The Secrets Behind 'Dick in a Box' & More: Andy Samberg, Justin Timberlake on the Viral Hits of 'SNL'

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Andy Samberg and Justin timberlake during "Dick in a Box" skit on December 16, 2006 on Saturday NIght Livei

In an exclusive excerpt from the newly updated Saturday Night Live book Live From New York, Justin Timberlake, Andy Samberg and other key players break down two of the most iconic musical moments in the show’s history.

'LAZY SUNDAY'

The first breakthrough Digital Short featured castmembers Andy Samberg and Chris Parnell rapping about their quest to smuggle cupcakes into a matinee of The Chronicles of Narnia. Recorded and edited in just two days, "Lazy Sunday" originally aired on Dec. 17, 2005.

ANDY SAMBERG, castmember: I started watching the show when I was 8 years old. When I started watching, it was people like Dana Carvey and Jon Lovitz and Phil Hartman, and then Mike Myers came in and obviously "Wayne’s World" was huge for me. And then the next wave that impacted me the most was [Adam] Sandler, [Chris] Farley, [David] Spade and Chris Rock.

LORNE MICHAELS, executive producer: I guarantee you that Andy wanted to be Sandler.

COLIN JOST, writer-castmember: "Lazy Sunday" was a huge hit. There hadn’t been people doing songs on our show that way probably since Adam Sandler. So it was a combination of a new style, editing it in a funnier and tighter way and also the music component, which was so strong on its own and was done so well.

AKIVA SCHAFFER, writer: We did "Lazy Sunday" in December of 2005, and by the end of the weekend my brother emailed me and told me, "Look at this place where you can watch it online." Because at that point you couldn’t watch SNL clips online. NBC wasn’t putting anything online after it aired or anything like that. So I was just excited because it was Sunday and I hadn’t seen it since we had aired and I was like, "Oh, I get to watch it again." And that was YouTube. I have no idea to this day who posted it. And over the next week, as it became kind of a news story, everybody discovered the video and a lot of people discovered YouTube through the video. And it was by far the No. 1 thing on YouTube, but the numbers were not like, obviously, what they are today.

JORMA TACCONE, writer: Because "Lazy Sunday" became so popular, I think we garnered a lot of trust from Lorne and that allowed us to do whatever we wanted to do. And also it wasn’t a huge risk because we weren’t spending a lot of money. "Lazy Sunday" cost the amount of whatever we spent on videotape and taxi rides to the Upper West Side to go to a theater — cheaper than building sets for a sketch by far. We eventually started getting budgets and shooting things on better cameras and having crew, obviously. In fact, that happened pretty quickly.

SAMBERG: Up until the year before we got hired, we were still recording SNL on VHS tape so we could rewatch sketches we liked. People always joke to us about how we made YouTube huge, but I think we were more just fortunate in having incredible timing — that we happened to have something people really wanted to watch at the moment computers got fast enough to stream it.

TACCONE: So this was the beginning of wanting to see every week how popular something was, because for the first time I think we could quantify the popularity of something we had done in digital hits and downloads.

MICHAELS: And then NBC had the classic NBC reaction: [It] sued YouTube. It was suddenly on the front page of the business section [of] the [New York] Times, that this startup called YouTube was being sued by NBC. You know, you would think that somebody would have gone, "Let’s just buy this thing or figure it out."

NBC announced at every upfront some new digital strategy, but they didn’t have any strategy, obviously, and I wanted SNL.com. I said, "It’s idiotic. No kid goes to a corporate site and looks for a show." But they were so fierce about it — "We’re building our synergistic NBC.com." And so we weren’t allowed to break away. We thought that would have been revolutionary. We would have been Funny or Die or whatever else there was. But they wanted a corporate identity.

 

'DICK IN A BOX'

Justin Timberlake’s comically productive collaborations on SNL got off the ground with this crooning duet with Samberg about how to give a girl the ultimate gift. In the original network airing on Dec. 16, 2006, the word "dick" was bleeped 16 times.

JUSTIN TIMBERLAKE, guest host: With "Dick in a Box" we had this loose idea. We’re kind of close to the same age so we kind of grew up with that kind of ’90s R&B group sound when we were kids, so we had this idea about those groups and how to do a joke about guys who were still stuck in that era. Which wasn’t a long era — like, half a decade, I think. And so that’s the idea we started off on, and then it was kind of like, "How do you get away with them being idiots?" And the best way was for them to be as genuine as possible about the gift they were giving but not totally being at your full wit.

TACCONE: The first time they showed "Dick in a Box" we were on the studio floor watching and we had this electrifying feeling and we thought, "This is special." We’d thought it was special while we were making it too, and then to feel it had this second life online gave us this other kind of feeling. Getting to work with someone as wildly talented as Justin Timberlake, getting to spend maybe four days with him — like, any time he wasn’t down on the floor rehearsing he’d come up to our shitty little writers’ room and work with us on lyrics. That was amazing. All of it was amazing.

SCHAFFER: "Dick in a Box" we thought was pretty inside baseball. We were using songs that people don’t necessarily know anymore [for inspiration], from a broad SNL-audience point of view, and the joke was crass and stupid. We were not confident in the least. Timberlake was the only one who was confident. We showed him the script for it, and he read it. We were almost embarrassed to show it to him, but he went, "This is great. We’re doing this." I feel like he’s the only one who didn’t have doubts.

TACCONE: It was sort of an order-up kind of thing. Lorne said, "You’re making a musical thing with Justin. Just do it." And we were like, "OK, well, we don’t have an idea." And then it was concept Thursday night, start shooting Friday morning, lose Justin for a period of time, end shooting Friday night into Saturday morning, start editing Saturday morning and keep editing until the moment that it airs. That became our standard for how we made things. I got so good at knowing how much time we had that if we were done filming something and had 15 hours until air, I was like, "I can only sleep for half an hour, not 45 minutes."

JOST: One Timberlake sketch that I wrote with Erik Kenward and really loved, but that we never got to do, was Justin playing Michael McDonald and he opened his own fast-food restaurant and he called it McDonald’s. And he was at a piano in his restaurant and he would sing about the deals and also sing about his legal trouble with McDonald’s, who were constantly suing him. It was like, “My life is a nightmare/We also have Chicken McNuggets.” Timberlake just had the funniest Michael McDonald impression, but we could never figure out how to use it. It’s tough to get things into Justin’s shows anyway, because he has a bunch of characters that are recurring. Things have to really hit to get in.

Excerpted and abridged from Live From New York (Newly Updated and Expanded for SNL’s 40th Season) by James Andrew Miller and Tom Shales. Copyright 2002 by Thomas W. Shales and Jimmy the Writer Inc. Excerpted material copyright 2014 by Jimmy the Writer Inc. Reprinted by permission of Little, Brown and Co. All rights reserved. 

This excerpt orginally appeared in the Sept. 13 issue of Billboard.