‘Dick in a Box’ Was a Double-Edged Sword for The Lonely Island

One of Saturday Night Live’s most popular Digital Shorts might never have happened if Lorne Michaels hadn’t kept pushing.

The Lonely Island—the comedy trio of Andy Samberg, Jorma Taccone, and Akiva Schaffer that was behind the shorts—talked about the origins of “Dick in a Box” in a new episode of The Lonely Island & Seth Meyers Podcast

The music video, which starred Samberg and host Justin Timberlake as an R&B duo singing about exactly what the title suggests, aired as part of SNL’s 2006 Christmas episode. But on the Thursday before the show aired, the song wasn’t even a premise in The Lonely Island’s minds.

“We didn’t have a short on Tuesday, on writing night. We couldn’t think of one on Wednesday,” Schaffer recalled. So they went to Lorne to explain that they were drawing a blank, but he didn’t see the problem—telling them, “It’s just Wednesday.”

“At that point, we had never written that late into the week,” Schaffer explained. “So we stayed up all night Tuesday, all night Wednesday.”

Timberlake had approached The Lonely Island about doing a song as a Digital Short earlier in the week, and they ultimately landed on an R&B track. With that in mind, the group enlisted assistant musical director Katreese Barnes to start working on the music.

But with no spark for what the lyrics would be about, the group returned to Michaels late Wednesday/early Thursday and admitted they were out of ideas. “I remember going into Lorne’s office and saying we’d failed,” Schaffer said.

With less than 72 hours until showtime, the group felt they didn’t have enough time to write and produce a short by Saturday night. Michaels, however, insisted they come up with something, since Timberlake was game. “[Lorne] was like, ‘There’s still three more days,’” Schaffer shared.

Eventually, an idea came to Taccone late Thursday night. “I was in a corner talking to myself, just being like, ‘What if a present was a dick inside a box, like in that movie Diner?’,” he shared.

Once they had the idea, the trio was able to write the song quickly, and even Timberlake contributed some jokes.

“We were tentative on the idea,” Schaffer notes. “And [Timberlake] was like 100 percent confident. Probably more confident than I’ve ever been about anything creative we’ve ever done.”

The song was written and recorded into Friday morning, and the video was shot during the day on Friday. 

The last-minute nature of the sketch also wound up influencing the video. “You can’t pull permits from the City of New York at 3 in the morning Thursday night for a 9-in-the-morning Friday shoot,” Schaffer noted. “So that’s also partially why it’s just like the Hudson River and stuff. Because you just have to go outside and start filming.”

While the end of the video depicts Samberg and Timberlake being arrested by police officers and placed in the back of a cop car, Schaffer revealed that that was never part of the plan. 

“They were just real on-duty NYPD officers that saw we were doing a thing, and just came and hung out,” he says. 

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“Dick in a Box” went on to become a massive hit, beginning with an enthusiastic response from that night’s audience and hitting the singles charts in both Canada and Australia. The song even won an Emmy Award for Outstanding Original Music and Lyrics. It was the first of many nominations SNL has had in the category—a legacy the show is hoping to keep alive this year.

However, the success of the short was something of a double-edged sword for The Lonely Island. “The fact that we didn’t come up with ‘Dick in a Box’ until Thursday cursed the rest of our time at SNL,” Schaffer said, as it convinced Michaels that “it was never too late for us to think of not just an idea, but maybe the best idea we’ve ever had.”

“There was no amount of time that was too small… because we came in so sure we were out of time, and then turned in ‘Dick in a Box,’” Schaffer concluded. “We could never be trusted again.”

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