Today is Andy Samberg’s 36th birthday, so let’s celebrate the occasion by taking a comprehensive look back at some of his best digital shorts on Saturday Night Live. During Samberg’s eight-year run on SNL, the shorts became one of the biggest reasons to tune in every week, and this guide to the 20 strongest segments will remind you why.
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Lazy Sunday
The one that started it all, and in the eight and a half years since it first aired, it’s become legend. It was also the way that many people were introduced to YouTube. Need we say more?
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Natalie Portman’s Rap
If you were like me, the crush you already had on Natalie Portman increased significantly after seeing this one. Plus, her line about wanting to punch Jeff Zucker in the face rings true for all of us.
https://www.hulu.com/watch/1402
D— In A Box
Motherlover
3-Way (The Golden Rule)
Every digital short that Timberlake was involved in was brilliant. I tend to be partial to “D— In A Box,” because it came first (heh), and it’s just freaking hilarious. But “Motherlover,” and “3-Way (The Golden Rule)” are fantastic in their own right. Really, you can’t go wrong with JT.
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People Getting Punched Before Eating
A fine example of how a relatively simple idea can be made hilarious through right combination of electronic music and Andy Samberg dancing. Plus, as a Buffalo resident, the part where he punches Bon Jovi has become quite cathartic.
Dear Sister
A brilliant parody of an episode of The O.C. that features some gratuitous violence. Also, this sketch features easily the best use of Imogen Heap’s “Hide And Seek.” Sorry, Jason Derulo.
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Iran So Far
Easily the best thing Adam Levine has ever done — although his other appearance on this list comes close. Sadly, this track did not appear on The Lonely island’s first studio album, even though it’s one of their absolute best. The problem might have stemmed from difficulty clearing the sample of Aphex Twin’s “Avril 14th.” In any case, Samberg’s ode to Mahmoud Ahmadinejad, who is “like a very hairy Jake Gyllenhaal” will live on in our hearts.
Ras Trent
This one isn’t quite as popular as some of the others on this list, but it’s hilarious nonetheless. Anyone who has ever dealt with an insufferable trust fund kid who just found that reggae music exists can relate. The best part is all the words he just learned flashing across the screen. Or the part where he walks past a bunch of black dudes and starts singing considerably more quietly. Or the random Murder, She Wrote reference.
I’m On A Boat
An undeniable classic – and the first time The Lonely Island had a flat-out pop hit. A few weeks ago my friend and I were arguing over the last time T-Pain was relevant. His response? “What year did ‘I’m On A Boat’ come out?” It was 2009, if you were wondering.
J— In My Pants
Well, this one is a bit graphic to say the least. Apparently, even eating a grape causes or narrator to…well, you know. Samberg’s fake British accent is the secret MVP of this song.
Like A Boss
Much like “I’m On A Boat,” this one launched a catchphrase that still gets thrown around today. more importantly, it discussed the more mundane — and even painful — aspects of being a boss.
I Just Had Sex
Another bonafide pop hit, and by the far the highlight of Akon’s career (a lot of otherwise dubious performers did their best work with The Lonely Island). This song reminded us that if you had sex, that means you had sex. Even if she’s a racist, or she made you wear a bag over your head.
I Threw It On The Ground
For all the rebels who have no idea what they’re supposed to rebel against. Samberg’s narrator throws everything on the ground, for increasingly questionable reasons (“That’s not my dad. THAT’S A CELLPHONE!”), and in the end, he gets what’s coming to him.
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Shy Ronnie 1 And 2
Well, Rihanna can be a bit intimidating, but we’re guessing Ronnie would be just as shy no matter who he was performing with.
Jack Sparrow
Making Michael Bolton cool is a Herculean task, but damned if The Lonely Island weren’t able to pull it off. Hearing the man behind “How Am I Supposed To Live Without You,” and “Can I Touch You….There?” sing “this whole town is a p—y just waiting to get f—ed” is a lifetime highlight to be sure.
Spring Break Anthem
A solid mockery of the bro-down culture of spring break, where Samberg raps about “jokes about roofies” and “trading beads for their bras,” but really he just wants to marry a dude. And since the dude in the video is James Franco, you can hardly blame him.
YOLO
In early 2013, we had all grow sick and tired of the phrase “YOLO,” so leave it to the Lonely Island to miraculously find a way a way to make it funny — with some help from Kendrick Lamar and Adam Levine. In this sketch, they invert its original meaning turning into a reminder to stay safe. As they point out, YOLO could also stand for You Oughta Look Out.
When Will The Bass Drop
As succinct of a takedown of Dubstep as you’re going to find. Samberg’s DJ is given bags full of money and is praised as “the king” when all he does is tease the audience by not dropping the bass! Plus, we get a funny cameo from Lil Jon, fresh off the success of “Turn Down For What.”
