The 5 Greatest Lonely Island Digital Shorts

In celebration of this weekend’s release of Popstar: Never Stop Never Stopping, I thought it would do us all a little good to look back on the career that got The Lonely Island to the point that they got to make a feature film and remind you how fucking funny Andy Samberg, Jorma Taccone, and Akiva Schaffer are.

5) Jack Sparrow

Starting with a song feels only appropriate. However, given the wealth of hilarity that their music has brought us, it’s hard to pick. But Jack Sparrow embodies pretty much everything I love about them as parody artists.

Their parody is a legitimately catchy and well-made tune. Until Bolton breaks in at the chorus, it’s hard to distinguish this from an actual club hit. Of course, that break-in, that Michael Bolton has written his hook about movies he’s been watching, is just such a hilarious and specific idea that doesn’t get less funny on repeat listens. These guys know what they’re parodying and they know how to put just the right spin on it.

Plus, when they use celebrities, it doesn’t just feel like a game. Bolton’s use here actually feels like you’re learning some new part of him, and that’s what makes this song as much as fun as it is.

4) The Curse

Watch it here

This one gets a million points for just sheer audacity. I don’t actually want to give this one away too much if you haven’t seen it, but the final iteration of the joke (Jon Hamm’s repeated appearance as Sexy Sax Man Sergio) is one of the most gut-bustingly funny images I’ve ever seen no matter how many times I’ve watched this sketch. Seriously, I’m giggling while I’m writing this and it’s not even playing.

3) Seducing Women Through Chess

Probably my most left-field choice, but this one really hits my funny bone. Partially, it’s the debt these guys owe to, and also helped carve out in, alternative comedy of the deliberately shitty VHS aesthetic that just adds a layer of ridiculousness, and the budget SNL gave them lets this one look like a legitimately spot-on parody of a lost 80s bizarre artifact.

Plus, Samberg is never better than when he’s playing pathetic and this is full-on one of his most pathetic characters and most hilarious performances. He wears sad and desperate in every bit of this character and it’s comedy perfection.

It’s an example of the dead-on stupid character work that Lonely Island could do at their best (and the kind of skill that ends up making Popstar as good as it is).

2) The Shooting

Holy shit guys. Let me say that choosing between #2 and #1 was incredibly difficult and this may be my favorite on any other day.

It’s just comedy gold. A parody of something no one remembers (the second season finale of The O.C.) that still stands up perfectly on its own. Plus, legitimately smart filmmaking, holding those reactions and cutting the song in a way that absolutely nails every comedy beat.

Plus, it escalates perfectly. I don’t know if I can explain it in a way that conveys it better than just watching it, but by the ending, this one has ascended into the sketch comedy classics. It’s a perfect combination of performance and comedy filmmaking.

In fact, it would be the best if it wasn’t for…


1) Motherlover

If The Lonely Island have a masterpiece, it’s this. Literally everything they do comes together.

Pitch-perfect parody. Not only is this a legitimately crazy catchy song with a sick beat, but it actually has a grounding in something these guys grew up with and know very well. It’s so specific and weird that it doesn’t feel out of place.

Sheer audacity. It’s a song about two bros who agree to “fuck each other’s moms” for Mother’s Day. Just a bananas concept the two play perfectly straight.

Great character work. That line Justin Timberlake sings to himself saying “We are so cool and thoughtful” is just genius.

Most importantly, it’s just breathtakingly funny. Years of comedy work came together and it resulted in Motherlover, the best Lonely Island sketch.