This digital short, featuring Andy Samberg and Chris Parnell rapping about Red Vines, Mr. Pibb and The Chronicles of Narnia, is the one that put both Samberg and SNL's digital shorts on the map. One could also argue that it's never been topped; though endless parodies, rip-offs and overexposure threatened to ruin the short for a while, you can look at it now and remember just how funny and new it felt. This one clip helped to make Saturday Night Live hip and relevent again. For that, it deserves a great deal of credit.
Though "Lazy Sunday" quickly made Digital Shorts a weekly staple of SNL, it wasn't until four months later that another one really stood out. Not surprisingly, it's another rap (that's where Samberg and the Lonely Island boys, who write and direct the Digital Shorts, really excel). The difference here is that it isn't being performed by a cast member, but rather by guest host Natalie Portman. The contrast of her classy actress image with the vulgar and angry rap she performs is only half the joke; the other half is just how conviningly Portman sells it. She earns cool points forever for this one.
Possibly the only Digital Short that's more popular than "Lazy Sunday," the Christmas-themed "D-ck in a Box" is both one of Saturday Night Live's all-time best holiday sketches and one of the best sketches featuring frequent guest host Justin Timberlake. Though the Digital Shorts seem to be at their best with musical parodies, at least this one isn't a rap song; instead, it's a fairly dead-on spoof of early-90s R&B (think Color Me Badd, if you can actually remember them) that gets a lot of mileage out of that surprise punchline. Even amongst the best Digital Shorts, this one really stands out as a new classic.
As the Digital Shorts became more and more popular, it allowed Andy Samberg, Jorma Taccone and Akiva Schaffer room to become more experimental with their comedy. Thank goodness, too, because without that freedom we might not have gotten the odd-but-great "Body Fuzion" piece, a spoof on early-'80s workout video featuring guest host (and great sport) Drew Barrymore. Besides the silly moves and deadpan expressions (love those close-ups), what really sells the short is the way they've recreated the exact look and feel of an old VHS tape. You know you're onto something when you're getting laughs out of a format.
5. Dear Sister (4/14/07)
I may be in the minority in my love for "Dear Sister," but for me it's one of the funniest Digital Shorts that Saturday Night Live ever put on the air. Though its source could hardly be more obscure -- a scene from an episode of the late FOX teen drama The O.C. -- it's not even necessary to know what it's parodying to find it funny. Using what's arguably my favorite comedy trick -- repeat something until it stops being funny then becomes funny again -- the short just builds and builds, becoming more and more absurd as it goes on. Though the end becomes a little too on-the-nose (always one of the main weakness of the Digital Shorts; they like to spell out the jokes), by then I don't care.
One of the rare "slow burn" Digital Shorts that actually works, "People Getting Punched Just Before Eating" takes a premise that's funny in its simplicity and spins it into unpredictable and fantastic directions. Just when you're tired of seeing people get punched (as if that could ever happen), they start to twist the joke just enough to keep it fresh; by the time Andy Samberg is being chased by zombies through Paris, you know you're seeing something special. Plus, it's got my favorite punchline of any Digital Short ever.
Like "Body Fuzion," this "Japanese Office" Digital Short (featuring guest host and Office star Steve Carell) gets a lot of mileage from subtle observations about the style and structure of the material; it's so much like an episode of The Office, down to the timing and beats, but with just enough changed to make it funny. It's the little touches, like the constant bowing and Kristen Wiig's cartoonish giggling, that put it over the top. In the words of creator Ricky Gervais (who "introduces" the short), "It's funny 'cause it's racist."
"I'm on a Boat" completes the trifecta of Lonely Island's funniest raps. Sure, it's another rap in which they brag about something mundane (that contrast is where a lot of their humor comes from), but what really makes it work is the added twist of having two friends mercilessly mocking a third guy about being on a boat while he's stuck doing something boring. They even have rapper T-Pain with them, just to rub it in.
Timberlake and Andy Samberg tried to recapture their "Dick in a Box" lighting a second time and pretty much succeeded with another classic Digital Short. In this Mother's Day-themed piece, the pair reprise their R&B singer roles in a jam about sleeping with each other's moms (played by Susan Sarandon and Patricia Clarkson). I still contend that it might have been funnier if the moms were women that not everyone wanted to sleep with, but whatever; at this point, Timberlake and Samberg are two for two.
Some of the best Digital Shorts are the ones that take really dark or violent turns (remember the ending to "Cubicle Fight?"), and "The Tizzle Wizzle Show" takes it to the next level by putting that in the context of a happy kids' show. Sometimes, the random absurdist turns taken in the Digital Shorts don't work -- they're odd for the sake of being odd -- but here's an example where each new reveal just makes the piece funnier. You'll never look at a kids' show like Yo Gabba Gabba! the same way again.