Exploring the Dark Side: Intriguing Podcasts on Infamous Figures
From notorious despots to icons of media madness, this collection of podcasts delves into the tangled narratives of some of history’s most feared and sometimes misunderstood individuals. If you have an interest in true crime, popular culture, philosophy, or political drama, discover these ten exceptional podcasts that offer a comprehensive examination of humanity’s darker aspects.
Behind the Bastards

Hosted by Robert Evans, a journalist rather than the filmmaker, Behind the Bastards investigates some of the vilest characters throughout history, encompassing a range from ruthless dictators to contemporary scammers and cult figures. Each episode is extensive and provides an in-depth exploration of a topic, occasionally spanning multiple episodes. A notable starting point is the compelling series focused on Vince McMahon. With each installment, Evans, along with a guest, intertwines thorough historical insights with sharp humor and an underlying sense of indignation. It’s a blend of the darkly amusing and the educational.
Behind the Insurrections

A spin-off of Behind the Bastards, also led by Robert Evans, Behind the Insurrections is a limited series that examines the history of events involving both foiled and successful revolts worldwide, including notable antifascist movements. Joining him is Propaganda, his co-host from Hood Politics. With their signature blend of humor and astute observations, they draw alarming parallels between historical uprisings and current threats to democratic structures. The familiarity of the situations discussed is unsettling. Start with “Mussolini’s March on Rome: The First Fascist Insurrection” for an insightful introduction.
Weird Little Guys

On Weird Little Guys, Molly Conger explores her specialty: the not-so-great personalities who are fundamentally just oddballs. Each episode showcases dubious historical and cultural figures you may not have encountered before. The format feels akin to receiving intriguing anecdotes from an erudite friend, repeating that even when the topics are heavy, the presentation remains insightful and light. Understanding how certain extremists became infamous is a strangely therapeutic experience.
This Guy Sucked

Host Claire Aubin navigates the murky waters of history on This Guy Sucked, where she critically analyzes dreadful male figures within our past and present, including topics ranging from Voltaire to mid-century liberalism. Engaging in dialogues with historians and other scholars, the podcast is both comical and informative. Aubin elevates this exploration beyond standard recounting, sparking meaningful discussions while correcting misconceptions learned in previous lessons.
Bad Gays

Bad Gays, hosted by Huw Lemmey and Ben Miller, casts a spotlight on rogue characters from the LGBTQ+ sphere. Each episode is rich with engaging narratives blended with humor and academic scrutiny. The discussions challenge oversimplified narratives while posing significant inquiries about power structures, identity, and complicity. A great starting point is the episode on “J. Edgar Hoover,” which dissects this notable queer figure with depth and wit.
Real Dictators

Real Dictators is a captivating narrative history podcast that dives into the lives of some of the most notorious authoritarian leaders. Hosted by Paul McGann, the show merges storytelling with historical accounts, enhanced by rich soundscapes and dramatic pacing that evoke a cinematic experience. Each season or special segment revolves around a specific dictator—think of figures like Stalin, Mao, or Saddam Hussein—exploring their rise to power, ideological principles, and oppressive regimes.
The Villain Was Right

In The Villain Was Right, comedians Craig Fay and Rebecca Reeds humorously defend cinematic villains, challenging the audience to consider, “Were they really in the wrong?” With sharp wit and unexpected arguments, they change the lens through which you view popular films—like the motives of characters from The Devil Wears Prada. Instead of focusing solely on historical tyrants, the podcast brings attention to lesser-known antagonists, such as the Wet Bandits from Home Alone, making for a compelling introduction to the series.
Disgraceland

On Disgraceland, Jake Brennan intertwines true crime tales with the music industry, uncovering stories of musicians who have led notoriety-fueled lives. The high-quality production enhances the captivating narration, making it seem almost theatrical. Imagine if Behind the Music were set against a backdrop of scandal—this podcast executes that perfectly.
Evil Genius with Russell Kane

On Evil Genius, comedian Russell Kane leads lively discussions with guests about whether historically significant figures were genuinely malicious or simply complex individuals. It combines elements of history and gaming in a refreshing format. Since Kane’s comedic background is central to the style, expect humor to accompany the lessons. Episodes are brisk and manage to delve into moral ambiguities without becoming didactic, and a great starting point is the episode on Walt Disney, a figure often idolized yet deserving of nuanced evaluation.
Very Bad Wizards

On Very Bad Wizards, philosopher Tamler Sommers and psychologist David Pizarro engage in discussions about morality as it pertains to the behavior of bad actors in culture, cinema, and everyday life. The podcast is both enjoyable and philosophical, inviting listeners to explore profound topics casually. With Sommers’ biting wit and Pizarro’s informed perspectives, their dynamic chemistry drives humorous commentary while tackling complex ethical questions.