The Lonely Island joined Saturday Night Live in September of 2005 (Andy Samberg as a cast member, Jorma Taccone and Akiva Schaffer as writers) and three months in, they secretly filmed “Lettuce,†their first digital short, without Lorne Michaels’s knowledge. They eventually showed it to him and he agreed to air it and encouraged them to do more. It was their next one, “Lazy Sunday,†which put them on the map. From that point on, Lonely Island’s digital shorts helped define the next seven seasons of SNL. We all know the huge ones — “Dick in a Box,†“Iran So Far,†“Laser Catsâ€Â — and the many Lonely Island music videos. However, with this week’s release of the group’s highly anticipated third album, The Wack Album, we thought it was a good time to look back at the less-well-known digital shorts. Here are our ten favorites.*
“Doppleganger†(Aired on March 11, 2006)Â
Though “Lazy Sunday†was huge, it still wasn’t until the back half of that season, after “Natalie’s Rap,†which aired on March 4, that we saw digital shorts more consistently. “Doppelganger,†in which Seth Meyers, Will Forte, and Andy Samberg point out nearby look-alikes, has a homemade feel to it and quickly and absurdly escalates into violence — two features that many digital shorts will possess.
“Harpoon Man†(Aired on October 21, 2006) Â
“Harpoon Man†features John C. Reilly as a badass, Shaft-like hero and Andy Samberg as the guy singing his theme song. The premise is silly enough, but what makes it squarely a Lonely Island joint is the quick reveal that Samberg is actually parodying those types of songs to immaturely make fun of Harpoon Man.
“Business Meeting†(Aired on February 24, 2007)
This one works because of just how short and quick it is. It gets in, runs through some very weird and bizarrely specific characters (Mountain Joe, Captain Pajama Shark, Chief Big Cloud Gary), and gets out. The guys have always been good at not beating a joke into the ground unless that’s the point.
“People Getting Punched in the Face Before Eating†(Aired on October 13, 2007)
It’s hard to know exactly why this short works. It might be the funny little details along the way (Bon Jovi jumping up with a flying-V guitar, the streak of the banana on the window, etc.) or the classic Lonely Island complete-left-turn kicker. Or it might just be that it’s oddly gratifying to watch someone punch people and then be super amped about it.
“Hero Song†(Aired on March 8, 2008)
“Hero Song,†in which Samberg plays a wealthy businessman who sings a song about becoming the city’s superhero, features one of Lonely Island’s slowest builds to a punchline. When it gets there, it pushes repetition to its extreme. It, like many shorts, undercuts a cliché or trope.
“Extreme Activities Challenge†(Aired on October 4, 2008)
Consisting of Kristin Wiig and Andy Samberg competing in silly challenges (hat balance, shoe hands, etc.), this might be the digital short that was the most fun to shoot. Where a lot of the most famous shorts seem like they took time to plan and execute, some of the best feel like they were shot day of, in a break between lunch and dress rehearsal.
“Everyone’s a Critic†(Aired on November 15, 2008)
Almost like an episode of Mr. Show, “Everyone’s a Critic†does a great job of repeatedly using misdirection to end the sketch far from where it began. Somewhere in the middle, Andy Samberg and Paul Rudd paint each other, which directly results in classic digital short chaos.
“Doogie Howser Theme†(Aired on January 10, 2009)Â
Getting the entire cast to dress up like Doogie Howser and pantomime playing instruments to that show’s theme is probably the simplest idea of any of these. It’s not laugh-out-loud funny, but it’s a good time and taps sweetly at nostalgia.
“Party at Mr. Bernard’s†(Aired on December 4, 2010)Â
By 2010, the Lonely Island were a thing, and as a result many of the shorts from the 35th and 36th season doubled as music videos for the group or were super popular. “Party at Mr. Bernard’s,†a “what would really happen?†Weekend at Bernie’s parody, got lost in the shuffle. You might ask, “Why would they parody a 20-plus-year-old dumb movie?†It’s that exact nonsensical stupidity that makes it work.
“Best Friends†(Aired on December 10, 2011)
By Andy’s last season, Lonely Island were so popular that Jorma Taccone and Akiva Schaffer were too busy to work on SNL full-time. Shorts were handled often by John Solomon, with Jorma and Akiva popping in periodically. “Best Friends†was a Lonely Island joint and the best short of the season. It’s a surprise that this song, about two pals who slowly pick up more and more, crazier and crazier friends (including Matt Damon and Val Kilmer, playing a handsome drug addict and brilliant lunatic respectively), wasn’t a bigger hit.
* To be clear, these are only the digital shorts from the time that were produced by the Lonely Island guys. As a result, fantastic shorts like “Japanese Office,†which was written by John Lutz and Marika Sawyer, or “Body Fuzion,†which was written by Amy Poehler, Maya Rudolph, and Kristen Wiig, are not included.