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The 16 Funniest SNL Digital Shorts in Show History  

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1.2k votes 309 voters 21.4k views 16 items

Saturday Night Live is one of the longest running television programs in TV history. In the early 2000s though they started doing something a little bit different though. SNL brought on a comedy troupe called The Lonely Island (Andy Samberg, Jorma Taccone and Akiva Schaffer). The trio was best known for their comedy based web shorts and music videos so it was no surprise that this was exactly what they started to produce for Saturday Night Live and thus the SNL Digital Shorts were born. 

The first major Digital Short was called "Lazy Sunday" which featured Samberg and Chris Parnell rapping about going to see a movie. This video blew up huge on the Internet and SNL wisely started making the Digital Shorts a main stay. Since then there have been some amazing music videos and sketches born from the SNL Digital Shorts. This list compiles those hits and asks the question, "What is the best SNL Digital Short"?

Vote for your favorite SNL Digital Shorts below, from Dick in a Box to Like a Boss.  

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1 222 VOTES
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Video: YouTube

A Christmas song about two men (Justin Timberlake and Samberg) giving their lovers (Kristen Wiig and Maya Rudolph) a box with their genitalia inside as presents, in a style reminiscent of early 1990s R sex ballads made popular by acts such as Bel Biv Devoe, Color Me Badd, and R. Kelly. Won a 2007 Creative Arts Primetime Emmy for Outstanding Music and Lyrics. Music created in part by Asa Taccone, Jorma Taccone and Katreese Barnes. It was the first official single from The Lonely Island's debut album, Incredibad. ...more on Wikipedia

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see more on SNL Digital Shorts: Dick in a Box
2 109 VOTES
I'm On A Boat (ft. T-Pain)
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Video: YouTube

From The Lonely Island's album Incredibad. Samberg wins a prize from a cereal for a boat trip for three and selects himself, Akiva Schaffer and surprisingly, T-Pain while Jorma Taccone stays out of the excitement. Then the group proceeds into a highly aggressive, profane rap song about sailing on a boat, including 18 uses of the word "fuck". The second single from the Lonely Island's debut album 'Incredibad'. ...more on Wikipedia

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3 114 VOTES
Lazy Sunday
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Video: YouTube

Chris Parnell and Samberg rhyme about The Chronicles of Narnia: The Lion, the Witch and the Wardrobe, cupcakes, Mr. Pibb, Red Vines, Matthew Perry, and a host of other products. The short became a viral video online. Music produced by Jorma Taccone. ...more on Wikipedia

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4 110 VOTES
Natalie Raps
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Video: YouTube
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