Demetri Martin and Windows Vista

Since we are still on Demetri Martin March here at SUCH, I thought it would be fun to do a deep dive on what I imagine to be a now-forgotten piece of his comedy career: the viral web campaign for Windows Vista.

You know Windows Vista, right? If not, here’s a clip from the British sitcom The IT Crowd that demonstrates how hated it was by the ubernerd Moss (played brilliantly by Richard Ayoade).

Moss: What kind of operating system does it use?

Bomb-disabling guy: Uh…Vista!

Moss: We’re going to DIE!

Yes, the much-maligned operating system—known for being very slow and incompatible per this article from ZDNet and the obvious butt of the joke in that sitcom clip—was at one time tied to Demetri almost exclusively. He was THE face of the product for Millennials, and luckily for him, it seems no one except me even remembers CLEARIFICATION.

Microsoft's decision to hook up with Martin bodes well for the company's bid for coolness, says Samantha Skey, senior vice president for strategic marketing of New York's Alloy Media + Marketing, providers of nontraditional targeted media and promotional marketing programs aimed at the under-30 "millennial" crowd. "Choosing Demetri Martin is smart in that you're going for a character that just inherently is going to identify you as fairly cool with young adults, because he doesn't have mass appeal yet," Skey maintains, adding, "This mouthpiece was chosen really carefully, clearly, with the millennial audience in mind."

So let’s take a closer look at Demetri’s viral marketing campaign with Microsoft.

The Webisodes

It’s difficult to recall (we’re talking nearly two decades ago), but there was a time when the Internet had no video repository that everyone used. Prior to YouTube, videos called webisodes—an obvious portmanteau of “web” and “episodes”—were hosted exclusively on company websites.

Here’s Demetri explaining how they work (and how ebisodes are about tides haha).

I remember tuning in to view shows like Clark and Michael (a hilarious show featuring a very young Michael Cera and Clark Duke making their way as writers in Hollywood) and Burning Love (a sendup of The Bachelor that I had been obsessed with WAY before my husband Jeff showed me an episode of the ABC dating reality show) on their respective websites in the early aughts.

The best season of Burning Love is the second one because it had SO many of my favorite male comedians/actors: Adam Brody, Nick Thune, Ryan Hansen, Michael Cera (notice a pattern?), Kumail Nanjiani, Rob Huebel, and Joe Lo Truglio in this screenshot alone.

Like those programs, Demetri’s webisodes were only available on a website: clearification.com. Don’t bother clicking on that link by the way—the URL is long gone and redirects to a site about some author named Andy Chaleff.

But back in 2006, the website was up and running as a vehicle for subtly promoting Microsoft’s newest OS. I found a short YouTube video about CLEARIFICATION that includes clips of what the website looked like (very nostalgic for me…I had completely forgotten that it had info about his comedy tour for example).

Anyway, that second screenshot gives you an idea of how people in 2006 could view the webisodes.

At the time, there were six episodes that depict Demetri learning how to achieve clarity in his life through the Institute of Advanced Personhood (and obviously Microsoft Vista). Funnily enough, the first two of the series say there were originally seven webisodes planned, but I suppose the order was cut down at some point and no one ever updated the title screens.

Today, there are only four webisodes available to view on the official YouTube channel (episodes 4 and 6 appear to be lost in the sands of time).

Episode 1: The series begins with a look into Demetri’s chaotic life where he emulates a crazy businessman who drinks full coffee pots of coffee, screams at everyone, and is super competitive. His character suffers from HAND TOSS (Hyper-Achiever with No Direction and Tendency to Overcomplicate Situations Syndrome).

Demetri’s Important Presentation: Leverage Levers and Liquidate Liquids. Note the characteristic lightning bolt and stars from These Are Jokes!

Episode 2: The second installment on the website provides our first look at the Institute for Advanced Personhood, a whimsical place straight out of a Wes Anderson film and/or Severance (particularly in terms of the origin story of the institute). My favorite part is Demetri’s “water bottle.”

Episode 3: The third installment (and first one to let us know there are now 6, not 7, parts) is the trippiest of the bunch. Demetri has his brain explored by the doctors, which results in a “Yellow Submarine”-esque animated scene. Very fun!

Episode 5: The final webisode still available is about nature and includes Demetri running around a forest in a squirrel suit. I also really want to try out that human-sized hamster wheel!

Thoughts

While the mini movies are pretty cool, what I remember best about the website are the Thoughts animations. You can find lots of these online today (not all of them though, sadly), and each one is a little gem of an animated Demetri with a blue-and-white baseball tee, brown pants, sneakers, and a messenger bag saying whatever he wanted about any topic. These short clips are like a stream-of-consciousness look into Demetri’s mind (which I guess relates to the whole CLARITY thing they were going for).

Each clip takes place in a whimsical location with him sitting on a log, on a dodo (very Alice in Wonderland), on a bird’s nest, and a few other places. If you’re a fan of his comedy or just enjoy dry observational humor, I highly recommend you check out these bits on YouTube.

Here are some of my favorites:

1. Demetri Martin Cereal: Demetri explains his thoughts on cereal and its often-magical mascots. This is one I really enjoy as a cereal connoisseur.

2. Demetri Martin Windows Vista: Demetri struggles with pronouncing the name “Vista.” This one is cute and explains that it’s not Vee-sta. Demetri also rambles in a variety of accents before saying he’s auditioning for the role of an idiot.

3. Demetri Martin Touring: This is why I adore his comedy. Clever wordplay with “pee in” vs. “pee on” taken to a very silly extreme? Yes, please!

4. Demetri Martin Sober: Another very funny clip, this time about there not being any good synonyms for “sober” compared to “drunk.”

5. Demetri Martin Clickoff: Demetri comes up with a new insult for the digital age. Click me? Click YOU!

So that was Microsoft Vista’s attempt to capture the Millennial market through the intellectual humor of Demetri Martin. While the OS has ultimately gone down as one of the worst ever, I’m glad we still have these entertaining videos and animations to watch twenty years later.

I hope you’ve enjoyed this exploration of a forgotten part of comedy history. Stay tuned for more Demetri Martin fun this month!