VOTE The Best Lonely Island Videos Ever  

Randolph Strauss
175 votes 42 voters 18.8k views 15 items

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!
1 17 VOTES

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.
15 2
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2 23 VOTES

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.
18 5
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3 13 VOTES

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.
10 3
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4 15 VOTES

Like a Boss

Ranker Video
Video: YouTube

First aired: April 4, 2009

One of the few Lonely Island songs that's a direct parody of a single song, "Like a Boss" is a take-off of a Slim Thug song by the same name. (Samberg based some of his descriptions of office life in the song on his own pre-SNL work experiences.) The clip is also one of the more "edgy" of the Lonely Island videos, and had to be rather extensively edited for television (including bleeping out the word "dick" and removing some of the more overt references to suicide.) Seth Rogen guest stars as Samberg's supervisor.

In addition to just being really funny and rewatchable, the video also helped introduce the phrase "like a boss" into common Internet jargon.
11 4
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