The Wicked Witch of the Web 😈

The genesis of my sketch comedy journey; a build-in-public road to SNL.

A special piece that features my foray into sketch writing as a storytelling outlet. Shoutout to my troupe at Magnet Theatre — Broken Premises — for their feisty, funky, & fun feedback!

Lately, I've been tapping more into the creative part of my identity, even venturing outside the comfortable ambiguity of the improv stage. Instead, I wanted to expand my toolkit with sketch comedy, which places a heavier emphasis on storyboarding and smart humour injected intentionally. In many ways, sketch is even more of a hairy beast than improv. You’re making a bet on one core concept and fleshing out a story arc entirely. You can’t iterate on the live environment with your quick-witted scene partners, and it’s hard to tease out games and plotlines with no immediate reactions. Every stroke of genius that gives birth to a Borat-level character comes with hundreds of half-baked duds and dead script skeletons. My instructor’s response to most of my sketches: “Decent setup and wordplay, go further with each beat, not enough jokes.”

What inspires me the most to explore comedy as an art form is how it combines multiple sources of media together — dramatic screenplays, stage performance, video production, and written speech — to convey unique points of view. It helps me realize that language is truly the most decentralized technology we have. A timeless tool for transformative thought that is both universal, yet nuanced for any individual. By cleverly applying aspects of language and speech, you're free to explore complex concepts and thoughtful themes about anything, in a lighthearted playful manner.

I think this kind of narrative structure is so freeing and raw. Taking from both the world and from within. Knowing that the simplest way to “get laughs” is to just stay absolutely authentic and true to your own way of worldbuilding. That’s the ultimate goal for me: to draw from every single aspect of my reality to become a multimedia comedian. If I manage to keep up this enthusiasm, this might be the start of a super ambitious goal: to aim for the SNL staff writer role one day. A true creative aspiration!

The following sketch is a 3-hour brainchild, where I challenged myself to craft a parody in the style of SNL's Weekend Update. The format takes the traditional news broadcast and organizes skits & jokes based on topical current events. Here's the result of combining my fascination with the technology world with a nod to the iconic Wizard of Oz. Presenting my inorganically organic work, “Wicked Witch of the Web”:

I'll be peppering in brief commentary throughout this script about my creative choices and moments of inspiration drawn from personal experiences. The premise of using the web as a window into the world gave me lots of flexibility and variables to play with, especially with my goal of creating a more mischievous tone. The first beat builds the backdrop and develops the universe: Who is this witch? What does she really care about? How does she view the world and the web?

Wicked Witch Weekend Update Sam Wong Vf
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At the outset, I needed to make this witch character just as malevolent as her counterpart in Wizard of Oz. This meant pulling from the witch's motivations, quirks, patterns, and symbols — all in the context of this new digitally-informed landscape. That’s the main catch with writing monologues instead of the multi-character skit format. Breadth is replaced with depth. The main subject has to feel fully fleshed out. The line “Double, double, toil and trouble. Emails burn & notifications bubble” is actually taken from the witches in Macbeth, but I weighed giving her an almost poetic voice as more important than strictly staying in the narrative bounds of Oz. The audience learns about her devious goals and holier-than-thou attitude, as she harshly dismisses vanilla white hat hackers as just “sweaty programming peasants”. Sorry, developers!

To replicate the SNL personality, I dedicated the second beat to incorporate more physical comedy into the scene. The classic stirring-of-the-cauldron motion harks back to a witch's core means of creation: magic potions. Blending the visceral imagery with cooking metaphors expands the scope of horror and hilarity. This choice also accentuates the witch's crazed craving for causing turmoil on the web. At this phase of the script, I embrace the creative direction by exposing hints of the bigger picture and taking jabs at current events. For example, the monolithic entity of “Big Tech” often gets a lot of flak for designing addictive user experiences to convert attention into monetization (e.g. TikTok’s secret). This results in an extractive race to the bottom mindset. The witch is fully aware of this. “Digital destruction” is her goal, after all. In a sobering twist of fate, the institutional power now resides in the hands of a slick sorcerer who casually controls the levers of online virality and toxicity.

This third beat is where the sketch escalates further by layering in a subtle societal sub-commentary on sensitive tech topics: cybersecurity and continuous consumption. While we're desensitized to algorithm-centric products like TikTok and Twitter — masking as essential tools through their ubiquity and utility — we’re actually more conscious of things that explicitly affect our quality of life. Everything from technical bugs that limit our communication to the charm of magic money that is mysteriously programmable, capitalizing on our interest and ignorance. Importantly, this sketch centers around the idea of pinning a single source of blame (the Wicked Witch of the Web) to all the problems of being too plugged in. Imagine a world where we could re-direct all our frustrations to a single named body and re-allocate our priorities to dismantle these broken systems in place. Note: I also go crazy with the tech puns, associating ghoulish & Google and giving Slack and Zoom some quick cameos too!

You also can’t escape the presence of crypto while surfing the web nowadays. The promise of an ownerless, borderless, decentralized internet is in the name of pure prosocial value, but this sentiment is often corrupted by the focus on financialization. In other words, the mass market shilling of so-called “shitcoins” promises riches beyond anyone’s imagination. Again, we see the strength of skating across real truths of our current reality through comedy. It’s not a surprise that I make the witch take full advantage of such manic energy, which sets up for the ultimate curtain call:

A Meta Commentary 🧬

Unlike most SNL Weekend Updates that present their climax as a buildup of previous jokes, my ending conjures a different twist. Just when you think the witch is done with her technological tirade, she shows her final hand and transforms the host into an internet troll. When I first thought of this idea, I almost laughed my way out of this framing. Way too silly, not enough substance, right? Then I remembered what all my improv & sketch teachers had drilled into my mind: be absurd only if you can be specific and believable. Since the callback is derived from the witch's supposed spell-based superpowers, the troll joke doesn't betray her character’s philosophy. Rather, it adds a splash of depth into the mix! It also gives me the liberty to call out the not-so-pleasant parts of internet sub-forum culture on open hivemind platforms like Reddit.

There were also many other technical concepts I could have sprinkled into the story: antique web relics (paywalls, targeted ads, malware), explicit callouts with witchcraft wordplay (Apple & poison apples, Facebook & spellbooks), and deeper extensions of the witch's universe (dark web, blockchains). In my view though, the cherry of this script is giving space for the witch to inhabit her own mysterious cryptic vibe through lyrical dialogue. The best thing about crafting a monologue with a well-known muse is that the tried-and-true tropes already exist as scaffolding. So instead of stressing about custom character backstories, the decisions become simpler: how do we apply these pre-vetted LEGO pieces to the funny social commentary we want to propel?

At the end of the day, writing sketch comedy requires difficult trade-offs, and there's no way of telling how audiences will react to jokes until the moment they're executed. If I’m honest with myself, I don’t think my work is conventionally funny — my brain doesn’t default to cheeky one-liners like sensational standup artists. There is a silver lining though. As long as I stay true to the characters and the environment, there are “no wrong choices”; only different pathways that hopefully coalesce into a sound story. Only then will the laughs naturally come!

There’s one quote that has always stuck with me since the improv training days:

“The times we're living in just defy all logic. So we find and make truth in comedy by doubling down on absurdity and commenting on human nature authentically

And to me, personal authenticity is the most beautiful part of the comedic creative process :)

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