Throughout Saturday Night Live’s nearly 50-season run, the series has brought out some very memorable musical guests who rocked the studio and sketches that you can’t help but laugh at no matter how many times you’ve seen it. For example, “Dick in a Box” -- the digital short featuring Andy Samberg and Justin Timberlake, initially aired in 2006 but is shown for every single Christmas compilation episode -- is an irresistible fan-favorite. While it's not one of the most popular SNL clips on YouTube, it's certainly one of the show's incredibly iconic digital shorts. However, Samberg recalled a time he completely botched a live performance of it.
During an episode of The Lonely Island and Seth Meyers Podcast, the hosts got to talking about the sketch, and Samberg looked back at the time he performed the song with Timberlake at New York’s famed Madison Square Garden back in 2007. Before the performance, he was pretty jazzed about it, and I can’t say I blame him:
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.
Despite being excited for the performance, it did not go as planned when it came time to actually do it in front of thousands of people. Samberg recalled how the in-ears he had never used before fell off, and he had no idea what to do next, meaning that thousands of people are seeing him absolutely screw up the performance:
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.
That was only just the beginning, unfortunately. The Brooklyn Nine-Nine alum went on to share details of what happened for the remainder of the performance and how people reacted afterward. He did take it like a pro, though, but hopefully, it didn’t crush him too much. However, it does sound like it’s stayed with him for almost 17 years, even if the other members of The Lonely Island were laughing about it:
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.
Since that was Andy Samberg’s first time using the in-ears and doing a live performance at that capacity, it’s not surprising to hear that there were some kinks in the plan.
In-ears are vital to hearing directions and sound, and without them, musicians wouldn’t know how they sound or where to come in. Regardless, even professional artists mess up every once in a while. It is also nice to hear that people were just laughing after Samberg got off stage and they weren't angry that he messed it up because sometimes, you just have to laugh.
Now that much time has passed, maybe Samberg and Justin Timberlake can reunite again and perform “Dick in a Box” live. It's a great sketch featuring an A+ host and it needs to happen. JT is currently on tour through December, so it's not outside the realm of possibilities. Especially after hearing the SNL alum talking about the nightmare performance, it would be fun to see him come back and nail it.
In the meantime, though, the legendary song is available to watch on YouTube whenever or with a Peacock subscription, along with many other festive sketches. “Dick in a Box” remains one of the best SNL sketches and botched performances will definitely not change that.
