20 Photos Of History’s Most Evil Men Looking Super Chill

Imagine Darth Vader cracking a smile under his helmet, or Lord Voldemort relaxing on a sun lounger. Weirded out? You should be. After all, there’s just something seriously creepy about bad guys taking it easy. The same is true of history’s real villains – watching men responsible for the deaths of thousands or even millions enjoy themselves and chill out is as disarming as it comes. However, these 20 photos show some of history’s most evil or feared men doing just that.

20. Kim Jong-un

Just because you’re the dictator of an oppressive regime, it doesn’t mean you can’t have fun. At least, that’s what this photo of Kim Jong-Il’s son and successor, Kim Jong-un, seems to suggest. Indeed, the current North Korean leader, who has continued the Kim Dynasty since 2011, is pictured enjoying himself on a rollercoaster – while many of his country’s people toil away in labor camps.

19. Adolf Hitler

In this rare color photograph, Adolf Hitler – leader of the German Nazi Party and perhaps the most widely recognized embodiment of evil the world has ever seen – slumps into a comfy armchair, a smile on his face. It’s an image that certainly shows a deep contrast with the atrocities committed by Hitler in World War II. Taken by the dictator’s personal photographer, Hugo Jaeger, the picture didn’t see the light of day until 1965 – 20 years after Hitler’s death.

Image: via reddit/crabtheseeker

18. Joseph Stalin

As leader of the U.S.S.R, Joseph Stalin infamously oversaw a regime that led to millions of deaths. But here, he looks like a playful child. The disparity is certainly unnerving. Indeed, it’s almost unbelievable that someone responsible for such brutality to occur would also have a sense of humor.

Image: via xinhuanet

17. Mao Zedong


Chairman Mao’s disastrous reign over China is regarded as the worst throughout all of recorded history in terms of the number of deaths. In fact, anywhere from 40 to 70 million people are thought to have lost their lives under his rule. However, in this photo, the authoritarian leader doesn’t seem to have a care in the world as he relaxes by a picturesque lake.

Image: via Le Mur de Laine de Briques

16. Kim Jong-il

During his reign as Supreme Leader of North Korea, Kim Jong-il maintained his cult of personality with propaganda that painted him as a deity. He probably wasn’t too happy, then, when this photo saw the light of day. Indeed, sat in just his briefs, the dictator looks a shell of the man he claimed to be.

Image: via The Underground

15. Osama bin Laden


Prior to forming al-Qaeda, terrorist leader Osama bin Laden was apparently keen on martial arts. But no matter how mundane or humanizing such photographs may appear, there’s no forgetting the atrocities committed by the man behind the 9/11 attacks. In fact, the FBI was so determined to bring Bin Laden to justice that they offered a $25 million reward for his capture before his death in 2011.

Image: Hulton Archive/Getty Images

14. Benito Mussolini

If you saw this picture out of context, you probably wouldn’t believe that it was of the man who took Italy into World War II on the side of the Nazis. Indeed, Benito Mussolini looks totally chilled out as he rides his motorcycle around his villa. In reality, of course, the head of the National Fascist Party was a dictator who stripped away the rights of his people before heading into a losing battle.


13. Idi Amin

Idi Amin only ruled as Uganda’s president for eight years, from 1971 to 1979. And yet, he still managed to commit all manner of horrific human rights abuses that resulted in hundreds of thousands of deaths. However, his legacy of destruction appears not to be troubling him here as he relaxes in a sun lounger.

Image: via Gulagbound

12. Adolf Hitler

Before he enlisted in the army and ultimately moved into politics, Adolf Hitler was a budding artist living in Vienna, Austria. And it’s easy to believe that, had he not been rejected from art school twice, his life might have turned out very differently. Indeed, pictured here with dog Blondi, the future warmonger looks decidedly chill.

Image: Reuters via Lidovky

11. Kim Il-sung


As leader of North Korea from 1942 to 1994, Kim Il-sung started the now three-generation strong Kim Dynasty. And at first, the country’s close relations with the Soviet Union led to years of prosperity – if not democratic freedom – for its people. However, the country ultimately sank into a wave of famine and poverty. As a young man, of course, there was no way Kim could foresee that – which probably explains his smiling family portrait here.

Image: via iFunny/TheWeebOfMemes

10. Vladimir Lenin

Dressed down and stroking a cat, it’s difficult to believe that this is Vladimir Lenin, the man who formed the Soviet Union under the Communist Party. While the former Marxist’s legacy is controversial and it might be harsh to class him as “evil,” there’s no denying the political oppression and death that took place under his regime.

Image: via Widelec

9. Joseph Goebbels


Two years before Adolf Hitler came to power, he served as best man at future Nazi Propaganda Minister Joseph Goebbels’ wedding. In the photo above, taken in 1931, Goebbels can be seen laughing and smiling with Hitler lurking just behind him. Indeed, the normalcy of this photo is almost chilling with the knowledge of what was to come.

Image: Baron/Getty Images

8. Francisco Franco

After overthrowing the republic in the Spanish Civil War, Francisco Franco then established himself as dictator of the country right up to his death in 1975. But seeing him here on the deck of a yacht, you’d hardly know he was responsible for the deaths of thousands of people under a totalitarian regime.

Image: AFP/Getty Images

7. Uday Hussein


The first-born son of Iraqi tyrant Saddam Hussein was apparently too evil even for his father’s tastes. But you wouldn’t know it from this candid photograph, found just weeks before Uday was killed by U.S. troops. Taken at one of his palaces, the picture shows Uday looking surprisingly chilled out for a man who supposedly reveled in murder, torture and rape.

6. Tsar Nicholas II

The man who dragged Russia into World War I – leading to more than three million Russian deaths, not to mention the rise of Communism – was seemingly no stranger to fun. Pictured here in 1899, five years after he came to power as the final Emperor of Russia, Tsar Nicholas II fools around with a friend in an idyllic garden.

Image: via The Atlantic

5. Kim Jong-un


In 2013, North Korea’s current leader Kim Jong-un was included at number 46 on the “World’s Most Powerful People” list by Forbes. Indeed, the photograph here showing him sharing a laugh with military leaders certainly gives that impression. After all, according to the South Korean defense ministry, Kim is capable of testing and launching nuclear warheads “at any time.”

Image: via rtvslo

4. Idi Amin

While in power, Idi Amin bestowed himself with various titles, including Field Marshal and Conqueror of the British Empire. In fact, Radio Uganda eventually declared him as, “His Excellency President for Life, Field Marshal Alhaji Dr. Idi Amin Dada, VC, DSO, MC, CBE.” Judging by this photograph, we wouldn’t be surprised if he also added “wild animal tamer” to that list.

Image: via JNSM

3. Osama bin Laden


Chances are, you won’t recognize Osama bin Laden in this family photo, taken in Sweden in 1971. As a teenager, he’s certainly a long way off the images that circulated on media channels after the 9/11 attacks. But that is in fact him in the green shirt and blue pants, second from the right. At the time, the future terrorist leader was described as “quiet” and “didn’t really stand out from the crowd.”

2. Kim Jong-il

Following in his father’s footsteps, Kim Jong-il took a “military-first” approach to governing the People’s Republic of Korea from 1994 to 2011. And no matter how cool he thought he looked in those shades, there’s no getting away from his abhorrent human rights record. Indeed, a 2004 report labeled Kim’s North Korea as “among the world’s most repressive governments.”

Image: via Zuruck/Watson

1. Joseph Stalin


Never let it be said that Joseph Stalin wasn’t a family man. As a matter of fact, pictured here with his daughter Svetlana Alliluyeva in 1935, the Soviet leader almost looks like any normal father. He wasn’t, of course: instead, he was the man whose leadership saw millions of people murdered or imprisoned in concentration camps, labeled “enemies of the working class.