Andy Samberg recalls bombing live 'Dick in a Box' performance with Justin Timberlake: 'I never recover'

Allow Andy Samberg to explain what went wrong during an ill-fated performance of "Dick in a Box" with Justin Timberlake at Madison Square Garden.

In Monday's episode of The Lonely Island's joint podcast with Seth Meyers, members Samberg, Akiva Schaffer, and Jorma Taccone looked back at the origins of "Dick in a Box," one of their most infamous digital shorts that premiered on Saturday Night Live during the show's holiday episode in December 2006.

When the topic turned to Timberlake inviting Samberg to perform the track during one of his concerts at the New York venue in February 2007, Samberg recalled bombing the performance after both of his earpieces fell out prior to the big number.

"Justin hit me up," Samberg recalled. "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."

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In-ears help performers hear the track they'll be performing to since the audience can get loud and drown out a lot of noise, Samberg explained. “They were loners. But at rehearsal, it was like super calm and chill. We're just in a big old empty Madison Square Garden. We come up through the middle. I can hear him perfectly. We're doing all our funny choreographed moves. I'm singing. And we're like, oh my God, it's happening."

When Samberg appeared on stage for the big performance, however, “I take one step off the platform and both my in-ears fall out. I'm like, oh no. I cannot hear the beat. I'm supposed to sing first. So I'm just like, I think I know where we are in the song. And 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," he continued. "And I'm trying to remember where I'm supposed to walk on stage to meet up with them. And he sees that it has happened. And he looks at me like, what What? I point to my ears like, 'Ah!' 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.”

Samberg swore that he "sounded good at rehearsal," adding, "I was just so green that I didn't even know to be like, I have to find those in-ears and put them back in."

"Dick in a Box" introduced Samberg and Timberlake as '90s R&B artists singing about gifting their girlfriends their dicks in a box as a holiday present. It premiered during the Timberlake-hosted episode of SNL in December 2006 and won an Emmy for Outstanding Original Music and Lyrics the following year.

Listen to the "Dick in a Box" podcast episode above.