The Best Lonely Island Videos Ever

By 173 votes 41 voters 18k views 15 items tags f p @
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

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    Photo: 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.
  3. 3
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    On the Ground

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    Photo: 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

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    Photo: 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."
  5. 5
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    Like a Boss

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    Photo: 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.
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    Jizz In My Pants

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    Photo: YouTube
    First aired: December 6, 2008

    Another parody of R&B videos features the Lonely Island trio singing about extreme problems with premature e*********n. Cameo appearances in the video feature Molly Sims, Jamie-Lynn Sigler and, once more, Justin Timberlake. As with some of the more adult Lonely Island videos, separate censored and uncensored versions were released on the Internet after the video was released. This was the first single from The Lonely Island's first album, "Incredibad."
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    Jack Sparrow

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    Photo: YouTube
    First aired: May 7, 2011

    Singer Michael Bolton guest stars on another hip-hop parody from the Lonely Island guys. While the comedy trio raps about going to the club and other traditional topics for such songs, Bolton sings the hook exclusively about Captain Jack Sparrow from the "Pirates of the Caribbean" film series. As the song continues, Bolton weaves in even more film references, including nods to Forrest Gump, Erin Brockovich and Tony Montana.

    Bolton has called the short film "one of the highlights of my career and most memorable experiences of my life."
  8. 8
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    Lazy Sunday



    First aired: December 17, 2005

    "Lazy Sunday" was the second-ever SNL Digital Short produced by Lonely Island, and one of the first SNL sketches in which Andy Samberg appeared. (The clip features Samberg and Chris Parnell performing what sounds like a hardcore rap song that really just references a pleasant day spent eating cupcakes and watching "The Lion, the Witch and the Wardrobe.")

    "Lazy Sunday" was one of the first big YouTube viral sensations, and spawned thousands of parodies (including one called "Lazy Scranton" on the NBC series "The Office").
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