Based on the satirical techniques and style observed in Bess Kalb's work at The Grudge Report and her broader satirical journalism career
Writing Technique: Personal Stakes + Political Commentary
Today I wrote about RFK Jr.'s war on psychiatric medication, and I realized something crucial about satirical writing: the most powerful satire comes from your own blood.
When I sat down to write "Hooray for Pills," I could have approached it like a traditional op-ed—statistics, expert quotes, logical arguments. Instead, I started with the most vulnerable truth I could tell: "Since I was 19 years old, I have been on depression medication."
The Teaching Moment:
Lead with your skin in the game. Don't write about abstract policy—write about how that policy would destroy your actual life.
Use medical precision for emotional impact. Notice how I described ulcerative colitis making "13 hours of unmedicated active labor unnoticeable." Specific, clinical, devastating.
Let rage fuel research. My fury at RFK Jr. made me dig deeper into my own story, which made the satire sharper.
The formula: Personal vulnerability + righteous anger + surgical precision = satirical gold.
Link: Jimmy Kimmel Live! writing techniques
Writing Technique: Document Parody + Class Commentary
This piece taught me that format can be funnier than content. I wrote a fake Harvard rejection letter to Barron Trump, and the comedy came from the bureaucratic language colliding with obvious truths.
The Craft Breakdown:
Master the language of institutions. I studied real Harvard rejection letters until I could write in their voice perfectly.
Let the format do the work. The comedy isn't in making jokes—it's in using formal language to say what everyone's thinking.
Find the uncomfortable truth everyone knows but won't say. Nepotism in elite admissions isn't funny. A rejection letter that accidentally admits it is hilarious.
Key Line: "While your father's financial contributions to various institutions are noteworthy..."—this isn't a punchline, it's a documentary statement dressed as bureaucracy.
The lesson: Sometimes the best satire is just institutional honesty.
Link: Harvard College admissions
Writing Technique: Strategic Vulgarity + Cultural Specificity
"You think you can cut funding to NPR? To Fucking National Public Fucking Radio?"
Today I learned that strategic profanity can be satirical precision. Not random swearing—targeted outrage that mirrors how real people actually talk when they're genuinely furious.
The Technical Elements:
Know your audience's sacred objects. NPR listeners have specific devotions: Ira Glass, Terry Gross, that particular brand of liberal intellectualism.
Catalog the specific details. "Celestial Seasonings Decaf Lemon Zinger Tea with a Claritin chaser"—this isn't made up, this is anthropological research.
Let class anxiety fuel the comedy. The fear isn't just losing NPR—it's losing the cultural markers that separate "us" from "them."
The Realization: The best satirical rants aren't about the big issue (budget cuts) but the tiny, specific losses that reveal who we really are (Terry Gross's tea budget).
Link: NPR funding facts
Writing Technique: Contrarian Positioning + Deadpan Absurdity
"I am honored to be writing the only article saying resoundingly that I think it was good. And cool."
This piece taught me about satirical false flags—pretending to defend the indefensible to expose how stupid the whole conversation is.
The Architecture:
Take the opposite position from everyone else. When the internet was mocking Bezos's space penis, I wrote a defense.
Use corporate language to describe human absurdity. "Normal-looking space ship thrust its tip through the earth's atmosphere"—I'm describing a dildo flight in press release language.
Double down on the least defensible aspects. The more ridiculous my defense, the more obvious the real criticism becomes.
The Meta-Game: I'm not really defending Bezos. I'm making fun of how we talk about rich people doing stupid things. The satire is in the defense itself.
Link: Blue Origin mission details
Writing Technique: Micro-Aggression Macro-Analysis
"The man in my parents' old building who pressed the 'DOOR CLOSE' button as my kid was entering the elevator."
Today I discovered that the smallest betrayals make the best satire. Not war crimes—elevator crimes.
Why This Works:
Everyone has this exact experience. The door-close button guy is universal, which makes the rage instantly relatable.
Escalate the language, not the crime. I write about this minor rudeness with the intensity of a war crimes tribunal.
Let your own petty rage become the subject. The joke isn't just the guy—it's how disproportionately angry I am about it.
The Deeper Truth: We live in a world where we have to pretend micro-aggressions don't matter, but they're actually how we measure the collapse of human decency.
The formula: Tiny betrayal + enormous reaction + precise description = perfect satirical proportion.
Link: Urban etiquette studies
Writing Technique: Satirical Journalism Structure + Character Voice
Today I wrote a fake interview with "White Afrikaner Refugees" in America, and I learned that character creation is satirical architecture.
The Technical Framework:
Build a complete character voice. "As a racist, there was no place we felt more comfortable than America." This character has full internal logic.
Use journalistic format for satirical content. Q&A structure makes the absurdity feel documented.
Let the character reveal the truth accidentally. The best satirical characters don't know they're exposing themselves.
The Dangerous Territory: This piece walked the line of satirical risk—using racist perspectives to expose racism. The key is making sure the character damns themselves, not that you're echoing their views.
The Lesson: Great satirical characters are too oblivious to realize they're confessing.
Link: Immigration policy analysis
Writing Technique: Format Hijacking + Political Metaphor
"Dust off your performative boots and get in line for the Hillbilly Two Step with America's favorite Appalachian Yale Graduate!"
This piece taught me about format as satirical weapon. Taking game show language and applying it to political horror.
The Breakdown:
Study the original format obsessively. I watched actual game show promos until I could write in their manic, exclamation-point voice.
Map political reality onto entertainment structure. JD Vance becomes a dancing partner; abortion rights become a game show wheel.
Let the format's cheerfulness clash with the content's darkness. The cognitive dissonance IS the joke.
Key Insight: The most effective political satire doesn't argue with power—it reduces power to entertainment, which is actually more insulting.
Link: Game show format analysis
Writing Technique: Trauma as Truth-Telling + Satirical Sincerity
Sometimes satirical writing means putting down the satirical tools and just telling the truth with surgical precision.
"One November morning I was seated at my desk... writing my morning joke assignment for the late night TV show... when I felt the smallest, barely perceptible sense that something was suddenly falling."
What This Taught Me:
Satirical writers need to earn their darkness. You can't just be mean—you have to show you understand real pain first.
Sometimes the most radical thing is to stop being funny. In a world of constant irony, sincere vulnerability becomes subversive.
Use your platform for more than just jokes. The same audience that laughs at your political satire needs to hear about real human experience.
The Technical Choice: Notice the shift from satirical voice to straightforward narrative. The power comes from dropping the performance when the stakes get real.
Link: Pregnancy loss support resources
Writing Technique: Industry Insider + Cultural Criticism
"To kill a late night show is also to kill an enormous platform for speaking truth to power."
This piece taught me that your day job can be your satirical subject. I wrote about late night TV from inside late night TV, using my access as analytical leverage.
The Insider's Advantage:
Use your professional knowledge as satirical ammunition. I know how many people watch Colbert because I work in this world.
Critique the industry while defending its importance. The tension between loving something and seeing its flaws clearly.
Let your career anxiety become cultural criticism. My fear of losing late night TV jobs becomes analysis of losing democratic discourse.
The Meta-Level: Writing about satirical TV while doing satirical writing—the form mirrors the content.
Link: Late night television analysis
Writing Technique: Identity Politics + Nuanced Positioning
"I think there's twice as many opinions about Judaism as there are Jews in the world."
Today I learned that the most difficult satirical writing involves your own identity under attack.
The Impossible Balance:
Write from your specific position without claiming to represent everyone. "I'm writing as who I am, which is a Jewish mom in the United States."
Acknowledge complexity without abandoning moral clarity. You can hold multiple truths without falling into false equivalencies.
Use humor to handle what's too painful to address directly. Sometimes a joke is the only way to say something true.
The Hardest Lesson: Sometimes the most satirical thing you can do is refuse to satirize. Some moments require sincerity, not cleverness.
The Final Rule: Satirical writing isn't about being funny. It's about being brave enough to tell the truth in a way that makes people listen.
Link: Jewish identity and comedy
After studying these 10 pieces, here are the core techniques:
Personal Stakes First: Start with your own skin in the game
Format as Weapon: Use institutional language against itself
Strategic Vulnerability: Share real pain to earn satirical authority
Micro-Focus: Small betrayals reveal macro truths
Character Creation: Let people damn themselves through their own voices
Industry Insider Knowledge: Use your day job as satirical material
Contrarian Positioning: Defend the indefensible to expose the actual problem
Precision Over Punchlines: Surgical accuracy beats clever wordplay
Know When to Stop Being Funny: Sincerity can be more subversive than irony
Cultural Anthropology: Study your audience's sacred objects and fears
The Ultimate Truth: Great satirical writing isn't about being mean to bad people. It's about being honest about what we're all pretending not to see.
August 2024 - Writing Technique: Absurdist Practical Advice + Escalating Desperation
Today I wrote my holiday conversation survival guide, and I discovered that the most effective satirical writing comes from genuine terror masked as helpfulness.
The piece started as a real problem: How do you maintain family relationships when half the table thinks the other half are literal Nazis? But instead of writing another hand-wringing think piece, I decided to treat it like a genuine emergency preparedness manual.
The Technical Breakthrough:
Start with false optimism. "Congratulations! If you are reading this, you have physically survived a holiday this year!" - immediately establishes that survival itself is an achievement.
Escalate the suggestions from reasonable to unhinged. We go from "talk about the weather" to "jam meat gristle down your throat to fake a choking emergency."
Use instructional format for maximum absurdity. Nothing's funnier than step-by-step directions for emotional terrorism.
Key Line Analysis: "Should someone start loudly lecturing someone else about fragments of ancient Jewish pottery shards in southern Canaan, just turn your wrist slightly and say, 'In five minutes, it will be six o'clock!'"
This works because it's both completely useless and oddly specific. The phrase "fragments of ancient Jewish pottery shards" is precisely how family fights about Israel-Palestine actually sound—archaeological and completely insane.
The Shadow Spider Technique: "Sorry - Is that a shadow or a spider on your forehead?" This isn't just a distraction—it's psychological warfare disguised as concern. I'm teaching readers to gaslight their relatives for the greater good of family harmony.
The Escalation Pattern:
Weather (harmless)
Time (slightly more desperate)
Fake medical emergency (full psychological breakdown)
Accept meat consumption despite vegetarianism (moral compromise for survival)
What I Learned: Sometimes the best political writing isn't about politics at all—it's about the domestic consequences of political division. The real subject isn't holiday dinners; it's how democracy dies one family argument at a time.
The Meta-Joke: I ended with Wendell Berry's "The Peace of Wild Things"—a genuine, beautiful poem about finding solace in nature. After 800 words of satirical family warfare tactics, I offered readers actual peace. The contrast makes both the satire sharper and the poetry more necessary.
The Teaching Moment: Great satirical advice pieces should feel both completely useless and desperately necessary. If your family really needs this guide, it's already too late. If they don't, it's hilarious.
August 2024 - Writing Technique: Format Parody + Micro-Grievances as Macro-Politics
I just wrote my Presidential Address about a playground incident, and I learned that the most devastating political satire comes from treating tiny personal slights with the gravity of international incidents.
"My Fellow Americans, For the past four years, it has been my honor to serve you as your president. Most of you. Really all of you except Kai, who just pushed Bess Kalb's son down on the playground in the park out of fucking nowhere."
The Architecture of Absurdity:
Use the exact language of institutional power. I studied actual presidential addresses until I could perfectly mimic that cadence and tone.
Insert completely personal grievances into matters of state. The cognitive dissonance between "My Fellow Americans" and "this specific child named Kai" is where the comedy lives.
Escalate the personal into the political. One playground push becomes a matter of national security.
The Technical Genius: By the end, I'm using presidential emergency powers to address playground behavior. "Furthermore, effective immediately, all swing sets will be under federal oversight, and timeout will be administered by the Department of Justice."
Why This Works:
Everyone has been in this exact situation. Every parent has wanted to call the National Guard over playground injustice.
The format gives permission for rage. Putting your petty fury into presidential language makes it both ridiculous and cathartic.
It exposes how actual political rhetoric works. Real politicians do weaponize official language for personal grievances—I'm just being honest about it.
The Deeper Commentary: This isn't really about playground behavior. It's about how we process powerlessness in daily life. When you can't control global politics or national injustice, sometimes you just want the President to address the fact that Kai is a little asshole.
The Form as Content: The joke isn't just what I'm saying—it's that I'm saying it in presidential address format. The medium IS the satirical message.
The Craft Lesson: The best satirical format parodies don't just use the format for comedy—they expose what that format is actually used for in real life. Presidential addresses ARE often about personal grievances dressed up as national concerns.
For more satirical journalism techniques, visit The Grudge Report and Bohiney Magazine