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The Best Lonely Island Videos Ever

A list of the best videos made by The Lonely Island (thelonelyisland on YouTube). The Lonely Island consists of comedians Andy Samberg, Akiva S******r 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 voteranked, 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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  1. 1
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    I'm On a Boat


    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.

  2. 2
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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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    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").

  4. 4
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    Like a Boss


    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.

  5. 5
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    On the Ground


    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.

  6. 6
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    Natalie's Rap


    First aired: March 4, 2006

    Actress Natalie Portman hosted SNL as part of the promotion for the film "V for Vendetta." Included in the show was this SNL Digital Short, a fake "interview" between Portman and Chris Parnell that unexpectedly turns into a fake rap confession about the actresses misdeeds. (For example, claiming to have cheated her way through Harvard University and having a variety of drug addictions.) The sketch also features cast member Seth Meyers, whom Portman assaults during the course of the song. Portman has also appeared in a fake interview for the Internet series "Between Two Ferns with Zach Galifianakis."

  7. 7
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    Iran So Far

    First aired: September 29, 2007

    Samberg performs a love song for Iranian president Mahmoud Ahmadinejad (played by Fred Armisen) with some help from Maroon 5's Adam Levine. A surprise appearance from actor Jake Gyllenhaal rounds out the cast, which plays with Ahmadinejad's much-discussed homophobic comments from the time. (TRIVIA: The song samples "Avril 14th" by Aphex Twin.)

  8. 8
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    - 3

    Shy Ronnie

    First aired: December 5, 2009

    Special guest star Rihanna performs a duet for a classroom of children with Andy Samberg in this parody of R&B artists featuring on one another's songs. The sketch proved popular enough to warrant a sequel, entitled "Bonnie and Clyde," where Rihanna once again appears alongside Shy Ronnie. In both cases, he's unable to perform with Rihanna in the room.

  9. 9
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    - 0

    Just 2 Guyz


    First aired: December 23, 2005 (YouTube)

    The video for "Just 2 Guyz" pre-dates Lonely Island's involvement on "SNL." It's a brief song performed by Jorma and Akiva praising themselves for their everyday awesomeness. (Once again, part of the joke is the purposeful exclusion of one group member, in this case, Samberg as the character "Steve.")

    The 2 Guyz would return in similar fashion in a later Lonely Island video called "We Like Sportz."

  10. 10
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    I Just Had Sex


    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."

  11. 11
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    Jizz In My Pants


    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."

  12. 12
    + 1
    - 1

    Jack Sparrow


    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."

  13. 13
    + 0
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    The Curse

    First aired: January 30, 2010

    This sketch parodies the Sam Raimi film "Drag Me to hell." Andy Samberg plays a businessman cursed by a gypsy (Fred Armisen), who is doomed to be shadowed by mysterious, sexy sax player Sergio (portrayed by "Mad Men's" Jon Hamm.) According to Wikipedia, Sergio was inspired by musician Timmy Cappello from the film "The Lost Boys."

    The video is thought to have inspired more "sexy sax man" YouTube videos, like this one:

  14. 14
    + 2
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    People Getting Punched Right Before Eating


    First aired: October 13, 2007

    One of only 2 entries on this list that ISN'T a song parody, this dialogue-free skit features a gleeful Andy Samberg running around New York punching people in the face right as they are about to take a bite of food. His victims include both SNL cast members Will Forte, Fred Armisen and Jason Sudeikis, but also that week's guest host, Jon Bon Jovi, and multiple members of musical act The Foo Fighters. The sketch also features one of the group's more surreal, non sequitur endings.

  15. 15
    + 1
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    Ras Trent


    First aired: October 25, 2008

    JAH! Andy Samberg parodies white suburban undergrads who discover Rastafarianism while away at college in this faux-reggae video. The song includes a number of mispronounced Jamaican words and phrases, as well as obscure references to a variety of other reggae songs.

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