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I'm On a BoatFirst 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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I Just Had SexFirst 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."
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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.)
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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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Like a BossFirst 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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