the lonely island The Best Lonely Island Videos Ever  

Randolph Strauss
173 votes 41 voters 18.7k views 15 items Embed
A list of the best videos made by The Lonely Island (thelonelyisland on YouTube). The Lonely Island consists of comedians Andy Samberg, Akiva Schaffer, and Jorma Taccone. After making a series of sketches independently and uploading them to YouTube, the group was hired on by Saturday Night Live to write sketches and produce the show's "SNL Digital Shorts" sequences.

This list is ranked by votes, so your votes will help to determine the final order of the videos. Have I forgotten your favorite video? Let us know in the comments!
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I'm On a Boat


Ranker Video
Video: YouTube

First aired: February 7, 2009

Probably the group's most note-perfect send-up of rap cliches and braggadocio, and the fact that the hook is actually being sung by T-Pain doesn't hurt either. "I'm On a Boat" also continues the Lonely Island tradition of videos in which one member of the trio (in this case, Jorma) is purposefully left out of the fun.
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Dick In a Box


First aired: December 16, 2006

Lonely Island had been churning out hilarious parody songs for a few years at this point (including their breakthrough hit, "Lazy Sunday"), but bringing in pop sensation Justin Timberlake turned out to be a true masterstroke. The song - a send-up of cheesy early '90s R&B ballads co-written and performed with Timberlake - became one of the group's biggest hits, and the phrase "dick in a box" genuinely entered the cultural lexicon for a time. Samberg and Timberlake's characters from "Dick in a Box" reunited for the track "Motherlover" with somewhat less fanfare.
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10 3

On the Ground


Ranker Video
Video: YouTube

First aired: October 3, 2009

In this parody of non-conformist hipsterdom, Samberg portrays a poet whose work all deals with refusing things that are offered to him, and instead throwing them on the ground. The video includes guest appearances from actors Ryan Reynolds and Elijah Wood, who react poorly when Samberg's beatnik throws their dinners to the ground. The video ends with the actors assaulting Samberg with a taser.

The video was somewhat poorly received when it originally debuted, but soon enough, the "throw it on the ground" phrase began to pick up some popularity as an Internet meme.
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I Just Had Sex


Ranker Video
Video: YouTube

First aired: December 18, 2010

Andy and Jorma perform a R&B song alongside Akon celebrating in very literal terms the fact that they just had sex with two women, played by actresses Blake Lively and Jessica Alba. Third group member Akiva S******r directed the video and appears in a brief cameo, along with tennis pro John McEnroe. The song is the first single off of Lonely Island's second album, "Turtleneck & Chain."