The (CHRONIC, WHAT?!) Top 8-ish SNL Digital Shorts

In 2001, a Trio of Young comics teamed up to create a series of short films for the always budding Los Angeles alternative comedy scene; After showing their films at various clubs/performance houses, This trio would eventually catch the attention of a prolific comedy icon. That icon’s name…………was actually Dan Harmon, who’s cult classic website “Channel 101” took a chance on the trio, and a few years later they were able to come up with material that eventually caught the attention of Another prolific comedy icon……after Jimmy Fallon recommended them to his (then) former boss. Long story short, Akiva Schaffer, Jorma Taccone, and a young mop-top named Andy Samberg brought their “Lonely Island” to the shores of 30 Rock to create one of the show’s most durable Franchises within the Franchise; the SNL Digital Shorts. To say how important these shorts were to SNL, Comedy history and Streaming Media is as much expansive as it is redundant; but praise must be heaped on them anyway—for without the Digital Shorts, the show would’ve remained a lumbering dinosaur with little to no relevance (except in election years, of course), and the show would not be worth watching today if the work of the island didn’t help pave the way for people like “Matt & Oz” to carry the torch after Samberg & Co. left in 2012. SNL owes a Lot to Samberg’s crew, and we are here to take a look at the moments that were as much memorable as they were sometimes strange.


There is no Criteria per se—as long as the short itself has the words “An SNL Digital Short” on the front of it, it’s eligible. At the same time, I feel the need to stress more than ever that this is in MY Opinion Only, partly because there are Far, Far, FAR too many lists out there that that rank the digital shorts. One list in particular has the arduous task of ranking every last one of them; which is all fine and good, but I’m speaking strictly as a fan, not as an analyst. That being said, I do feel the need to make the following painful exclusions:


*“Lasercats”; technically this is a “Recurring” bit; and at the same time, they all follow the same plot, so why be redundant 7 times?


 *“The 100th SNL Digital Short”, because I really see that piece as more of a “Palate Cleanser”—just about every single one of the shorts are called back, and it wouldn’t make sense to talk about a “compilation” when I’m about to make a list that is in itself a compilation.

*“That’s When you Break” from the 40th Anniversary show—sort of goes without saying because the short appeared on a Prime Time Special; around here, we focus on the “Show Proper”. Or to loosely paraphrase Lorne Michaels, It goes on the list because it goes on at 11:30



And of course, we need to take a moment to address two very large digital elephants in the room before we get started…



LAZY SUNDAY (12/15/2005) & DICK IN A BOX (12/16/2006) – I can honestly say without hyperbole that these pieces are probably two of the most iconic sketches to have appeared on the show in all the years it’s been on the air—if not, somewhere in the top 10. At the same time, the more iconic you are, the more overrated you run the danger of becoming in later years (Just ask Pete Schweddy and the Festrunk Brothers if you doubt the claim). My hair would’ve fallen out if I had to figure out which of these two is the better short, because I didn’t want to have my #1 pick end in a tie. So in the interest of fairness (ESPECIALLY considering there are over 100 shorts to look through), I hope you can forgive me if “Dick” and “Lazy” stay as FAR away from this list as possible. If you want to know what my opinion is on “Dick” (and yes, I know that came out wrong), take another look at #6 on my “Original Songs” list. As for “Lazy”; it’s the sketch that Turned Youtube into a commodity and an annuity at the same time, its place in history is very well secured; and I’m all but certain that both will stand the test of time for years to come—if there was a number higher than one, both of them would be in that position; but because both of these shorts deserve the top spot more than anything else, I hope you can forgive me for counting down from 8 to 2 this week. Further, I would put “Jizz in my Pants” and “I Just had Sex” in the same category because all of these shorts aired around Christmas time; a time where they knew a lot of younger people would be watching, so of course all 4 of these pieces would go viral.



Now that we got that out of the way, let’s look at the rest of the best…




8. HARPOON MAN (10/21/2006) – Because of how influential the aforementioned shorts are, it’s pretty easy to forget that some of the Digital Shorts weren’t exactly a “hit” out of the box (as some “Honorables” will point out)–sometimes you had to eat some bizarre vegetables before you get to dessert. Case in point, John C. Reilly plays the title character as he hunts his prey on the mean streets of Manhattan—while at the same time, Samberg “sing-raps” about Reilly’s exploits and his flaws. Then Samberg’s focus on the flaws cut a little deeper, until ultimately Reilly tracks down Samberg and…well, c’mon, the name of the short is “Harpoon Man”, what else is gonna happen? This actually reminded me of a Film Gary Weis did in 1978 with Larraine Newman that was almost the same concept—tracking down an annoying, off-screen singer (which I can’t show you because neither video nor transcript exists—but if you have the Season 3 DVDs, look up Chevy Chase’s episode), but trust me when I say the comparisons are there.



7. LIKE A BOSS (4/4/2009) – You know something is gonna last forever when a certain phrase winds up appearing everywhere…and I mean EVERYWHERE. And while “Lazy” & “Dick” has seen its fair share of marketability when they first aired; The phrase “Like a Boss” has become so entrenched in the American vocabulary, that it doesn’t surprise me to see those words printed on T-Shirts, internet memes, and other means of mass commercialism. So, why so low on the list if the short’s impact is patently strong? Well, aside from hardcore selling out, this film suffers a little from a slight case of what I like to call “Kaufmanism”—this is that strange phenomenon where a joke or a line is told, then that same joke/line gets told over & over again to the point where it’s no longer funny, but then is told several times more so that the material is funny all over again; not unlike anything Andy Kaufman ever did (hence: “Kaufmanism”). On the plus side, at least the non-stop repetition of the words “Like a Boss” are made up with some twisted imagery, along with (host) Seth Rogen questioning the hell out of it. On yet another plus side, this wouldn’t be the last time something with a Pseudo-hip hop beat would be a part of the Lonely Island’s utility belt…



6. THREW IT ON THE GROUND (10/3/2009) – Or as I like to call this “Like A Boss version 2.0”; the beats stay and the flow remains tight, but gone (thankfully) is the repetition overkill; which is then replaced even sillier imagery, ample use of slo-mo, and a cameo from Frodo Baggins. This really is a more refined version of “Boss”; Samberg’s character remains brash & arrogant while at the same time receiving his comeuppance at the end, but at least this time around, the audience has a chance to breathe a little—this allows the audience to better appreciate the images of things hitting the ground.



5. BODY FUZION (2/3/2007) – Sometimes the “Good” Digital Shorts actually doesn’t have Samberg in it. This one featuring Drew Barrymore and most of the female cast is not only a good example of Samberg stepping away from the camera lens; but as a guy who loves cheesy nostalgia, the visual trappings of the piece almost makes the actual humor content an afterthought. The “Shot on Video” quality of the short gives it an extra layer of atmosphere that it didn’t really need, but was still a nice touch; especially during some parts where you see some genuine “Tape Chew”—you know, those lines of static that show whenever you eject the tape but it gets caught in the gears? (*SIGH* They really need to make VCRs again). Anyway, this “Shot on Video” style makes the activity all the more goofy to watch—especially if you’ve ever been exposed to an 80s workout video at any point in your lifetime—and it more than makes up for the lack of “Ha-ha” humor (Bonus points for the shout-out to WGBH Boston at the end).



4. JONAH HILL DATES ANDY’S DAD (3/15/2008) – One of the most important phrases I have ever learned in all my years of living is the oft-quoted Seinfeld line “Not that there’s anything Wrong with that” (also Demitri Martin’s “Not Gay, But Supportive”). So important were these phrases, that I was not only able to stomach the notion that Jonah Hill would have an affair with Samberg’s Father (played with sheer guts by SNL stalwart Jim Downey), but also the fact that a premise like this is actually one of the funnier entries the Island crew has to offer—especially when Hader gives us a punchline for the ages, which I’m not going to spoil here. But what I Really like about this is the fact that Jonah plays this up with 100% dead seriousness, even though the premise itself is patently absurd.



3. SERGIO [A.KA. “The Curse”] (1/30/2010) – Sometimes, nonsense makes all the sense in the world. Case in point, Jon Hamm popping up from out of nowhere to play a saxophone while shirtless because Samberg failed to heed the warning of a curse…yeah, it kinda makes more sense in practice than on paper—and not even then; yet, it still manages to work. Why? How? And more importantly, even though “that’s the joke”, is a shirtless guy playing sax really considered a “curse” when is should really be an annoying nuisance? The answer to all three of those questions is “Who the Hell Cares?!” Sometimes you need to throw in a good non-sequitur like “Sergio” in order to keep the audience on their toes; because too much “tried & true” is going to leave the audience feeling bored. So with that, hats off to Jon Hamm for playing something that leaves us scratching our heads, but still entertain us at the same time.



2. JACK SPARROW (5/7/2011) – Way back in the 90s, Hating Michael Bolton was a very easy thing to do—especially if you’re just a little kid, like I was back then. Just about everything about him made your skin crawl, even though by all outward appearances he seems like an OK guy. Hell, even David Spade took a swipe or two at him (“You’re Bald, and we All know it”). So when Bolton made an appearance here, my initial reaction sort of verged on “You’ve gotta be kidding me!” But then we get to the subject matter of Bolton professing his love for the “Pirates of the Caribbean” movies, and the reaction remains “Seriously, You’ve GOT to be kidding me!” For whatever reason, not only did this display the same kind of goofy surrealism the Digital Shorts often give us, but it actually accomplished the impossible—it helped make Michael Bolton “Cool”. So much so, that Bolton was actually able to Parlay that newfound cool into a cheesy, over the top Valentine’s Day special on Netflix. All of this leads to one more simple yet complicated question—if Andy Samberg can make Michael Bolton look cool, how come there isn’t a cure for Cancer yet? A short like this gives me hope that the impossible can be achieved.





LETTUCE & PEYOTE (2005) – Their first-ever short (and its sequel a few months later) needs to be mentioned; but also falls off the list because at the time this aired, there was certainly an aura of “WTF”. None of the viewers had any idea what the point of these bits were, nor did they have any idea that this would trigger a Domino effect of cultural relevance a little bit down the line…these two films were just weird…”Forte Weird” (which also explains why he’s in both of them).



NATALIE RAPS (2006) – Apparently the Lonely Island guys really enjoy their rap music. So much so, that they ask one of Hollywood’s more (shall we say) “Polished” actors to lay down a couple rhymes—thank god Portman has an Oscar now.



DEAR SISTER (2007) – As much as I appreciated this parody of Teen Dramas (Particularly “The OC”), this falls off the list because of poor timing. Several days after this aired, a mass shooting at Virginia Tech took place. I’m sure that was a coincidence, but considering the fact that this piece also involved multiple gunshots, forgive me for thinking that was slightly uncomfortable to watch after the fact.



DAIQURI GIRL (2008) – To this day, I’m still not sure if the poor production skills or the crawl explaining the poor production skills were actually intentional or not; but even with the most minimal of effort, if there’s still at least one laugh to be had, it’s doing its job.



JAPANESE OFFICE (2008) – The parody itself was standard issue, but it manages to scrape into the “Honorable” section (no pun intended) thanks to the mere presence of one Mr. Gervais—who, quite honestly, should’ve hosted at least 6 times by now…if Ever



LAZY SUNDAY II (2012) – “On these New York streets I honed my fake rap penmanship, That’s how it began, and that’s how I’m a Finish it (*GUNSHOT, SMASH CUT TO BLACK*)”…except, of course, for the handful of shorts Samberg did whenever he came back to host/cameo, but let’s not worry about those.



With over 100 of these shorts to go through, Missing a couple of them seems inevitable. So please, feel free to comment on some of your favorites if I missed any; and hopefully this summer, there will be a “Viewer’s Choice” of More shorts.



TOMORROW: As what could potentially be the last show of the year wraps up (Long Story), we look at the last time Jimmy Fallon giggled his way through the holidays.



3 thoughts on “The (CHRONIC, WHAT?!) Top 8-ish SNL Digital Shorts

  1. Casey Killingsworth says:

    The air dates on the first two entries on your list are mixed up. Harpoon Man actually aired 10/21/2006 (post “Lazy” but pretty “Dick”) and Like A Boss actually aired in 2009 NOT 2007.


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