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Diogenes of Sinope, the Cynic Philosopher

Diogenes (1882)
by John William Waterhouse
  • Alias: Diogenes of Sinope
  • Gender: Male
  • Race: Human
  • Occupation: Philosopher, Cynic
  • Religion: Not religious, skeptical of traditional beliefs
  • Allies: N/A (Diogenes often lived a solitary life)
  • Enemies: Hypocrites, pretenders, and those who upheld societal norms without critical examination
  • Abode/Base of operations: Athens, Greece (primarily lived in a barrel in the marketplace)
  • Nationality: Greek
  • Languages: Greek
  • Alignment: Chaotic Neutral
  • Affiliation(s): None in particular, though he associated himself with the philosophical school of Cynicism
  • Significant others: N/A (Diogenes was known to be unmarried and focused on his philosophical pursuits)

Diogenes, the enigmatic philosopher of ancient Greece, challenges the norms of society and leads a life of radical simplicity. Known for his unyielding pursuit of truth and his rejection of material possessions, Diogenes embodies the essence of philosophical rebellion.

With a rugged appearance and a sharp wit, he wanders the streets, engaging in philosophical debates and exposing the hypocrisy of those around him. Diogenes believes that societal conventions and artificial desires have clouded the path to genuine happiness and wisdom.

He strives to live in harmony with nature, seeking to free himself from the trappings of societal norms and social expectations. Diogenes questions the value of wealth, fame, and power, instead placing emphasis on inner virtue and self-mastery. He challenges individuals to examine their own lives and reassess their priorities.

Diogenes finds solace in the simplicity of his existence, owning nothing more than a cloak and a wooden staff. He eschews the trappings of luxury, living in a barrel in the marketplace of Athens. Through his intentional renunciation of material comforts, he demonstrates the power of detachment and the freedom that comes with it.

His actions and lifestyle are not mere eccentricities, but deliberate choices intended to provoke thought and challenge the status quo. By embracing a minimalist lifestyle and questioning the validity of societal norms, he seeks to inspire others to question their own lives and find meaning in simplicity and self-examination.

While some dismiss him as a madman, Diogenes sees himself as a beacon of truth in a world clouded by illusion. His wit and sharp tongue are weapons he wields against hypocrisy and pretense, exposing the contradictions in people’s words and actions.

Diogenes’s ultimate goal is to challenge conventional wisdom, provoke critical thinking, and lead others towards a more authentic and enlightened existence. Through his unconventional lifestyle and uncompromising pursuit of truth, he seeks to ignite a spark of self-reflection in the hearts and minds of those he encounters, encouraging them to embark on their own philosophical journeys.

Diogenes, the Cynic Philosopher

Medium humanoid (human), chaotic neutral

Armor Class 15 (unarmored defense)
Hit Points 85 (10d8 + 40)
Speed 30 ft.


Saving Throws Con +7, Wis +9
Skills Insight +9, Perception +9
Senses passive Perception 19
Languages Common, Ancient Greek
Challenge 6 (2,300 XP)

Background: Philosopher. Proficiency in Insight and Persuasion.

Unarmored Defense. While not wearing armor, Diogenes’ AC includes his Wisdom modifier.


Staff. Melee Weapon Attack: +6 to hit, reach 5 ft., one target. Hit: 8 (1d6 + 4) bludgeoning damage.

Cynical Retort (Recharge 5-6). He makes a cutting remark that undermines the target’s confidence. The target must make a DC 15 Wisdom saving throw or be afflicted with disadvantage on their next attack roll or ability check.

Lamp of Wisdom. He holds his famous lamp, symbolizing his search for an honest person. While holding the lamp, he has advantage on Wisdom (Perception) checks to detect deception and hidden objects.

Legendary Actions

Diogenes can take 3 legendary actions, choosing from the options below. He can take only one legendary action at a time and only at the end of another creature’s turn. He regains spent legendary actions at the start of his turn.

Insightful Observation. Diogenes closely observes a creature, gaining advantage on his next Wisdom (Insight) check against that creature.

Cynic’s Wisdom. Diogenes imparts a piece of his philosophical wisdom to an ally, granting them advantage on their next Wisdom saving throw.

Provocative Taunt. Diogenes mocks a creature, distracting it. The target must make a DC 15 Wisdom saving throw or have disadvantage on its next attack roll.


  • Tattered robes
  • Wooden staff
  • Lamp
  • A small bag of mixed nuts and seeds
  • A journal filled with philosophical musings


Cynical Dissent. Diogenes is known for his relentless skepticism and mockery of societal conventions. He is quick to challenge authority and question traditions.

Philosophical Wisdom. Diogenes is a wise and insightful philosopher, offering profound perspectives on life and virtue. He seeks to live in accordance with nature and encourages others to question their own beliefs.


Diogenes’ lair is a humble barrel located in the bustling marketplace of Athens. The barrel serves as his living quarters and study, and it is adorned with various philosophical texts and trinkets. Surrounding the lair are curious onlookers and followers eager to engage in philosophical debates.

Plot Hooks

  • Diogenes encounters a wealthy noble who scoffs at his simplistic lifestyle. He challenges the players to prove that true happiness does not rely on material wealth, leading to a series of tests and philosophical debates. As they navigate this journey, they explore the dichotomy between luxury and simplicity, and learn valuable lessons about the nature of contentment.
  • Diogenes becomes embroiled in a political conspiracy when he uncovers corruption within the city’s ruling class. He enlists the players’ help in exposing the truth and restoring justice, putting them at odds with powerful adversaries. Together, they navigate the intricacies of political intrigue, gathering evidence, and rallying support for their cause, all while staying true to their philosophical principles.
  • Diogenes stages a provocative performance in the city square, urging the players to join him in challenging societal norms and questioning the superficiality of social status. This attracts both admiration and scorn, creating a conflict that tests the players’ resolve. They must navigate the repercussions of their actions, standing up against societal expectations and embracing the freedom to live authentically.
  • Diogenes believes that virtue and wisdom can be found in the simplicity of nature. He leads the players on a wilderness retreat, guiding them to connect with the natural world and discover profound truths about themselves. As they explore remote landscapes, they encounter mystical creatures, hidden treasures, and engage in deep philosophical discussions under the starry sky.
  • Diogenes becomes the target of a group of philosophers who see his unorthodox methods as a threat to their own authority. The players must defend him against their attacks and unravel the conspiracy behind their motives. In this battle of wits, they delve into ancient philosophical texts, challenge traditional norms, and fight to preserve the freedom of thought.
  • Diogenes encounters a lost soul plagued by existential angst and offers guidance to help them find purpose and meaning in life. The players become instrumental in this transformative journey, navigating philosophical quandaries and aiding the troubled individual. Along the way, they explore the concepts of identity, self-discovery, and the pursuit of a fulfilling existence.
  • Diogenes discovers a hidden society of mystics who possess ancient knowledge. He seeks the players’ assistance in gaining access to their teachings, delving into esoteric rituals and deciphering cryptic texts. Together, they embark on a quest for enlightenment, unraveling enigmatic puzzles, and facing spiritual trials that test their commitment to the pursuit of truth.
  • Diogenes embarks on a pilgrimage to sacred sites, believing that the answers to life’s mysteries lie within these hallowed grounds. The players accompany him, encountering spiritual challenges and encountering divine manifestations along the way. Together, they delve into the realms of spirituality, exploring the nature of faith, and deepening their connection to the divine.
  • Diogenes is invited to participate in a prestigious philosophical debate, and he invites the players to join him as his allies. They must match wits with renowned scholars and win the argument using logic, rhetoric, and unconventional thinking. As they engage in intellectual battles, they explore various philosophical schools of thought, challenge established dogmas, and influence the course of philosophical discourse.
  • Diogenes unveils a hidden cache of ancient philosophical artifacts that hold immense power. He tasks the players with safeguarding these relics from those who would misuse them, embarking on a perilous quest to keep them out of the wrong hands. Along the way, they face formidable foes, unravel cryptic riddles, and make weighty decisions about the responsible use of knowledge and power.

Currently in the World

Diogenes is a middle-aged man with a scruffy beard, disheveled hair, and a weathered face that reflects a life of simplicity and contemplation. He is dressed in ragged clothing, consisting of a tattered cloak and worn-out sandals. Despite his unkempt appearance, there is an air of wisdom and defiance about him.

Currently, Diogenes is seated near his barrel in the marketplace of Athens. Surrounded by a bustling crowd, he observes the activities of the city with a mixture of curiosity and skepticism. His piercing gaze and thoughtful expression indicate that his mind is absorbed in deep philosophical contemplation.

The marketplace serves as Diogenes’ makeshift home and base of operations. The lively atmosphere and diverse individuals passing by provide him with a constant source of inspiration and material for his philosophical teachings. Surrounded by the noise of merchants, the chatter of people, and the scent of various goods, Diogenes finds solace in the midst of chaos.

His mood is one of tranquil contentment, as he has embraced a life of simplicity and renunciation of material possessions. He appears detached from the material world and finds joy in the pursuit of philosophical truth. Although he encounters skepticism, criticism, and occasional ridicule from passersby, Diogenes remains steadfast in his beliefs and unwavering in his pursuit of wisdom and virtue.

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