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One of the weird truths of living in an Instagram age is that documenting and publishing life's stupider moments is not only accepted, but encouraged. A more cynical writer than myself would probably suggest that our recent obsession with selfies is about distraction. Like maybe if you post enough pictures of yourself having a good time, no one will notice the raging wildfire of desolation that's eating you from the inside out.

Personally, I'm an optimist. I assume Instagram is proof we're all having heaps of fun all the time. Especially when you realize history's most important and serious figures also enjoyed getting the camera out to document goofy faces and stupid antics. We're all freaking children, all of us.

JFK Jr. in a Sweet Dress

John F. Kennedy Presidential Library

Remember when Sasha and Malia Obama took a picture of themselves at the inauguration and we were all so charmed by their adorable normalness that we made commemorative Sasha and Malia plates that we've been selling on the Home Shopping Network ever since? Remember that time? No? Weird, because I do.

Unlike the Obamas and Chelsea Clinton and George W. Bush's "art," John F. Kennedy's children never had the luxury of slowly easing into public life; Caroline and JFK Jr. were 3 and "just born" when they moved into the White House. And because JFK knew the public was obsessed with his family, the White House photographer had unprecedented access to the Kennedy kids, even when they went to a Hyannis Port beach and dressed their toddler son in a fish-splattered muumuu probably borrowed from a tiny Florida grandmother.

John F. Kennedy Presidential Library
I speak for all of us when I say, "Can you EVEN?"

For those of you too young to remember him before his 1999 death, John F. Kennedy Jr. grew up to be a lawyer, publisher, and owner of a Selleckian coif that made the panties drop:

Getty Images/Hulton Archive/Getty Images
You might say this shirtless picture of Kennedy made a "Splash" among the ladies! Or not say that!

Years before JFK Jr. was a heartthrob, before anyone started wondering about what Papa Joe did to earn the curse that was killing his boys, John F. Kennedy Jr. was just a boy who loved his sweet-ass fishy dress. Can you blame him?

Speaking of presidents' kids ...

FDR as You've Never Seen Him Before

Franklin D. Roosevelt Presidential Library

In 1924, 8-year-old John Roosevelt was missing his dad, so he sent him a letter. At this point in the conversation, there are two things worth mentioning: 1. John's dad was future president Franklin Delano Roosevelt, and 2. FDR had recently contracted polio and was getting state-of-the-art treatments in Georgia. Now, I'm guessing young John had no clue his daddy was away from home because his legs stopped working; he probably thought his dad was away doing political stuff, like governing the state of New York or cigarette-holder shopping, which makes John's letter all the more dickish:

Franklin D. Roosevelt Presidential Library
His first draft read "Dear Father, you are a 'murderer (of honesty!')"

John Roosevelt called out FDR for stealing his black pen, much like the wealthy would call him out for stealing their wages 10 years later. Which leads to at least a dozen questions: How precious of a commodity were black pens in 1924? Did John have to leave his shoe with a nanny to borrow the black pen that he used for this letter? Was FDR a chronic pen stealer, as John alleges, and if so, should we take his face off the dime? I vote "yes," but that's only because I haven't used dimes in three years.

After going the hell out of his way to demonstrate how whiny he's going to be during his teen years, John pulls a move that's half adorable and half psychopath-y. He draws a picture of his dad, heavily highlighting his father's ears and theeths.

Franklin D. Roosevelt Presidential Library
Translation: I'm sorry your legs aren't working. Here's a caricature of your most hilarious features as compensation.

The whole letter speaks highly of FDR as a parent; his son felt so comfortable with his father that he drew him as a living jack-o'-lantern, complete with Dumbo ears, an upside down light bulb for a body, and anorexic broomsticks for arms.

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The Russian Imperials Were Big Goofballs


Even if you've never taken a Russian history class or paid a street psychic to conjure the spirit of the Romanovs at a dinner party, you've probably seen the 1997 cartoon Anastasia. According to that movie, Rasputin was made of magic, the royal daughter Anastasia escaped execution, and everything turns out fine if you sing hard enough. The true history of the Romanovs was slightly grimmer.

Topical Press Agency/Hulton Archive/Getty Images
In real life, Rasputin was only half magic.

Thanks to the stiff-necked, hoity-toity looking photography of the time, we usually picture the Romanovs as grim-faced Victorians, but Russianer. Until the day they were murdered by the Bolsheviks, the Romanovs were actually a fun-loving group. And we've got the pictures to prove it. Here is Anastasia in her natural habitat, having fun with a camera and someone's dentures:

I'd like to think they're Rasputin's.

Anastasia's parents and aunts and uncles were even zanier. Here's a picture of her father, the future tsar of Russia, making monkey faces with his cousins, because apparently making faces was the only thing Russian imperials were good at.

You can't tell from the picture, but they're all farting here.

While I can't imagine the circumstances that compelled Russian royalty to capture their best simultaneous seizure faces, I really can't imagine a reason for a grown man to climb on another grown man's back and play airplane unless they've got a homosexual date going on later. But here it is: the future leader of Russia with a propeller in his mouth so you don't miss that this is, in fact, an approximation of a plane.

You can't tell from the picture, but Nicholas represents the landed aristocracy and the other person
represents Domodedovo International Airport runway.

Fidel Castro and His Castro Pretenders


After 50 years as the world's most stubborn and tangly bearded communist leader, Fidel Castro never struck anyone as a big goof. Between the fatigues and the constant presence of a cigar and his actual physical frame (he is 6'3"!), Castro struck an intimidating figure back in his prime. No wonder some of his facial hair refused to grow in certain patches of his face. Even his hairs were scared of him.

Keystone/Hulton Archive/Getty Images
Stare long enough and the bald spots look like angel wings.

But before Castro became the Castro who clung to his seat of power for 50 years, he was a divorced dad who just took over a little country. In 1959, Castro used a work trip to the United States to hang out with Fidelito, his third grade son, who was going to school in Queens. Not only did Fidelito meet up with his dad, but he brought a few school friends, who dressed up like Fidel Castro for the visit.

Those kids in the picture above aren't Cuban schoolchildren in a Cuban PR stunt hanging out with their Cuban president in a Cuban White House. These are red-blooded New Yorkers in fake beards and military caps, fawning over the biggest communist presence in the Western hemisphere. When asked about the visit later as adults, Fidelito's ex-school pals just thought their friend's dad was a cool army guy with a cool beard.

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Johnny Cash Sneaking Cake in the Bushes


Thanks to the movie and the countless story songs he wrote, we all know Johnny Cash's bio pretty well. He struggled with the demons of addiction and fire rings, he dressed in black as a reminder of all the people suffering in the world, and he's the only country artist everyone claims to respect or enjoy.

Dynamic Graphics/Creatas/Getty
"I hate country but I love Trisha Yearwood, I mean Johnny Cash."

But there's a secret about Johnny Cash that modern fans tend to overlook, forget, or simply not know: Johnny Cash was as dorky as he was badass. Yes, he played prison shows to provide entertainment to inmates, but he also traded puns on the cornball show Hee-Haw and hosted his own variety show for a year. The same guy who was once busted for smuggling drugs across the Mexican border later endorsed Taco Bell. (That one kind of makes sense, actually.) Do you know what doesn't make sense? "Chicken in Black," a god-awful Johnny Cash song about a man who has his brain implanted into a chicken. A CHICKEN.

Personally, I love the fact that this hard-living country outlaw was also a big dork. So this picture of Johnny Cash sitting criss-cross apple sauce in the bushes and eating a cake with his bare hands is pretty perfect. Yes, he's probably high as balls, which hopefully also explains why he's dressed like an old-timey railroad engineer, scarf and all. Either way, the fact that the man couldn't care less what you or I thought of him was what made him cool.

Picasso Dressed as Popeye

André Villers

By the time this picture was taken 1957, Pablo Picasso was 76 years old, stupid-rich from his art, and dripping with a trail of lovers so long that if you lined them up and cubed them, you could get to the moon and back. So it's not surprising that the man had more swagger than most in his old age. It's a liiiiiiiittle surprising that his bravado manifested itself in a prosthetic nose, a fake beard, a captain's hat, and smoking a comically oversized pipe. If your granddad walked out of his room looking like Popeye, you'd either call the home or ask if he's Johnny Depping it up for a big movie part.

Hold up -- Popeye doesn't even have a beard. What kind of crap was Picasso trying to pull anyway? Did we just get Picassoed?

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Gerald Ford Golfing With Men in Clown Pants

Gerald R. Ford Presidential Library

There must have been this moment when the entire decade of the '70s just said "Screw it" and started wearing actual vomit for clothes. Like everyone threw a raging kegger on December 31, 1969, laid out some fabric, threw up on the fabric, and then sewed that fabric into outfits for the upcoming 10 years.


Back then, people would host serious events and half the participants showed up looking like they just fell off the circus train. And that's how we ended up with this 1974 picture of President Ford playing golf with three congressmen we're going to call Representative Tablecloth, Senator Gunt, and Senator Flower Power. If you're anything like me, you probably did a double take on Senator Flower Power, because he looks a little like a Joker Dick Nixon.

On the other hand, you could pick up this incarnation of President Ford and plop him down at the 2014 Masters, and he'd fit right in. He'd probably be baffled by the lack of psychedelic vomit clothes, but give him a doobie, and he'd feel right at home.

John Wayne in Booty Shorts

Phil Stern

Adjust your peepers, fellas. This isn't a lascivious Girl Gone Wild shaking what her mama gave her at Padre. This is John Wayne, your grandma's favorite example of manliness and racist undertones.

Hulton Archive/Hulton Archive/Getty Images
Don't let the stank tooth fool you. John Wayne was definitely racist.

It turns out that moments of leisure in the '50s were opportunities for icons of virility to squeeze their moose knuckles into polyester Daisy Dukes.

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Stanley Kubrick Dancing and Butt Bumping His Sister

Quick survey: Have you ever met a film buff who didn't have a filmy hard-on for Stanley Kubrick? Probably not, because like a Stanley Kubrick movie that doesn't leave me brooding and uncomfortable in my own skin, they don't exist. From 2001: A Space Odyssey to Eyes Wide Shut, critics have always seen Stanley Kubrick as a serious artist who wasn't afraid to delve into the deepest corners of the human psyche, which makes this adorable picture of this little chubster dancing with his sister all the more endearing.



These two are trying their whitest to approximate the boogie dancing that was sweeping the nation at that very moment, or Barbara was actually a very lifelike wind-up doll and Stanley had the body awareness of a sack of mashed potatoes hopped up on Dr. Pepper. Which is why, in a moment of special exuberance, Stanley's big butt pushes his wind-up-doll sister to the ground. He didn't mean to do it. He just wanted to dance. Clearly, he meant no harm. Let's go back in time and say a quick prayer for these two: "Dear Jesus, please don't let this fun dance that led to mild violence sit in Stanley's head too long. Amen."

Hopefully that helped.

Kristi is a senior editor and columnist for Cracked. For more from her, check out past articles here and her Twitter page.

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