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  • Writer's pictureKen Shaw

Warrior Wisdom: Red Spandex Instead of Toga’s — Deadpool as a Model of Ancient Skeptic Philosophy

Need a laugh? Contemplate Deadpool walking among the Ancient Greeks schooling them in thought. That’s what we’re doing here — and there’s a surprising amount we can learn from Deadpool to help us in our lives.

Audience: leaders looking to add some humor and philosophy to their lives. And any fans of Deadpool and MAXIMUM EFFORT!!!!

He loves you, he loves me, and he sure as sh*t loves himself! But most importantly — he loves life and by channeling his inner Skeptic can laugh in the face of any challenge. Wouldn’t that be great?

1. The Skeptic in Spandex: How Deadpool Epitomizes Ancient Skeptic Philosophy

Mouthy Merc: If you thought Deadpool, the Merc with a Mouth, the epitome of red-suited irreverence, and, in his own words, a “foul-mouthed mutant mercenary,” could have anything to do with philosophy, well, pat yourself on the back! Because apparently, our beloved, fourth-wall-breaking antihero is a covert philosopher, embodying the timeless wisdom of ancient skeptic philosophy. Now, before you choke on your chimichanga, let’s dive into this unorthodox yet tantalizing perspective.

What 4th Wall? Pardon the crashing sound — it’s merely the fourth wall being broken as we begin our discussion on a philosophy-themed exploration of everyone’s favorite Merc with a Mouth, Deadpool. This journey takes us from the cinematic universe to the dusty annals of the philosophical world, where we introduce Wade Wilson, aka Deadpool, to a group of toga-clad gentlemen, the ancient skeptic philosophers. And trust us, they have a lot more in common than you might think. Think Deadpool, and your mind races to irreverent humor, gratuitous violence, sharp-witted banter, and a red and black spandex suit. But, hidden behind those masked eyes and the myriad bullet casings, lies an unexpected sage whose actions and attitudes bear a striking resemblance to the principles of skeptic philosophy. Philosophy? Deadpool? Yes, we’ve just gone there.

History lesson (yawn!): Let’s pause for a moment to brush up on our ancient history. Skeptic philosophy, born in the Hellenistic age around the 3rd century BC, focused on the idea of doubt and questioning. The skeptics, with Pyrrho as their founding father and Sextus Empiricus as their later torchbearer, were famous for their belief in “epoché,” or suspension of judgment. They held the radical notion that certainty was an impossible goal. Their philosophy taught that we should remain indifferent to ideas of good and evil and that our best hope lies in achieving a state of tranquil suspension of belief.

2. “From Togas to Spandex: A Brief Introduction to Skepticism”

Deadpool as TEACHER?: Deadpool, AKA Wade Wilson (Ryan Reynolds’ finest, and perhaps most self-referential role), seems to have been tutored not by Professor X but by Sextus Empiricus, the second-century AD Greco-Roman physician and philosopher, whose Pyrrhonian Skepticism philosophy is echoed in Deadpool’s irreverent dialogue and devil-may-care actions. The ancient School of Skepticism held to several core beliefs that he embodies:

Suspension of Judgment (Epoché): One of the main tenets of skepticism is the belief that one should suspend judgment due to the inherent limitations of our senses and intellect. Skeptics believed that we cannot gain absolute certainty about the nature of reality, therefore, it’s best to refrain from forming definitive beliefs. Unlike other philosophical schools that sought concrete answers, the skeptics believed that truth was subjective and elusive. They centered their beliefs on challenging dogmas and questioning widely accepted ideals. How meta is that? Marvel’s Kevin Feige has been plagiarizing the Skeptics! Who knew?!?!

Equipollence (Isostheneia): This concept refers to the equal strength of opposing arguments. Skeptics held that for every argument, there is an equally plausible counter-argument. This balance, or equipollence, further justifies the suspension of judgment. This is why Deadpool has a comeback for everything :-)

The Absence of Absolute Truth: A fundamental tenet of Skepticism was the belief that absolute truth does not exist. They asserted that what we perceive as reality is inherently flawed, and our interpretations of the world are rife with biases and inaccuracies. Meaning wrapped in riddles locked up in puzzles is how a Skeptic perceives the world. That explains the dialogue of the films a bit now that I understand that!

Indeterminacy (Acatalepsia): This principle asserts the idea that human understanding is incapable of comprehending the nature of things in their actuality. Thus, knowledge, in the ultimate sense, is indeterminable. Um… yeah — OK.

Tranquility (Ataraxia): A significant goal of the skeptic philosophy was to achieve a state of tranquility or peace of mind. Sceptics believed that by suspending judgment and accepting uncertainty, one could attain a sense of calmness, free from the disturbance of dogmatic beliefs. Wade Wilson isn’t exactly tranquil: but hey, no one’s perfect right?

Judgey much? Sextus Empiricus, the skeptic philosopher, believed in the idea of withholding judgment. To him, certainty was impossible, and the most we can hope for is a state of “suspended judgment.” Now, let’s consider our favorite mouthy mercenary. Deadpool’s constantly joking, rarely serious, and always unsure about what he’s doing or why he’s doing it. Is he a hero? A villain? An anti-hero? He’s constantly leaving us, and perhaps even himself, in a state of suspended judgment. And let’s not even get started on the ambiguity of his decisions. In Deadpool 2, he’s equally likely to save a kid as he is to sign up for a free cheese pizza.

I’m just not sure! At the core of skeptic philosophy lies the principle of uncertainty. The skeptics, notably Sextus Empiricus, a 2nd century AD philosopher and physician, preached a life of withholding judgment. They emphasized that the quest for certain knowledge was both impossible and unnecessary.

Looking through this lens, let’s observe our anti-hero. Deadpool’s character, remarkably portrayed by Ryan Reynolds, is a farrago of contradictions. Hero? Villain? Anti-hero? Wade himself seems unsure of where he fits. Even his motivations are shrouded in mystery. One moment he’s saving the world, the next he’s causing mayhem, and the next, he’s taking a detour for a churro. Through this state of constant ambiguity and suspended judgment, Deadpool personifies the skeptic principle of uncertainty.

Question Everything — Get your rules off me! The skeptics always questioned every assertion, theory, and belief. Similarly, Deadpool, with his irreverence and constant jest, challenges all notions of conventional superherodom. Nothing is sacred. From breaking the fourth wall to make a jab at the X-Men franchise to commenting on his own (Ryan Reynolds’) past cinematic blunders (cough Green Lantern cough), Deadpool turns skeptic philosophy into an art form, pushing the boundaries of comic book narrative conventions. The skeptics took pride in being the doubters of the philosophical world. They questioned every theory, every belief, relentlessly. If Sextus Empiricus were alive today, he’d likely applaud Deadpool’s relentless mocking and questioning of every superhero trope that has come to be regarded as gospel in our culture.

Acceptance of Paradox: Scepticism embraces the inherent contradictions and paradoxes of life. If there were a contest for embracing paradox, Deadpool would take home the gold. He’s a disfigured mercenary who’s also a romantic. He’s got a sharp wit but seldom a clear purpose. He’s the superhero who’s often the antihero. He straddles the line between life and death, humor and pain, pretty much embodying a paradox in a spandex suit. And in doing so, he’s teaching us a crucial skeptic lesson: life is full of contradictions, and that’s just fine.

Ryan Reynolds’ Deadpool is not only a unique cinematic delight but also a pseudo-philosophical guide to skeptic philosophy. Underneath the wisecracks, the cheeky comic-book references, and the ever-flowing banter, Deadpool, with his uncertainty, his endless questioning, and his embrace of paradox, teaches us to be comfortable with the ambiguity of life, a tenet that would make even Sextus Empiricus proud.

3. The Fantastic Four of Philosophy: Stoics, Epicureans, Skeptics & Cynics

So where does Skepticism fit in the pantheon of Greek philosophy? Well, Skepticism finds its place among four major schools of thought in ancient Greek philosophy: the Stoics, Epicureans, Skeptics, and Cynics. Each of these philosophical schools had its own distinct beliefs and principles. Let’s take a brief look at each:

  1. Stoicism: Emphasizes the importance of logic, virtue, and inner strength in achieving personal fulfillment and tranquility. Stoics believe in aligning one’s life with the natural order of the universe to attain peace of mind.

  2. Epicureanism: Advocates for the pursuit of pleasure as the highest good, with an emphasis on the pleasures of the mind and limited desires. Epicureans strive to achieve a harmonious state of ataraxia — ultimate relaxation and freedom from fear.

  3. Skepticism: holds doubt and suspended judgment at its core. Skeptics, as mentioned earlier, do not attempt to seek certain knowledge, believing it is both impossible and unnecessary. Instead, they celebrate uncertainty and embrace paradox in life.

  4. Cynicism: Promotes a rejection of conventional values, societal norms, and materialistic pursuits. Cynics seek to live a simple life, focused on self-sufficiency and virtue.

No-one ever accused Deadpool of being a slacker: MAXIMUM EFFORT!!!!!

4. Deadpool & Diogenes Walk into a Bar

If Deadpool and Diogenes were hanging out in a bar today, what would they talk about? What would they agree on? Well, chances are, they’d bond over their shared love for pushing boundaries, questioning norms, and poking fun at the world around them. Both Deadpool and Diogenes thrive in dishing out satirical commentary laced with humor while challenging societal expectations in their own unique ways. Their conversation might play out something like this:

  1. Irreverence: Deadpool and Diogenes would boast about their irreverent approach to life, mocking the established ideals and norms. This commonality would provide a solid ground for mutual admiration.

  2. Challenging Authority: Fueled by their penchant for questioning authority and rules imposed by the world, these two would revel in their disregard for the status quo, comparing notes on their respective.

  3. Mouthy Merc: We all know Deadpool as a mouth on him… and Diogenes wasn’t one to hold his tongue either. These big talkers would tout their wit, trading jabs, and insults, and perhaps engaging in a friendly battle of wits. They’d likely appreciate each other’s provocative nature and ability to push conversational boundaries.

  4. Embracing Paradox: As Deadpool and Diogenes share their stories, they’d undoubtedly recognize their shared affinity for embracing the paradoxical aspects of life. Both refusing to fit neatly into established categories and stereotypes, they’d find camaraderie in their shared unconventional existence.

  5. Breaking the Fourth Wall: Though Diogenes lived in a time when the fourth wall wasn’t a cinematic concept, he might appreciate Deadpool’s unique ability to address the audience directly, challenging the status quo of storytelling and expectations within the medium. This shared tendency to break conventions and disrupt normative boundaries would further solidify their connection as free-spirited thinkers.

  6. Laughing at Life’s Absurdity: Indisputably, both Deadpool and Diogenes share a playful yet incisive sense of humor. Their banter at the bar would likely be punctuated by chuckles and laughter as they discuss the various absurdities and follies of human nature and life itself.

  7. Disregard for Appearances: Finally, Deadpool and Diogenes would almost certainly bond over their shared disregard for appearances. With his disfigured looks and skintight suit, Deadpool defies what it means to be a traditional action hero. Similarly, Diogenes lived in a tub, in ragged clothing, directly challenging societal expectations and standards of appearance. Together, they’d celebrate this defiance, encouraging each other to stay true to themselves, irrespective of how the world perceives them.

The unanswered question? Which one is going to keel over off their bar stool first? My bet is that Deadpool will win that one :-).

5. Skepticism in Spandex: How to Succeed in Life, Deadpool Style

So, with all this in mind, what can we learn from Deadpool’s embodiment of skeptic philosophy? Here are some lessons you might contemplate in your own life:

  1. Embrace Doubt: Allow yourself to recognize the limits of human knowledge and embrace uncertainty and doubt. This can lead you to develop a flexible and open-minded approach to life.

  2. Revel in Paradox: Deadpool teaches us that life is full of contradictions and paradoxes, and attempting to make sense of everything can be overwhelming. Instead, enjoy the absurdity of the imperfect world we live in, and be comfortable embracing these complexities.

  3. Question Authority: Never swallow everything you hear or read without question. Be inquisitive. Challenge the status quo and the beliefs that have been handed down to you. Instead, develop your own critical thinking skills and evaluate ideas and information presented to you.

  4. Laugh at Yourself and the World: Humor is a powerful way to cope with life’s absurdities and setbacks. Deadpool shows us that laughter can be an effective tool in dealing with challenges and finding peace within our existence.

  5. Stand Up for Your Beliefs: While focusing on skepticism and doubt, Deadpool also reminds us that standing up for our values and beliefs is essential. Be willing to speak up and challenge popular opinions when necessary.

  6. Push Boundaries and Shatter Expectations: Deadpool isn’t interested in fitting into anyone else’s mold. Be unapologetically yourself, and don’t be afraid to defy societal expectations and conventions. Forge your own path and embrace your uniqueness.

  7. Cultivate Resilience: Life can throw curveballs at us, but like Deadpool, we can learn to face adversity head-on and bounce back from setbacks. Cultivate resilience by developing a strong support system, learning from your experiences, and maintaining a sense of humor in the face of challenges. Just as Deadpool continually bounces back from adversity and seemingly insurmountable challenges, we too can cultivate resilience in the face of life’s setbacks. Keep moving forward and adapt to the ever-changing circumstances that life throws at you.

Maximum effort!!: As you incorporate these Deadpool-inspired lessons into your life, always remember to put forth MAXIMUM EFFORT!!!. With determination, passion, and a bit of irreverent humor, you’ll find yourself embracing a more exciting, fulfilling, and, ultimately, meaningful life experience. Just like Deadpool and Diogenes, be fearless in poking fun at the world, questioning norms, and challenging accepted wisdom — all while enjoying the wild ride that is life itself, spandex optional. Thanks for reading, Ken


About me: I’m a software engineer by training and a software leader by profession. I’ve led two California-based SaaS companies as CEO, and am now back in my home country Australia. I’m passionate about tech & product & believe product management is the highest leverage activity a CEO can participate in. I’m here on Medium writing mostly long-form posts on topics I’ve got experience in, like #Leadership #Fundraising #Investing #SaaS, #Product, #Startups, #Offshoring. I’m on LinkedIn regularly — feel free to connect with me at

Shaw Investments: You can also learn more about what I get up to at or submit a financing proposal to us for consideration. We are early-stage tech investors, usually investing in companies with between $100k and $1M in ARR. We also invest in commercial real-estate. Reach out to me on

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