From infamous tyrants to modern media monsters, these podcasts explore the most messy, menacing, and sometimes misunderstood figures throughout history. Whether you’re into true crime, pop culture, philosophy, or political intrigue, here are 10 standout podcasts that dive deep into the dark side.
Behind the Bastards
Credit: ‘Behind the Bastards’
Hosted by Robert Evans (not the film guy, the journalist and former war correspondent,) Behind the Bastards is a deep dive into some of the worst people in history, from brutal dictators to modern-day grifters and cult leaders. Episodes are long and go extremely in depth. Evans will often take several episodes to cover a single subject. (Like his Vince McMahon series, which is incredible and a good place to start.) With every episode, he and a guest blend sharp historical research with biting humor and a little righteous rage. It’s dark, funny, and educational.
Behind the Insurrections
Credit: ‘Behind the Insurrections’
A spin-off of Behind the Bastards (and also hosted by Robert Evans), Behind the Insurrections is a limited series that looks at the history of attempted (and successful) insurrections around the world. (There’s a fun sprinkling about history’s antifascists, too.) Along with his friend and co-host Propaganda (from Hood Politics), Evans uses his signature wit and insight to draw chilling parallels between past uprisings and modern-day threats to democracy that feel both clarifying and terrifying. It’s shocking how familiar it all sounds. Start at the very beginning with “Mussolini’s March on Rome: The First Fascist Insurrection.”
Weird Little Guys
Credit: ‘Weird Little Guys’
On Weird Little Guys, Molly Conger leans into her niche expertise: terrible people who, deep down inside, are actually just messed up weirdos. In each episode, she profiles questionable characters from history, media, and myth whom you may or may not have heard of. I love that even if the subject matter is heavy or depressing, listening to this show feels like getting gossip from your smart, well-read friend. If you can’t do anything about skinheads, the least you can do is figure out how they got to be such huge losers. It’s cathartic.
This Guy Sucked
Credit: ‘This Guy Sucked’
Historian Claire Aubin is the host of This Guy Sucked, an academic takedown of awful men throughout history, culture, and current events, from Voltaire to mid-century liberals. Claire ups the ante with historians and professors for conversations that are equal parts funny and smart. This a history podcast with a great host who is doing more than just reading Wikipedia entries—she’s sparking engaging conversations and teaching you about some of the stuff you learned wrong the first time around.
Bad Gays
Credit: ‘Bad Gays’
Bad Gays, hosted by Huw Lemmey and Ben Miller, shines a light on villainous figures, but only the queer ones. Each episode is full of great storytelling, lots of jokes, and academic rigor. It challenges simplistic narratives and asks important questions about power, identity, and complicity, something that anyone on the gender spectrum can fall prey to. Start with “J. Edgar Hoover,” an episode about an iconic bad gay, dissected with nuance and wit.
Real Dictators
Credit: ‘Real Dictators’
Real Dictators is a gripping narrative history podcast that dives into the lives of some of the world’s most infamous authoritarian rulers. Hosted by Paul McGann (with a dramatic, cinematic tone), the show blends historical facts with the kind of immersive storytelling, dramatic narration, beautiful sound design, and compelling pacing that will make you feel like you’re at the movies. Each season or multi-part episode focuses on a different dictator—think Stalin, Mao, Saddam Hussein—tracing their rise to power, ideologies, and brutal regimes.
The Villain Was Right
Credit: ‘The Villain Was Right’
The Villain Was Right is a hilarious rewatch podcast that defends famous movie villains and asks, “Were they really that wrong?” Comedians Craig Fay and Rebecca Reeds bring episodes that are clever, irreverent, and surprisingly persuasive. You’ll never look at The Devil Wears Prada the same way again. We’re not talking about Stalin and Hitler, we’re talking about The Wet Bandits in Home Alone. (In fact, that’s a fun place to start.)
Disgraceland
Credit: ‘Disgraceland’
On Disgraceland, Jake Brennan combines true crime stories and the music world, to tell the stories of musicians who have gotten away with murder, if not literally then figuratively. The production level is high, Jake has an unforgettable voice that brings drama to every story, and the show is endlessly bingeable. Think Behind the Music behind bars.
Evil Genius with Russell Kane
Credit: ‘Evil Genius’
You’ll love the debates on Evil Genius, where host and comedian Russell Kane (and his guests) argue whether controversial historical figures were truly evil—or just complicated. It’s both history and game! Russell is a comedian, so this is for people who like their history with a dash of comedy. Episodes are fast-paced and dig into moral gray areas without getting preachy. Start with Walt Disney, a guy we all love but who also really needs a few minutes under the microscope.
Very Bad Wizards
Credit: ‘Very Bad Wizards’
On Very Bad Wizards, a philosopher (Tamler Sommers) and a psychologist (David Pizarro) talk about the morality of bad behavior in pop culture, film, and real life. It’s both entertaining and will send you down philosophical rabbit holes. You’ll love it because it’s both academic and insightful while still being casual and fun. Sommers brings the fiery, contrarian philosopher energy and Pizarro offers thoughtful, data-informed perspectives. They have great chemistry, and they’re not afraid to roast each other.
