From “Lazy Sunday” to “Dick in a Box” to “Jizz in My Pants” to “Jack Sparrow,” 101 digital shorts were made by Andy Samberg, Akiva Shaffer, and Jorma Taccone — a.k.a. the Lonely Island — for Saturday Night Live between 2005 and 2012. In March of Samberg’s final season, Seth Meyers, SNL’s head writer at the time, had an idea: a bracket, voted on by the staff of the show, to determine the greatest digital short of all time. Now Meyers has agreed to explain for the first time ever how it all went down — and to reveal the winner.
The Lonely Island’s digital shorts were produced independently by the trio, so Meyers and the SNL staff were (mostly) impartial judges. “People chipped in and helped, but [the Lonely Island’s members] were their own sort of fiefdom,” Meyers says. “We were all just consumers of their work. They were part of a really great era of the show. There was something sentimental about going back and looking at the amount that they’d done.” One preemptive warning from Meyers: “I’m going on the record to say the world liked ‘Laser Cats’ more than Seth Meyers.”
Because it was March Madness time, Meyers knew he wanted to do a full 64-seed bracket. He was originally going to do “the NIT of digital shorts” for the ones that didn’t make the cut, but he had “already sunk enough time into those 64.” (By the way, he knows which short would have finished in last place: “There’s one called ‘Daiquiri Girl’ that’s considered by everybody to be the true bottom.” In it, Samberg sings the titular song as scrolling text explains to viewers that Lonely Island knows how terrible the short is and that it was thrown together at the last minute when Gnarls Barkley backed out of the better one they’d planned to make. “Lorne really pushed them to do one that week, but they had nothing,” says Meyers. “So they tried to put out the most offensive thing ever to teach Lorne a lesson.”)
So the first step was to pick and rank the top 64. “It was based more on others’ perceptions than my own personal taste,” Meyers explains. “I started with ‘Lazy Sunday.’ That’s what got the ball rolling. And then the other one-seeds were ‘Dick in a Box,’ ‘I’m on a Boat,’ and ‘Jizz in My Pants.’ Those seemed like big, important ones.” Before long, he had seeded the rest. Here’s what that looked like:
Meyers printed out brackets and distributed them to the SNL staff. They picked the winners of the first- and second-round matchups, and Meyers tabulated the results. (Lorne Michaels voted in the first two rounds.) For the Sweet 16, he had another idea. “It was a Monday night [of an off-week], the night of the college-basketball final,” Meyers remembers. “We got pizzas, watched each short, and then everybody would vote. The thing that made it very SNL was that it became not just a celebration of their best work but also a celebration of their worst work” — and eventually the night devolved into a Lonely Island Worst-of Film Festival. “Lorne essentially forced the guys to do a new digital short every week,” says Meyers — a strategy that resulted in brilliance (“Dick in a Box”) and, well, not brilliance (“Nurse Nancy”). “There’s not a lot of time at SNL where everyone sits around without the burden of the show,” says Meyers. “So it was a really fun night.”
(1) “Dick in a Box” (2006) vs. (4) “United Way” (2007)
Of the three digital shorts that Meyers wrote or co-wrote, only “United Way” made it to the Sweet 16. (The other two, “Business Meeting” and “Firelight,” were knocked out in early voting.) Meyers knew that the sketch about what Peyton Manning is really like when hanging out with kids for charity (there’s a lot of pegging children with footballs) wouldn’t make it much further: “I didn’t think it deserved more than this. My memory was: Pretty big win for ‘Dick in a Box.’”
“Dick in a Box” advances!
(2) “Motherlover” (2009) vs. (3) “I Just Had Sex” (2010)
“I Just Had Sex,” the Lonely Island’s ode to sealing the deal, is the group’s most popular video on YouTube, with over 250 million views. But the bracket wasn’t a popularity contest; it was about what the SNL team liked best. And in this matchup, the edge went to “Motherlover,” a “Dick in a Box” sequel that reteamed Samberg and Justin Timberlake as ’90s R&B singers who romance each other’s moms for Mother’s Day. “There’s a real appreciation for the fact that they did a sequel that was arguably better than the first one,” says Meyers. “‘Motherlover’ correctly beat ‘I Just Had Sex.’”
(1) “Lazy Sunday” (2005) vs. (5) “Two Worlds Collide Ft. Reba McEntire” (2009)
“Two Worlds Collide” — in which Kenan Thompson plays a Reba McEntire impersonator who tricks Samberg into having sex with him — is Meyers’s personal No. 1. “It makes me laugh harder than any other digital short,” he says. “It’s so perfect and so stupid, and there are so many moves in it.” Even so, “Lazy Sunday,” the cupcake-filled digital short that opened the door for all the rest, was “just a chainsaw. You’re not going to get past ‘Lazy Sunday.’” Ultimately, “Reba” was a classic five-seed that couldn’t beat the top contenders. “It tired itself out in the early rounds,” says Meyers.
“Lazy Sunday” advances!
(2) “Natalie’s Rap” (2006) vs. (3) “Jack Sparrow” (2011)
“It was Bolton versus Portman in that matchup,” says Meyers. He admits that “Natalie’s Rap,” starring Natalie Portman playing against type as a gangsta rapper (sample lyrics: “I bust in dudes’ mouths like Gushers motherfucker / Pull up to NBC and smack the shit outta Jeff Zucker”), “was pretty awesome when it happened” — but some felt it was too similar to “Lazy Sunday,” and “people were diversifying their votes.” So “Jack Sparrow,” in which Michael Bolton hijacks the hook of a club song to declare his love for the Pirates of the Caribbean movies, won out.
“Jack Sparrow” advances!
(1) “I’m on a Boat” (2009) vs. (4) “3-Way (Golden Rule)” (2011)
“3-Way,” the third digital short to feature Timberlake and Samberg’s R&B guys, this time having a threesome with Lady Gaga, didn’t lose because of any desire to diversify, says Meyers: “Ultimately, ‘I’m on a Boat’ is just a fantastic anthem. It’s their song you’re most likely to hear at a nightclub.”
“I’m on a Boat” advances!
(2) “Shy Ronnie” (2009) vs. (14) “Laser Cats! 3D” (2008)
What a Cinderella run for the 14-seeded “Laser Cats! 3D,” the third of seven fully stupid “Laser Cat” shorts. “It was the George Mason of digital shorts — I constantly underestimated how much people like ‘Laser Cats,’” says Meyers. But they didn’t like it more than “Shy Ronnie,” in which social anxiety prevents Samberg’s Ronnie from properly duetting with Rihanna. “I invite everyone to go back and watch Rihanna in it again,” says Meyers. “It’s one of the greatest guest appearances in a digital short ever.”
“Shy Ronnie” advances!
(1) “Jizz in My Pants” (2008) vs. (4) “Threw It on the Ground” (2009)
You might have thought this one would’ve been “Jizz in My Pants” all the way, since the Lonely Island’s paean to premature ejaculation was one of the group biggest viral hits. (Over 150 million views!) However, “Threw It on the Ground” was helped by a repeat viewing just before the voting. “I bet if people had voted on memory, ‘Jizz in My Pants’ would have gotten it, but ‘Threw It on the Ground’” — in which a proto–Bernie Bro throws things on the ground to show he’s not part of “the system” — “ages really well,” says Meyers. “There was a whole subgenre of digital shorts that were basically ‘Jizz in My Pants.’ But ‘Threw It on the Ground’ lives on its own.”
“Threw It on the Ground” advances!
(2) “Iran So Far” (2007) vs. (3) “Great Day” (2010)
“I really, really loved ‘Great Day,’” says Meyers of the short starring Samberg as a guy who manages to stay optimistic about his crappy life thanks to cocaine. “But ‘Iran So Far’ is something else.” In it, inspired by Mahmoud Ahmadinejad’s 2007 “No gays in Iran” speech, Samberg performs a romantic rap ballad aimed at the then–Iranian president in what Meyers calls “the most political digital short of all-time, by far. I still get goosebumps when Andy says, ‘But you’re in New York City now, baby,’ and the audience cheers.”
“Iran So Far” advances!
(1) “Dick in a Box” (2006) vs. (2) “Motherlover” (2009)
Do you believe in miracles? In a major upset, “Motherlover” beat its predecessor. “It really did answer the age-old question, ‘What’s more outrageous than a dick in a box?’” Meyers says. “It’s two guys fucking each other’s moms. And they’re Patty Clarkson and Susan Sarandon. What’s going to beat that?”
(1) “Lazy Sunday” (2005) vs. (3) “Jack Sparrow” (2011)
“Jack Sparrow” aired less than a year before the bracket was done, so Meyers thinks its recentness helped it win here, plus Michael Bolton’s appearance had “the best no-one-expected-this turn from a cameo.” Still, though, “it broke my heart to vote against Chris Parnell, the MF Doom of comedy rappers,” says Meyers.
“Jack Sparrow” advances!
(1) “I’m on a Boat” (2009) vs. (2) “Shy Ronnie” (2009)
Despite Meyers’s “unflinching admiration for Rihanna and everything she does,” he acknowledges that “the core song in ‘Shy Ronnie’ can’t hold a candle to ‘I’m on a Boat.’” “Shy Ronnie” has the better turn and the lyric “he pissed himself,’’ which Meyers thinks should be carved on Samberg’s tombstone. But “I’m on a Boat” is “tremendously stupid from start to finish.” Still, Meyers would like to say, “If Rihanna ever reads this, it was all a lie and I was a ‘Shy Ronnie” guy the whole way.”
“I’m on a Boat” advances!
(4) “Threw It on the Ground” vs. (2) “Iran So Far” (2007)
“Threw It on the Ground” may have aged well, but “Iran So Far” is timeless, says Meyers. “Fred [Armisen] is so small and perfect [as Ahmadinejad],” and “Adam Levine is absolutely delightful” singing the hook. Meyers also laments the guest appearance that never quite came together: “Kanye was the musical guest [the week that “Iran So Far” aired]. They had asked him to do it, and he said no. And at good nights, he said to Andy that the short was really good, but he was so happy he didn’t do it.”
“Iran So Far” advances!
(3) “Jack Sparrow” (2011) vs. (2) “Motherlover” (2009)
“Jack Sparrow” has its high, silly concept, but “Motherlover” just had better jokes. Meyers recalls the moment when Patricia Clarkson, playing Timberlake’s mom, turns a photo of Justin facedown on her bedside table, but then Samberg flips it back up: “It’s a move you think you’ve seen before, but then it’s like, Oh, fuck this is great.” Or at the beginning when they’re “rapping lightning fast, and they both look so fucking stupid. And then they’re eating sandwiches in the park, talking to each other. It really is just fantastic.”
(1) “I’m on a Boat” (2009) vs. (2) “Iran So Far” (2007)
Meyers says that because the voters were Lonely Island’s co-workers, they were occasionally prone to bias. “For ‘Iran So Far,’ I think it was helped by when it ran,” he says. “It was the season premiere, and that was a great year at SNL. Everyone got along really well. So, when we were voting, that reminded people of a really happy time on the show.”
“Iran So Far” advances!
(2) “Motherlover” (2009) vs. (2) “Iran So Far” (2007)
“This one was super-close,” says Meyers, but “Motherlover” won the day. The voters were “writers who knew how much a challenge it was to have to top ‘Dick in a Box.’ Timberlake came back to the show, and everyone knew that they had to try, but we all sort of figured it wouldn’t be as good as the first one. So anyone who’s ever had to write the second version of anything was so impressed.”
Still, Meyers says he never expected “Motherlover” to win it all. “I picked the one-seeds for a reason,” he says. “I thought ‘I’m on a Boat’ would have won. And I think in the end, what ‘I’m on a Boat’ doesn’t have is the insanely great moves of ‘Motherlover.’ ‘I’m on a Boat’ is a really great comment on the anthemic club song, which was the sort of observation they always did really well. But ‘Motherlover’ was a sequel better than the original, really catchy, and then it had so many good jokes within it.” The choice can be no other.
Winner: “Mother Lover”!
This story originally ran in 2016 and has beeb republished in honor of the tenth anniversary of The Lonely Island’s Incredibad.