The 10 Best Musical Sketches from Lonely Island

The Lonely IslandGetty Images/John Ricard

Now that they’re done sailing on a boat, hugging it and quitting it, and doing the Creep, The Lonely Island boys are finally ready to tackle their biggest project yet: a feature film. The comedy group, made up of Jorma Taccone, Akiva Schaffer, and Golden Globe-winner Andy Samberg, is set to star in and produce a musical comedy for Universal (via Variety). Shaffer and Taccone will also be stepping behind the camera to co-direct the project, and Judd Apatow has also signed on as a producer. Thus far, no information about the project’s plot or title have been released, but based on the three comedy albums and hundreds of Digital Shorts that the team has created over the past decade, it seems likely to contain plenty of celebrity cameos, hip hop influences and people’s junk in inappropriate places. In fact, it wouldn’t be much of a surprise if the group decided to look to their musical sketches for cinematic inspiration; after all, the trio has produced a great deal of ridiculous and memorable characters and more than enough absurd premises to provide the basis for a full-length film. We decided to take a look back at Lonely Island’s 10 best sketches in order to see if we could predict who (and what) is most likely to appear in the upcoming movie. Something’s got to work better than Hot Rod, right? 

10) “YOLO”
Like most of the group’s sketches, “YOLO” relies on a one-joke premise: treating the phrase “YOLO” as a cautionary tale rather than a celebration of adventures. But it’s a great example of Lonely Island’s ability to build on that one joke, moving slowly from “be careful” to “never leave your house” to a terrifying shot of them smiling gummy smiles after pulling out all of their teeth. It also happens to be an incredibly well-crafted pop song, which shows how far the group has come in terms of musicality.
Could It Be a Movie? There might be enough in the premise in order to create a funny side character, but it’s hard to see how much further the guys would be able to take a joke that ends with them cowering toothless in a boarded-up house.

9) “Great Day”
“Great Day” is a rapid-fire barrage of jokes, but what’s great about them is that they all build on each other to tell a complete story. From the first moments when the camera pans through Dennis’ dirty apartment, you already know that the actual song won’t be as upbeat and cheery as the background music. The juxtaposition between the Sesame Street nature of Dennis’ adventure through the streets and what he’s actually singing makes it even funnier when he finally loses it and starts climbing trees and pretending he’s in the Matrix.
Could It Be a Movie? Maybe not a full-length movie, but there’s probably enough tragedy and insanity in Dennis’ life to make an interesting short film.  

The Lonely Island – Great Day from Mike Oxbig on Vimeo.

8) “3-Way (Golden Rule)”
There’s a lot that goes into making “3-Way” such a solid sketch: the idea that these guys would do just about anything to hook up with a girl, the fact that it finally establishes them in a pre-cell phone era, the plethora of multi-colored outfits, the fact that Justin Timerlake’s character met their cutie at a Payless, and then the final reveal that they’re much more interested in each other than in the girl they came to see. It takes the original “D**k in a Box” joke to absurd new heights and throws in a bunch of tiny, subtle jokes to create a sketch that actually gets better the more you watch it.
Could This Be a Movie? Are you kidding? We’d watch anything with Timberlake and Samberg’s R&B wannabes in it, and an epic tale about their love and the girl who came between them has great cinematic potential.

7) “Like a Boss”
“Like a Boss” is another great example of The Lonely Island’s ability to turn a single joke into a chronicle of one man’s breakdown. However, it owes just as much to Seth Rogen, whose incredulous looks punctuate every unbelievable claim that Samberg makes perfectly. It kind of fall apart towards the end as the Boss’ actions escalate, but it’s that middle bit, where Samberg first starts to hint at how messed up he is and Rogen just starts to get uncomfortable, where this sketch truly shines.
Could This Be a Movie? Probably not. The Lonely Island managed to do everything it possibly could with that one joke in two minutes, and any longer would probably ruin things.

The Lonely Island like a boss from lewroll21 on Vimeo.

6) “I’m on a Boat”
Look, “I’m On a Boat” is a pretty dumb song as a whole, but the lyrics are some of the finest Lonely Island has ever written. They’re generally simple – the chorus is just “I’m on a boat” repeated over and over again – but the verse slowly builds from the standard party rap song to rhyming about nautical-themed pashmina afghans in a way that’s truly clever and inventive. Simplistic enough to stick in your head, but complex enough to make you laugh, it’s no wonder it became one of their biggest hits. After all, when was the last time you managed to resist singing this song anytime you were in the same vicinity of a boat?
Could This Be a Movie? Only if it’s about the love story between T-Pain and that mermaid; that’s what we really want to see more of.

5) “Space Olympics”
Less a song than a sketch that happened to have been run through auto-tune, “Space Olympics” is a truly ridiculous, truly epic piece of work that’s most remarkable for the sheer world-building it does in the confines of three minutes. Sure, it’s mostly a joke about the dumb events that would make up a future Olympics, but the glimpses of a resource-lacking, poorly-run sporting event and the incompetent bureaucrat put in charge is a clever, well-crafted piece of satire.
Could This Be a Movie? Definitely. We’d pay good money to see Samberg’s ridiculous ambassador attempt to rebuild the Space Olympics on his own. It’s true underdog story.

The Lonely Island – Space Olympics from Jeff Wiggles on Vimeo.

4) “Dear Sister”
Anyone can parody a soapy teen drama like The O.C., but “Dear Sister” manages to take the single most ridiculous, shark-jumping moment in that show’s history and make it even more absurd and melodramatic. The close-ups, the music, the slow-mo – it all comes together to make a wonderfully surreal sketch that is just the right amount of dumb. Plus it contains what is perhaps the finest performance of Shia LaBeouf’s career.
Could This Be a Movie? Unfortunately, no, but it would make for an incredibly dramatic climax.

3) “D**k in A Box”
Perhaps the greatest use of a one-joke premise in The Lonely Island’s career, “D**k In a Box” is remarkably clever for a song about a dude gifting his junk for the holidays. But as hysterical as the facial hair and smooth falsettos are, the true highlight of the song is its two breakdowns. The ending where the gifting occasions slowly become more and more inappropriate is one of Lonely Island’s best uses of escalation. But it’s the second verse, where the lyrics basically explain the whole joke of the song with slow jam earnestness, that’s the real triumph, as instead of killing the whole premise, it actually just heightens the ridiculousness of the situation.
Could This Be a Movie? You mean someone’s not already making a film about these two idiots?

2) “Lazy Sunday”
The Digital Sketch that kicked everything off, “Lazy Sunday” has everything that would eventually become The Lonely Island’s hallmarks: a simplistic premise, clever rhymes that tell a story about a slightly unusual character, plenty of pop culture references, a catchy, repetitive chorus, and old-school video effects. The jokes might be somewhat dated now, but the sketch as a whole holds up well. Even all these years later, it’s a modern classic.
Could This Be a Movie? It would be a relatively uneventful one… but sure, why not? We’d love to see The Lonely Island attempt a full-length character study.

1) “Mother Lover”
Like Spider-Man 2 before it, “Mother Lover” proves that sometimes the sequel is, indeed, better than the original. Unlike “D**k in a Box” and “3-Way,” it immediately introduces a conflict into the situation (they need a last-minute Mother’s Day present) and reveal some important character backstory about the characters (they were raised by single moms who are lonely, and happen to like baths with chamomile) before reveling in the absurd solution they come up with. They might think it’s the second best idea that they’ve ever had, but thanks to the goofy lyrics, dramatic delivery and the way Susan Sarandon and Patricia Clarkson ham it up in increasingly dumb situations, it’s definitely the best sketch The Lonely Island has ever written.
Could This Be a Movie? We’re ready to buy tickets the second they go on sale. Come on, Timberlake, this could finally make you a movie star. You know you want to make this movie.