What does Chappelle’s “leverage” reveal about power, comedy, and our increasingly disoriented public life?

Scott Douglas Jacobsen asks for quick thoughts, and Rick Rosner riffs on a new Dave Chappelle Netflix special as a lesson in leverage—insight plus access. He praises Chappelle’s connective storytelling, contrasts it with MAGA access without understanding, and cites a devastating AIDS-cure setup that ends in blunt deflation. Rosner says Chappelle has earned slower, perspective-first comedy, then widens to modern disorientation: post-iPhone “lost generations,” endemic COVID cognitive effects, and propaganda. He closes with Archimedes as metaphor and notes late-night’s collaborative leverage, pointing to Jon Stewart and Jimmy Kimmel as sharp insiders with teams, who turn daily chaos into workable sense.

Scott Douglas Jacobsen: Any quick thoughts? 

Rick Rosner: I just watched the new Dave Chappelle special on Netflix. I kept thinking about leverage—the mix of insight and access. Chappelle is exceptionally smart and perceptive, and his life has given him exposure to an enormous range of people and experiences.

You saw how he wove John McCain, Martin Luther King Jr., Nipsey Hussle, Stevie Wonder, and even that 1990s holistic AIDS doctor into a single narrative. He connects them in a way that generates understanding rather than just references. I found it admirable and instructive, and it made me sad that the country is politically dominated by people with little insight.

At the end, they show a montage of Chappelle with a huge range of cultural figures—from Sean Combs and Paul McCartney to Bill Murray, Madonna, and Quincy Jones. I could probably identify two-thirds or maybe three-quarters of them, but the precise number is not the point. The point is that Chappelle has access and perspective. MAGA politicians and Trump have access, but not insight.

That is what frustrates me: power in the hands of people who neither understand the world nor want to. Chappelle has listened to everyone and drawn meaning from it. Trump’s skill set is persuading people to give him money, manipulating them, and avoiding consequences. Chappelle is the opposite—he once walked away from extraordinary power and success because it conflicted with who he was. Someone driven purely by wealth and celebrity would not have done that. He later returned to the spotlight, but only after years abroad shaping his own worldview.

Trump’s instinct is transactional: finding another angle, getting another hundred million, pushing boundaries until someone stops him. It is exhausting to know that Trump is president and Chappelle is not.

Jacobsen: What was your favorite joke from the special?

Rosner: The one that hit hardest for me was the story about Charlie Barnett, one of Chappelle’s mentors, who was dying of AIDS. Chappelle recounts taking him to a doctor named Sebi—an alternative practitioner who claimed to cure AIDS holistically and who fought off government lawsuits over those claims. Chappelle says, “You’re not dying on my watch,” and brings Barnett to Sebi. Then he adds: “And three months later, Charlie Barnett was dead of AIDS.” The timing, the delivery, and the brutal abruptness made it the most powerful moment for me.

It earned a huge laugh because Chappelle sets up this narrative about a supposedly miraculous AIDS cure, connects it to the conspiracy theories around Nipsey Hussle’s murder—since Hussle was making a documentary about that doctor—and then punctures the fantasy by admitting the doctor could not save his own friend. That deflation is the essence of the joke, and the special builds toward it for nearly twenty minutes. It is the most memorable part for me as well, even if I thought the special overall was weaker than his strongest work.

If what you want is nonstop laughs, this special is not that. Chappelle basically tells the audience: brace yourselves, this is going to take twenty minutes, stay with me. He even pauses to ask whether people are bored. It reminded me of how Lenny Bruce stopped chasing laughs near the end of his career—not because he transcended comedy, but because he was falling apart under pressure, harassment, and addiction. Chappelle is not falling apart. He is choosing to stretch form, braid stories, and deliver fewer jokes in exchange for perspective. I think he has earned the right to do that because the narrative itself is compelling and reflects the world he inhabits, which is increasingly the world the rest of us inhabit too.

Near the end, he tells the audience that all we can do is outlast “the orange motherfucker,” and the delivery works because it comes after this long, labyrinthine buildup. The whole thing feels difficult to perform—thousands of words held together without losing the audience—and I imagine he repeated that structure dozens of times before taping.

What I also enjoyed is how Chappelle weaves in the Puffy Combs material. He talks about Combs being prosecuted and how Chappelle keeps getting invited to places where he fears he is about to stumble into one of Combs’s infamous “freak-offs”—events where young women were allegedly subjected to coercive sexual situations. Chappelle plays the tension between curiosity and revulsion: maybe he once would have gone along, but now he loves his wife, wants nothing to do with that world, and would get out immediately. The joke is that every time he thinks he is about to witness a freak-off, he instead encounters something that expands his understanding of how people and power work.

That pattern—being close enough to the worst of the world to see it clearly, yet still extracting meaning from it—reminds me of Darwin. Darwin had insight, but he also had access: five years circling the globe on a ship because the captain needed company to keep his mind stable. Opportunity plus insight equals leverage, and Chappelle has both. He keeps finding himself near the machinery of power and vice, and instead of drowning in it, he returns with sharpened perspective.

I liked the special. Maybe part of it is that it flatters me to like it. I am a sucker for work that makes me feel like I am seeing connections, understanding something larger. After that, I started watching Eden, the Ron Howard film with Jude Law, Sydney Sweeney, Ana de Armas—big ensemble cast. It is about people who fled Germany in the late 1920s and early 1930s to escape what they saw coming and to build a community elsewhere.

With Eden, early in the film someone says, “The world has gone mad. It is 1929.” And historically, the world really did feel that way. A decade earlier, the Spanish flu infected hundreds of millions of people worldwide and left many with lingering neurological and psychological effects. You had a postwar boom, then a global economic collapse, the rise of fascism in Italy in 1922 and then across many countries, and eventually a second world war ending with atomic weapons.

Whether or not the flu literally altered people’s minds on a massive scale, the social and political conditions were enough to make populations behave irrationally. And that sense of disorientation is even stronger now.

People refer to the cohort after World War I as the “Lost Generation”—the artists and writers disillusioned by the war, often gathering in places like Paris. I think every generation since the iPhone is becoming its own lost generation, because the digital world disorients us constantly.

The world was already too complex for individuals to grasp a century ago, and it is vastly more complex now. Most Americans feel insecure and displaced, and that feeling is not confined to America. The pace of disruption is relentless. People who claim to feel perfectly centered are often performing certainty they do not possess.

Humanity as a whole is living in permanent disorientation and disruption. And barring some radical change in how our systems and technologies interact with us—and how we interact with them—I do not see that easing.

It is going to be the norm. COVID has not helped; it is now endemic and affects cognition, and propaganda does the same. I do not know if there was ever a point in history when our brains were better suited to handle this level of complexity, but here we are. As my late mother-in-law used to say while struggling with dementia, “a lot of things are going on.” She said it to excuse memory lapses, but she was not wrong.

One more thought connecting back to Chappelle and leverage. Archimedes said that with a place to stand and a fulcrum he could move the earth. He was talking about the physics of levers, though the line works metaphorically too. I described leverage as insight plus access. Chappelle has leverage: his mind is the lever, and his exposure to the world is the fulcrum. He may not be able to move the world, but he can analyze and interpret it more effectively than most people.

And he is not the only one. In that photo montage at the end of the special, you see him with Jon Stewart and Jimmy Kimmel. Those guys also have leverage: they are sharp, they meet everyone, and their jobs require them to understand what is happening. They have to produce material every day, so they are motivated to stay culturally literate, and they hire teams of smart people to help them. Late-night comedy is too large and fast-moving to do alone.

I doubt Chappelle uses writers in the same way most stand-ups do. But late-night hosts rely on collaborative leverage: ten or twenty writers generating angles and jokes constantly. Kimmel reportedly contributes a significant portion of his own material, which is unusual for someone producing at that scale and quality. Others, like Craig Kilborn according to industry stories, would simply show up and read jokes written for them.

Award-show hosts and late-night anchors routinely work with teams who generate a thousand joke ideas and winnow them down to the best few dozen. That collective effort deepens understanding because you are surrounded by perceptive people whose job is to help you refine your engagement with the world. Kimmel has a staff of more than two hundred people, many of them highly capable, and their entire project is to dissect the world four nights a week. That is an enormous source of leverage in making sense of things.

Rick Rosner is an accomplished television writer with credits on shows like Jimmy Kimmel Live!, Crank Yankers, and The Man Show. Over his career, he has earned multiple Writers Guild Award nominations—winning one—and an Emmy nomination. Rosner holds a broad academic background, graduating with the equivalent of eight majors. Based in Los Angeles, he continues to write and develop ideas while spending time with his wife, daughter, and two dogs.

Scott Douglas Jacobsen is the publisher of In-Sight Publishing (ISBN: 978-1-0692343) and Editor-in-Chief of In-Sight: Interviews (ISSN: 2369-6885). He writes for The Good Men Project, International Policy Digest (ISSN: 2332–9416), The Humanist (Print: ISSN 0018-7399; Online: ISSN 2163-3576), Basic Income Earth Network (UK Registered Charity 1177066), A Further Inquiry, and other media. He is a member in good standing of numerous media organizations.

Photo by Bogomil Mihaylov on Unsplash

Last updated May 3, 2025. These terms govern all In Sight Publishing content—past, present, and future—and supersede any prior notices. In Sight Publishing by Scott Douglas Jacobsen is licensed under a Creative Commons BY‑NC‑ND 4.0; © In Sight Publishing by Scott Douglas Jacobsen 2012–Present. All trademarks, performances, databases & branding are owned by their rights holders; no use without permission. Unauthorized copying, modification, framing or public communication is prohibited. External links are not endorsed. Cookies & tracking require consent, and data processing complies with PIPEDA & GDPR; no data from children < 13 (COPPA). Content meets WCAG 2.1 AA under the Accessible Canada Act & is preserved in open archival formats with backups. Excerpts & links require full credit & hyperlink; limited quoting under fair-dealing & fair-use. All content is informational; no liability for errors or omissions: Feedback welcome, and verified errors corrected promptly. For permissions or DMCA notices, email: scott.jacobsen2025@gmail.com. Site use is governed by BC laws; content is “as‑is,” liability limited, users indemnify us; moral, performers’ & database sui generis rights reserved.