The Top Ten Lonely Island Songs


So here I’ve compiled the best works by The Lonely Island predating their new soundtrack for Popstar: Never Stop Never Stopping. Enjoy the definitive list of the greatest fake emcees on earth.

Honorable Mention: “We Like Sportz”

This is stupid. But they’re also kind of the best. “We Like Sportz” is the ultimate chapter in the “Just 2 Guyz” saga, which began in 2004, but they’re all well worth watching straight through.

10. “Iran So Far”

First aired on SNL: September 29, 2007

Often forgotten, excluded from Incredibad for an uncleared Aphex Twin sample, “Iran So Far” was one of the best early SNL offerings by the group, and Adam Levine came in for a lovely hook about a lovely dictator.

9. “Spring Break Anthem”

From The Wack Album (2013)

In light of their Macklemore-crushing “Equal Rights,” I’m going to go ahead and call this the real “Same Love.”

8. “Threw It On The Ground”

First aired on SNL: October 3, 2009
From Turtleneck and Chain (2011)

The beat explodes like a landmine hidden beneath the ground Samberg has tossed something upon. This is the perfect send-up of paranoid artists raging against the machine. He threw the rest of the cake, too.

7. “Natalie’s Rap”

First aired on SNL: March 4, 2006
From Incredibad (2009)


So, I guess this is a bit of a stretch, but this gem is on Incredibad. So from a time when we were still thinking about Britney Spears’ shaved head, “Natalie’s Rap” gave us a caricature that was at once unbelievable and totally convincing.

6. “I’m on a Boat”

First aired on SNL: February 7, 2009
From Incredibad (2009)

What can you even say? It feels like a stretch to call this a cutting parody of anything, be it autotune or hip hop materialism. Maybe it’s just bragging about where you’re at. Because damn, I sure wish I was on that boat.

5. “I Just Had Sex”

First aired on SNL: December 18, 2010
From Turtleneck and Chain (2011)

Lots of hip hop is bragging about the tail you get. “I Just Had Sex” puts that in much simpler terms to fantastic effect, and with its singalong chorus and its huge key change, it’s the closest the group skirts to a song you can embrace in all sincerity.

4. “Jack Sparrow

First aired on SNL: May 7, 2011
From Turtleneck and Chain (2011)

Of course there’s Michael Bolton and the excellent premise of a featured hook singer being on an entirely different page, but “Jack Sparrow” also anticipated the Pirates of the Caribbean films’ strange place in history as fun-not-amazing relics of their decade. Of all the films to portray as Bolton’s obsession, it’s an excellent but not at all obvious choice. But the best joke comes about halfway through:

Bolton unexpectedly acquiesces to demands to change it up, and the song is no longer the tale of Captain Jack Sparrow: “Life is a box of chocolates, and my name is Forrest Gump/Though I’m not the sharpest tool in the shed, I give Jenny all my love” sings Bolton as the camera cuts to the familiar bench scene. The first cut is the most surprising and the best, but Bolton’s summaries of his other favorites are just as wonderful, and The Lonely Island surrenders because their club rap anthem and Scarface are close enough.

Okay, I lied. The best part is actually how tickled Bolton is by Jack’s mischievousness: “He’s the pauper of the surf!/The jester of Tortuga!”

3. “Dick in a Box”

First aired on SNL: December 16, 2006
From Incredibad (2009)

“Lazy Sunday” was a smash, but the musical digital short still needed cementing as A Thing. And in came three gifts: 1. Justin Timberlake, 2. Christmas, and 3. a box. The rest is history.

There’s not a whole lot to say here. It’s an R&B pastiche centered around one great joke being told over and over in different ways, so I’ll just leave this here.


2. “Santana DVX”

From Incredibad (2009)

Oh, you haven’t heard of this? It’s just a glorious little rewriting of history where Carlos Santana is dope as E-40, “Smooth” by Santana featuring Rob Thomas of Matchbox 20 was a “music revolution” and not a weird meme standing alongside Smash Mouth, and champagne is marketed not for taste or luxury, but to get you fucked up.

1. “Lazy Sunday”

First aired on SNL: December 17, 2005
From Incredibad (2009)


Though the group had earlier work with “Ka-Blamo!” and “Just 2 Guys,” “Lazy Sunday” was the advent of The Lonely Island, and the group never matched the waves it made online.

Screen Shot 2016-06-03 at 8.39.38 PM

And how could they? It’s the “Nuthin’ But A ‘G’ Thang” of novelty songs. Imagine Weird Al’s “White & Nerdy” wishing so hard he was actually ridin’ dirty and that’s about what we have here. Their braggadocio gives way over and over again to what freaking nerds they are: “I love those cupcakes like McAdams loves Gosling,” “Girl acted like she’s never seen a ten befo’,” and on and on, culminating in their mastery of movie trivia.

NBC was pretty unprepared for this, and many people found sites like YouTube, which benefitted hugely from moments like this, just looking for this viral sensation. But while it played small roles in shaping the net as we know it, “Lazy Sunday” wins for line after line that can stand with the all-time greatest: “You could call us Aaron Burr from the way we’re dropping Hamiltons” remains the best line about the subject despite recent stiff competition.

Joey's a 23-year-old who graduated from the University of Minnesota Morris and now lives in Minnesota's Twin Cities. He enjoys art, activism, and politics, especially when he's looking at them through a lens of popular culture. First and foremost he's obsessed with popular music, but aside from what you'd expect, he's also into comic strips, graphic novels, cartoons, and indie games made for mobile phones (his highest tile in Threes is 3,072). He'll tell you that his favorite book of all time is Goodnight Moon. He needs more people in his life who understand the joys of Achewood.