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The 10 Funniest Lonely Island Videos

The 10 Funniest Lonely Island Videos

The 10 Funniest Lonely Island Videos
Danielle de Wolfe
30 December 2015

Dear Lonely Island,

We think we speak for the entirety of the United Kingdom when we say "thanks for the memories."

Hang on. That makes it sound like they're splitting up, which they're absolutely not. It's just that it only recently occurred to us that it's twelve years since they exploded onto the Saturday Night Live scene and, to our eternal shame, we're yet to compile our top 10 musical shorts from the insanely funny, horribly talented comedy group. 

So we've rectified that, below. 

Go Kindergarten

Featuring: Robyn, Paul Rudd, Puff Daddy/Diddy/Puffy/Sean Combs/that guy

Ludicrous scenes as the Puffy one and Rudd find themselves in a music video where the hook is supplied by Swedish pop queen Robyn. Laughs crescendo to the point where the demanding lyrics insist the ladies whip their dicks out: "Don't ask how, just fuckin' figure it out." By the time Combs is delivering Robyn's baby, we're in crack-a-rib-laughing-and-not-even-care territory. Glorious. 

I'm On A Boat

Featuring: T-Pain

The trio had met T-Pain when he guested on Saturday Night Live a year prior to filming this hip-hop excess parody that has, even in Lonely Island terms, lashings of profanity. T-Pain told them he was a big fan of Hot Rod and, soon enough, he was shooting the vid "on a boat, motherfucker, don't you ever forget." The track reached number one on YouTube in February 2009 (it's had well over 110 million views) and was number one on the U.S. iTunes music video chart. It was nominated for Best Rap/Sung Collaboration at the 52nd Grammy Awards and went double platinum.

Cool Guys Don't Look At Explosions

Featuring: Will Ferrell, JJ Abrams

Why not turn this video into a quiz? That'll be fun, right? Give it a watch and try and list as many of the 18 movies from which explosion scenes are borrowed. Then, head right this way where we reveal the answers!

You're not going to do that, are you? Not a single one of you. Very well. Enjoy the video. 

Threw It On The Ground

Featuring: Elijah Wood, Ryan Reynolds

If ever proof were need that calling a young lad "a poser" while hurling his birthday cake to the floor is funny, it's here. This is pure, unadulterated Samberg as a Generation-X style anti-establishment hipster who won't take free hot dogs, free energy drinks or phone calls from his father. Bonus points for a goatee you could set your watch to. 

Spring Break Anthem

Featuring: James Franco, Zach Galifianakis, Edward Norton

Of course Wikipedia isn't a place for fun and games, but they're description of Spring Break Anthem is just brilliant in its dryness: "The song satirizes American spring break culture," they say "Which is illustrated as uproarious and irresponsible, juxtaposing it with the concept of same-sex marriage."

Yep, that pretty much covers it. 


Featuring: Julian Casablancas

Ever seen a Spanish guy doing the Bartman? Here you will, as well as unhealthy volumes of boiled goose and a precautionary tale about knowing your limits with a boombox. The Strokes' singer, Julian Casablancas, actually said this was the most fun he's ever had working in music. Stopped short of calling it the most fun he's ever had, of course. Now that would be a story worth hearing. 

I Just Had Sex

Featuring: Akon, Jessica Alba, Blake Lively and John McEnroe

Ready for a mildly interesting fact about this video? The building on which the band are stood, with the Empire State backdrop, is the MetLife building which is used for Stark Tower in The Avengers movie. Stark Tower looks rather different but James Chinlund, the production designer on the film, explains: "Tony Stark bought the iconic MetLife Building (formerly the PanAm Building) and ripped off the top adding his own piece of parasitic architecture. The height of arrogance and the essence of Stark." So there you have it, if Tony Stark weren't fictional, Lonely Island would have had to find a different building. And we're boring ourselves writing this. 


Featuring: Justin Timberlake, Patricia Clarkson and Susan Sarandon

A brilliantly awkward number that sees Samberg and Timberlake setting each other up with their respective mums, and Susan Sarandon caressing JT. Apparently it was made during a sleepless week of writing, recording and shooting before it was due to air. Samberg and Timberlake recorded the song in an all-night session two days after it was written, with a 20-hour video shoot commencing the following day. Schaffer began editing the footage early Saturday morning and only completed the short within minutes of its broadcast debut, finalising the video while the show was already live.

Jack Sparrow

Featuring: Michael Bolton

You've got to love the message Michael Bolton posted on his website shortly after shooting finished for this global, viral sensation: "Working... on the Jack Sparrow digital short was one of the highlights of my career and most memorable experiences of my life... They made me do things I never would have expected to be comfortable with and I'm so glad I did. Truly grateful to be a part of this project and CANNOT WAIT for the chance to work with the guys again. Now Back To The Good Part." 

One of "the most memorable experiences" of his life, says the father of three, eight top 10 albums and two number one singles superstar who's bagged multiple American Music Awards and Grammy Awards. Brilliant stuff. 


Featuring: Adam Levine, Kendrick Lamar, Danny McBride

Redefining Drake's risk-taking mantra to mean its opposite "You Oughta Look Out" this one was originally set to feature Katy Perry, but two weeks before the song was released, they bought in Maroon 5's Adam Levine, who was hosting Saturday Night Live the night the short would air. Our lyrical highlight?"Don't travel by plane, don't travel at all / build a bomb shelter basement with titanium walls."

How good was this song? Well, Rolling Stone named YOLO one of the 100 best tracks of 2013.