Funniest Andy Samberg 'Digital Shorts'

By Tom Ganjamie Posted Sep 27th 2009 09:21AM

If there was one thing that would be certain for the season premiere of 'Saturday Night Live,' it's that resident 'Digital Short' auteur Andy Samberg would have some sort of ridiculously funny video planned. While the Megan Fox-starring 'The Date' and 'Megan's Roommate' were kinda funny (watch 'Date' here and 'Roommate' here), we don't think they lived up to Samberg's past greatness (and really didn't need to be a 'Digital Short'). Now that his first crack at funny is out of the way this year, we figured it was time to put together the all-time most riotous 'Digital Shorts' that Andy's sick brain has ever concocted. Watch them all after the jump!

'Lazy Sunday'

This was the original 'Chronicles of Narnia'-themed Digital Short that set 'SNL' and the viral video world on fire. Lorne Michaels quickly learned that posting the videos Hulu was a way to cash in on them, rather than everyone watching on YouTube.

'D*ck in a Box'

With this video, Justin Timberlake pretty much won over any holdouts left who dared deny his awesomeness. It even led a whole bunch of hyper-relevant people to dress up like the 'D*ck' guys for Halloween 11 months after this 'Digital Short' premiered. Oh yeah, it won an Emmy.

'Laser Cats'

There are now four 'Laser Cats' shorts and hopefully more are on the way. In fact, if Lorne Michaels wants to make 'Laser Cats' in to a full-length feature, it would cost a fifteenth of 'Ladies Man' ... and we'd actually go see it it.

'I'm on a Boat'

Thirty years from now when T-Pain is being inducted in to the Rock N' Roll Hall of Fame (ha!), he better damn will thank Andy Samberg and the Lonely Island guys. Say what you will about auto-tune, it turned this song parody video in to an actual awesome party jam. Take that, Weird Al.

'Space Olympics'

Sure, this probably won't stand the test of time being that it was centered around the Olympics, but this could be the strangest and most nonsensical Samberg venture, and it's also one of our (if not the) top picks.

'Natalie Raps'

Gorgeous, wholesome actress Natalie Portman got down and DIRTY in this short, shedding her image to drop some gross (and hysterical) gangsta rap.

'Jizz in My Pants'

Speaking of gross and hysterical, we sat in amazement the first time this aired, wondering how the heck did Andy slip this one past the censors. Stiff breezes were never this funny, and never will be again.

'Doogie Howser Theme'

'SNL' purists will argue that this not, in fact, a Samberg 'Digital Short,' but he's in it, and it's probably the best non-Sarah Palin thing the show did last year. It's on the list. Deal with it.

'Property of the Queen'

Those of us not in touch with our inner tween girl learned that in another awesome universe, we would easily be fans of The Jonas Brother (As long as they were the 70's rock powerhouse 'Property of the Queen'). Little know fact about The Jonas Brothers: They really do travel with a wizard.

'Roy Rules'

We've heard of Oedipus complex thing, where people are attracted to their mothers, but Andy's sexual fascination with his brother-in-law Roy is just plain freaking strange. And funny. Did we mention funny?

'Iran So Far'

Maybe if Mahmoud Ahmadinejad used this song as his re-election theme and wore a velvet red dress on the campaign trail, there wouldn't have been so many deadly protests in Tehran (too soon?) Either way, this is another musical gem from Samberg's crew, and Adam 'Maroon 5' Levine plays a decent Justin Timberlake.

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Tags: andy samberg, AndySamberg, digital short, DigitalShort, jonas brothers, JonasBrothers, justin timberlake, JustinTimberlake, natalie portman, NataliePortman, saturday night live, SaturdayNightLive, snl, snl digital short, SnlDigitalShort

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