The Lonely Island: Saluting 15 of Their Finest Moments

Andy Samberg, Akiva Schaffer and Jorma Taccone are comedy trio The Lonely Island. Here are just some of their finest songs and sketches...

This story originally ran on Den of Geek UK.

Popstar: Never Stop Never Stopping was – yep, it’s time to call it – the funniest film of 2016. For those who blinked a little too long and didn’t catch it on its brief appearance in cinemas, the DVD release is your chance to find out what you’ve missed: a hilarious parody of current pop music’s excesses that blends acerbic criticism of predatory gossip shows and social media mobs with a sweet story of three feuding rappers struggling to mend their friendship. The fact that this touching tale also features Seal fending off a pack of wolves, Justin Timberlake dressed as a fish, and a bagpiper playing a lament at a beloved pet turtle’s Viking-inspired funeral comes as no surprise to anyone even vaguely familiar with its three stars. Andy Samberg, Akiva Schaffer, and Jorma Taccone are The Lonely Island, and Popstar – like their previous film, 2007’s cult classic Hot Rod – is a movie nobody else could have made. 

You’ll recognize Samberg from Brooklyn Nine-Nine or HBO’s tennis mockumentary, 7 Days In Hell. It’s a safe bet that you’ll also have seen at least one of the Dudes’ viral hits: “Like A Boss,” perhaps, or the ubiquitous “Lazy Sunday.” With three albums’ worth of spot-on musical send-ups and two brilliant movies behind them, the abundantly talented trio somehow aren’t often given the credit they deserve. Maybe it’s to be expected, though; ground-breaking comedy tends to get a bafflingly poor reception at first (just ask Steve Martin and Jim Carrey). And comedy, frankly, doesn’t get more innovative than this. Here are a few of their finest moments.


The three friends met at high school in Berkeley, California and stayed in touch while studying at different colleges, before moving to Los Angeles together in 2000 to pursue careers in film. While paying the rent with various part-time jobs, they spent their evenings putting together comic rap videos. In September that year, “Ka-Blamo!” was the first of their efforts to appear online. Hilarious, memorable and wonderfully weird, it set the bar high. Never turn your back on a mole while coal mining, kids.

Ad – content continues below

Stork Patrol

While we’re on the subject of animals doing things they shouldn’t, here’s 2002’s “Stork Patrol,” in which the Dudes all fall passionately in love with a seductive stork. If Ovid had been a fake rapper in the twenty-first century, this is how the Metamorphoses would have turned out. Am I right, classicists?

The Lonely Island Sitcom

This was The Lonely Island’s first attempt at a sitcom format before The ‘Bu, and the self-titled show’s episodes (“White Power” from December 2001, and “Regarding Ardy” from February 2003) are both fantastic. Two celebrity guest appearances are worth noting. One is, incredibly, an unplanned cameo from Kiefer Sutherland in full Jack Bauer mode when he mistook one scene’s fake beating for a real mugging as he drove by. The other is by Brooke Shields, who introduces the second episode with the story of how her collaboration with the trio ended with her conceiving a

LonelyIsland baby. This, somewhat unexpectedly, is the perfect way to begin a mash-up of “Regarding Henry” and “Born on the Fourth of July.”

The ‘Bu

From 2003 to 2005, The ‘Bu was screened as part of Dan Harmon and Rob Schrab’s short film festival, Channel 101. Over eight instalments – the last of which takes the form of a musical apology for the lack of an episode that month – we follow the bizarrely compelling story of Malibu-based ninja, Brett (Taccone) and his attempts to romance glamorous Melissa (played variously by ScrubsSarah Chalke, long-time Lonely Island collaborator Chester Tam, and a blonde-wigged dummy) while avenging his murdered brother and fighting off romantic competition from hot-headed Aaron (Samberg). That description only makes it sound about half as fantastic as it actually is. This parody of The O.C. was so popular that even when The Lonely Island moved on to make Awesometown, it took three further episodes and the best efforts of several other people to get it “cancelled” by the festival’s voters. Here’s comedy writer Jeff Loveness on its lasting influence.


This pilot for a series was never aired by Fox as intended, but is full of promise. It would have fitted in perfectly with British TV comedy of that time, as fans of The Mighty Boosh and Garth Marenghi’s Darkplace will agree. Not long after this, the trio were hired to write for the 2005 MTV Movie Awards; in August that year, they were taken on by Saturday Night Live, with Samberg as a featured player and Schaffer and Taccone as writers.

Lazy Sunday

In December 2005, The Lonely Island had an overnight success with “Lazy Sunday,” in which Samberg and Chris Parnell prowl New York’s snow-covered streets on a rap-driven quest to see The Chronicles of Narnia: The Lion, the Witch and the Wardrobe. One of YouTube’s first viral hits, the video immediately raised their profile, got them a record deal, and saw them put in charge of the SNL Digital Shorts, which became a staple of the show. This tenth-anniversary oral history of its creation explains how Lazy Sunday came about. 


Laser Cats

A send-up of The Lonely Island’s attempts to pitch ideas to SNL producer, Lorne Michaels, Laser Cats’ seven episodes chart the low-budget adventures of Admiral Spaceship (Samberg) and Nitro (Bill Hader) as they battle a succession of villains with the assistance of a host of celebrity guests. There’s an element of Hot Rod in space with this, which is really all anyone could ask for. 

Ad – content continues below

I’m on a Boat 

Another huge hit, “I’m on a Boat” sees the Dudes joined by T-Pain as they eulogise the simple pleasures of being on a very big, very expensive boat while everyone else is stuck doing mundane, land-based things. This affectionate jab at hip-hop’s more excessive moments appeared on their first album, 2009’s Incredibad, along with the brilliant “Jizz in My Pants” and the vision of corporate nightmares that is “Like A Boss.” Other standouts include a tongue-in-cheek ode to celebrity champagne in Santana DVX (‘As a kid, I used to lie awake and think/When was Santana gonna make a drink?’) and the peerless Space Olympics, in which we learn that no amount of interstellar grandeur can overcome bureaucratic cock-ups.

Cool Guys Don’t Look At Explosions 

“Keyboard solo, J.J. Abrams!” Not words we ever expected to hear, but then he did write the theme for Fringe, amongst others… Cool Guys Don’t Look At Explosions was made for the Samberg-hosted 2009 MTV Movie Awards, hence the cameos from Abrams and Will Ferrell playing a sparkly-suited Neil Diamond as The Lonely Island ruin all action films forever, in the best possible way.  

Threw It On The Ground 

Hipster petulance is skewered in this track from the trio’s fantastic second album, Turtleneck and Chain (2011). Samberg’s marvellously hateful character throws everything he can find on the floor, whether it be a free hot dog, a child’s birthday cake or his girlfriend’s mobile (‘Man, this ain’t my dad! This is a cell phone!’). His rage against “the system” that’s supposedly oppressing him is brought to a grim end by a taser-wielding Ryan Reynolds and Elijah Wood after their dinner ends up… well, you guessed it.  

Jack Sparrow 

Michael Bolton’s Pirates of the Caribbean-referencing collaboration with The Lonely Island is a thing of such brilliance that it probably deserves its own feature. Bolton’s reluctance to sing the lyrics he was originally given led to repeated rewrites, apparently, but the finished product lets the singer have a great joke at his own expense and come out of it all looking very cool indeed. Well played, sir – and much credit to the trio themselves, whose ability to provide a safety net for the celebrities guesting on tracks like this only adds to the fun.

Great Day 

Samberg’s cocaine-addicted businessman explains the supposed benefits of his lifestyle by means of a jaunty show tune in this track, which somehow manages to be both utterly hilarious and rather sad.

3-Way (The Golden Rule)

“Dick in a Box” might be the most famous of the trio’s collaborations with Justin Timberlake, and Motherlover might be the weirdest (all right, that’s open to debate) but 3-Way – featuring Lady Gaga as the woman determined to bed both the lecherous R&B singers played by Samberg and Timberlake – is the logical conclusion to the dodgy duo’s questionable dating recommendations.


The lead single from 2013’s The Wack Album subverts that year’s ubiquitous slogan by reminding us that the letters in the annoying acronym can also stand for “You Oughta Look Out.” Household objects take on deadly significance as Kendrick Lamar turns up to offer sensible financial advice to today’s youth, with an addictive sample of Welsh rockers The Joy Formidable’s Whirring’ thrown in for good measure. The video’s premiere on SNL was the trio’s first appearance on the show since Samberg and Taccone’s departure in 2012 (Schaffer had left in 2010). Great stuff, although their paean to punctuation, Semicolon, is still the best track on the album, obviously.  

Ad – content continues below

Everything Is Awesome 

The LEGO Movie’s joyous sugar-rush theme, “Everything Is Awesome,” was provided by The Lonely Island and Canadian duo Tegan and Sara. That movie was largely neglected at the 2015 Oscars, but it did get a Best Song nomination, and the performance on the night was a highlight. A guest appearance by Lego Batman himself (Will Arnett) and backing from Questlove and Devo’s Mark Mothersbaugh provided the icing on the cake. The song may not have won, but the audience certainly did.

Join Amazon Prime – Start Free Trial Now

And that brings us to now. We’ve got Michael Bolton’s Valentine’s special on Netflix to look forward to – featuring The Lonely Island and directed by Schaffer – along with MacGruber 2, currently being written by Taccone and Will Forte, and Samberg’s upcoming send-up of doping scandals in the cycling world, “Tour de Pharmacy.” Long may the Dudes reign – and whatever they come up with next, it’ll definitely be ka-blamo.