“I Never Recover”: Andy Samberg Once Bombed “Dick in a Box” Live With Justin Timberlake

When you’re lucky enough to have a viral hit song, and it happens to be with a pop music superstar, and then you get a chance to perform it at Madison Square Garden … and you utterly blow it.

It’s a story Andy Samberg just told on The Lonely Island and Seth Meyers Podcast on Monday.

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The song was “Dick in a Box,” the risqué 1990s R&B parody that premiered on Saturday Night Live in 2006 as a digital short (along with 16 bleeps) and later racked up 28 million views on YouTube (the original is below). The song was written by The Lonely Island (Samberg, Akiva Schaffer and Jorma Taccone) and songwriter Katreese Barnes, along with that week’s SNL host, Justin Timberlake, spoofing his NSYNC past.

Samberg eventually got the opportunity to perform the song with Timberlake at a show in New York, and that’s where things went wrong. Despite Samberg’s familiarity and comfort with doing live performances, concert performers typically use in-ear monitors to follow along with the track because the audience can be rather loud and distracting.

“Justin hit me up. He’s like, ‘Yo, I’m coming to New York. I’m doing Madison Square Garden. We’re going to do it as the last encore.’ And I was like, ‘Fuck yeah! Oh my God. MSG. This is it!’ So, I went there in the afternoon. We did a rehearsal. We come up through the middle of the stage, all dramatic. And it was the first time I’d ever worked with in-ears … [Timberlake] was like, ‘Just so you know, it gets really loud, so you have to have the in-ears. I was like, ‘I’ll be fine.'”

“In rehearsal, it was super calm and chill,” he continued. “I can hear him perfectly. … I watched most of the show, this is fucking incredible, I was like, ‘I can’t believe I’m about to be on that stage,’ it was 10,000 people going crazy.”

Samberg recalled getting in position under the stage and coming up on the platform. “The place goes fucking insane, it couldn’t have been a hotter move in that moment, [Timberlake] knew what he was doing. I take one step off the platform and both my in-ears fall out. All I hear is [crowd roar]. I’m like, ‘Oh no.’ I’m supposed to sing first. I cannot hear the beat. So I’m just like, I think I know where we are in the song. But I can’t hear myself. And I start like five octaves higher than what I’m supposed to do … I know it’s wrong, but I’m so overwhelmed, and I’m trying to remember where I’m supposed to walk on stage to meet up with him. And he sees that it has happened. And he looks at me like, ‘What?’ I point to my ears like, ‘Ahhh!’ So we go through the rest of it, and I never recover. And I get off, and I get changed, and I come back, and Akiva and Jorma were just dying laughing. It had been a while since I was up there, and they were still laughing … They were like, ‘You sounded so bad! It was trash!'”

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