was very little clear footage to choose from. For every shot that made it into the video, there were no alternatives, and many planned shots had to be switched out in the edit. 

"When you see the finished product, you would never know it because it's so high energy and dope," Samberg said. "And in the end, I'm actually glad it was shot that way because it gives it this freneticism that is f---ing incredible." 

"I'm on a Boat" appears in Season 34, Episode 15, hosted by Bradley Cooper with Musical Guest TV on the Radio. It aired on February 7, 2009.

Watch that episode, and every season of SNL, on Peacock anytime.