This is certainly a bold claim – that of having collected the funniest, strangest, and downright silliest family portraits ever snapped. To be fair, we all have lovely memories spent with parents, siblings, and extended family. But sometimes, when we see actual evidence of those events, it’s enough to make us feel burning regret. Odd matching outfits, fighting kids, and some things that are difficult to describe… we have it all in this list. It’s time to get nostalgic, with a healthy helping of cringe!
The Most Hilarious Family Portraits Ever Taken
Mom Does It Best
We all love learning more about our family tree. But some people take the metaphorical term way too far. When this mother decided that stacking her family, one on top of each other, on a tree branch was a great idea, we are sure that the photographer was feeling rather sick. This is indeed a stomach-churning display of all too intimate familiarity. We love the large gap between the boys and their mother. Thank you for practicing social distancing…
Mom Does It Best
A Storm Cloud At The Beach
Not every girl wears a bikini to the phase. Some wear… whatever that studded trench coat thing is! Many of us had goth phases growing up, and that is completely alright. But just remember, kids, when you grow up and become a lawyer or a doctor, there will be plenty of evidence! This Marylin Manson-inspired getup brought an intense shadow to a beautiful, sunny day at the beach. Well, at least the other girls look they’re having fun, and we’re sure Miss Evanescence is too, deep, down inside.
A Storm Cloud At The Beach
Sickeningly Sweet
This family obviously spent a lot of money and time putting together their outfits together and coordinating this could-have-been beautiful family portrait. Unfortunately, it seems like little Mikey on the right indulged in one too many Double Stuf Oreos before the shoot and paid the price for it. It’s amazing how the photographer managed to capture the sickening moment so perfectly! Maybe he or she needs to think about becoming a sport or wildlife photographer.
Sickeningly Sweet
Performance Family Portraits
Some families aren’t satisfied with the mundane family portrait. They need to show the world that they are different. This family seems to be made up of Cirque du Soleil performers. We love the baby’s expression in this one. He has no idea what is happening, but he’s just going along with it. Sorry, kid, but you are going to have to endure a whole lot of weirdness growing up. Hopefully, he’ll join the family troupe when he’s old enough!
Performance Family Portraits
Carbon Copy
Some kids are sadly doomed to live in their parents’ shadows. As for this little girl, she seems to have become her mother. As creepy as this picture is, we can’t help but feel sorry for this kid. She never stood a chance of being her own person! She is incredibly adorable, however, and they do seem quite happy together. Even if a future serial killer is in the works… Those glasses are really cool, though!
Carbon Copy
Matilda In The Middle
Anyone that is the middle child will tell you that life has not been easy. Indeed, the stereotype of the middle child being the least loved seems to be coming to life in this hilarious family picture. This poor girl is so uncared for that her parents didn’t even care that she wasn’t even in the picture! That being said, maybe she is just camera shy and we’re just being mean. We’re sure that her parents love her very, very much.
Matilda In The Middle
Kings Of Cool
When was this picture taken, you may ask? We are not sure. Could be the 80s, or it could be far older than that. Either way, these three cool guys needed to let you know that, in case you hadn’t noticed, that they are seriously ‘COOOOOL’. Sometimes, loud outfits, mullets, and chunky shades aren’t enough. You need to literally remind people that you are cool. What do you think? Are these ‘bros’ cool or fools?
Kings Of Cool
Space Case
We are starting to strongly doubt whether these folks are from Earth. They just have such strong alien energy. It doesn’t help that their background is space, either, or that they are proudly displaying their poor cat’s freshly neutered business! Only aliens studying cats could be so happy about such a mundane process. We really feel sorry for this cat. Kitty obviously doesn’t have claws, otherwise, this couple would be in for it for such humiliation.
Space Case
Sexy Santa
For the love of children’s innocence, cover-up, woman! No one needs to see that, especially not children. While Mrs. Clause decided to bring out her festive boudoir for this disturbing family shoot, her husband is dressed like a Russian hitman from the 80s. It’s all rather polarizing and the inconsistency of their outfits is perhaps more disturbing than the latex and garter. Maybe it is time to call Child Protection Services? We certainly would not recover from seeing our moms this way…
Sexy Santa
Rainbow Love
Seeing a rainbow is generally a magical experience. But in this case, you might wish that a hurricane came out of nowhere. It’s a nice idea, that of turning your family members into the colors of the rainbow, to show the harmony and beauty of family life. Sadly, it didn’t work very well in execution. The dad looks like a giant piece of salmon sashimi while the mom looks like a titanic Cheeto. The kids are cute, though.
Rainbow Love
Slam Dunk
Pregnancy shoots are generally incredibly tender and emotive displays where soon-to-be parents celebrate their growing bundle of joy. Not in this case, however, as this loony fellow forced his wife into this ridiculous basketball joke! The mother-to-be obviously didn’t want her face in this one, and her posture seems tense and filled with cringe. Can you imagine the baby, once he or she is old enough to understand pictures, seeing what their father put them through before they were even born?
Slam Dunk
Dinner For Three
These casual, wine-sipping boys set up the ultimate cozy scene for themselves and their cat. The roaring fire, the white turtlenecks, and the slightly racist Native American-themed boots – all the ingredients for a perfect cringe party. Oh, and then there’s the cat, who seems to have its own turtleneck. It seems incredibly bewildered. At least the fondue seems yummy. Well, at least these strange guys know how to have fun. We certainly couldn’t host this well.
Dinner For Three
80s Horror
Now before you get too alarmed with this next shocking family portrait, you should know that it was done for laughs! This picture was taken recently, and it was meant to recreate that classic 80s cheese. We just feel sorry for the girls, as their hair needs some serious attention! A lot of effort went into making this priceless vision of horror and you have to give them points for it. Everyone came together to make this family portrait one for the books.
80s Horror
Mullets Incorporated
Unlike our previous joke family portrait, this one seems to be incredibly sincere. There was a time when mullets ruled the world, and we are very happy that the trashy hairstyle died. All that is left of it now is pictures like these. And what a picture it is! These are some of the most respectably powerful mullets we have ever seen. The boy isn’t even thirteen years old and he looks like he could drive a Ford Mustang GT off a cliff and live to tell the tale.
Mullets Incorporated
Got Her Goat
From mullets to goats, next up we have a rather pagan-looking family portrait where a witchy mother decided that a goat was needed to complete the ritual – uh, we mean, completely innocent family portrait. No goats were sacrificed to ensure that this baby would be born strong and healthy. We love that the goat got a flower crown and shawl, too! She must have felt like a princess, which is important, as she is probably the godmother. Goat-mother?
Got Her Goat
Upsetting Letters
It seems that these kids have a fierce aversion to letters, or joy. As soon as their parents put the letters in their hands, they began bawling! We cannot imagine what set them off, unless they experienced some particularly traumatic spelling lessons. Why is it that kids always choose the worst moments to begin performing? Either way, this otherwise adorable family portrait is going to take some time to pull off. Get these kids some chocolate milk!
Upsetting Letters
Throwback Thursdays
This family portrait might have been one of the first-ever taken, with one of the first cameras ever made, which was probably a daguerreotype camera. Pictured we have a severe-looking woman with a broom who was too cool to take her shades off, a mysterious cowboy that couldn’t shake his camera shyness, and his irritated-looking partner. Maybe the man was an outlaw who didn’t want to be identified? It’s good to see that men have always hated having their pictures taken!
Throwback Thursdays
Save Me
You might be wondering why this normal-looking family portrait was included in this list? Well, take a closer look at the mom in the bottom-middle of the picture! She has a worrying expression that says, ‘Save me!’ All jokes aside, some people do communicate their true feelings in a picture. After all, a picture says a thousand words. She probably just struggles to not look awkward in pictures. We wish them better luck in the next family portrait!
Save Me
Ghostly Kids
We love seeing happy little girls playing and doing their kiddy thing. This picture, however, has some rather unsettling elements, however. For starters, that black, gothic dress is very spooky. It’s like something out of a Victorian ghost story! Then there’s the position of her legs, compared to her upper body. It seems like it’s all wrong, as if she has been twisted around. Finish off with a ghostly old camera quality and you have a very scary snap.
Ghostly Kids
Bathroom Baby
Why… why would you surround your child with toilet plungers and spoil an otherwise delightful scene?! What kind of message are you trying to convey? We wonder whether this girl’s designated role is ‘toilet unblocker’. If you are into toilet plungers, then this picture might be right up your alley. At least this girl seems pleased with her lot in life. Good for her! We firmly believe that life is what you make of it.
Bathroom Baby
Lionesses
Welcome to the 80s jungle, where big hair reigned and hairspray cans were so commonly used that it is incredible that the ozone layer is still standing. Here we have a pair of fierce lionesses that are on the prowl. The hoop earrings are a nice touch, too. If you are old enough to have lived through the 80s and wore your hair like this, pat yourself on the back. You made it through one of the tackiest periods in human history.
Lionesses
Denim On Denim
Someone in this family came up with the ultimate family portrait idea. ‘Why don’t we all wear denim everything and then pile up on top of each other?’ Suggested one of the members. And they all agreed enthusiastically, going on their bright expressions. Even the edgy, Sinead O’Connor lookalike is having the time of her life. We would say that this family is Canadian, but given the sunny, tropical background, we have no idea anymore.
Denim On Denim
Cinematic Cringe
It might be a bit unfair going for low-hanging fruit like 80s family portraits, but they are just so ridiculous and bizarre that it’s hard not to. Here we have a perfect example of a traditional family mixing things up with their family portrait. The kids and their mother, with classic 80s mop haircuts, are powerfully encompassed by their father’s enormous head, who seems to be looking to the future, proudly. Keep staring on, papa.
Cinematic Cringe
The Problem Child
Every family has a member who refuses to conform, with this 80s family portrait showcasing a particularly fantastical little boy. We have no idea what that scary mask is supposed to be. It seems to be some kind of evil pilgrim. Either way, his parents could not get him to take it off, even for a family portrait. Not that they seem to mind too much, going on their smiles. Maybe they accepted this child for his individuality?
The Problem Child
Smothered
Finally, a family portrait that is wholesome, adorable, and sincerely hilarious! This cute little kid got overwhelmed by his parent’s smooches, and he does not feel like returning the love. In fact, he looks like it’s too much to handle! If you were lucky enough to have parents that weren’t scared to smother you in public, then you can certainly empathize with his fellow. He can certainly look forward to an affectionate and protective upbringing!
Smothered
The Shady Family
Now this family is not messing around. They all brought their shades to their family portrait. We can only guess that this was the dad’s idea, as he seems to think that he is too hot to handle, to the point that everyone needs to shield their eyes from his brilliance. The irony of this family portrait is that the park scene is a backdrop! We would also prefer it if these parents would show less skin. Yikes!
The Shady Family
The Alternate Dimension
We love it when families break the traditional mold. Here we have one that is multi-racial and doesn’t seem to have a set hierarchy. This looks more like a hilarious photo day at some office than a family portrait, but who are we to judge? The man in the picture is lucky to have so many strong and supportive women in his life, including the enormous one that follows them everywhere they go. Just kidding, it’s just a special effect.
The Alternate Dimension
The Ultimate Dudes
The 80s saw a very peculiar and horribly cringeworthy revival of the ‘tough guy’ image thanks to American action stars like Chuck Norris and Sylvester Stallone. As a result of films like Rambo and Missing in Action, men started growing their hair out, getting tattoos, and taking their shirts off far more than was appropriate. You then saw many family portraits like this one, where these brothers have assumed an extremely intimidating composition. Back off, dude.
The Ultimate Dudes
Demon Child
Were you the odd one out growing up? Did you struggle to relate to other people? Did you find that people were scared of you? If so, it might have been because you refused to take off your Halloween mask long past a big night of trick or treating. It seems like this kid became emotionally and literally attached to his scary mask, and his parents could not convince him to take it off, not even for an otherwise wholesome family portrait.
Demon Child
Puppy Perfection
‘Dog people’ are known for being far too passionate about their pooches, treating them far better than other people treat their actual children. In this family portrait, one can clearly see how seriously these ‘fur parents’ take their roles. Getting a shirt saying ‘World’s Best Dad’ with a picture of your doggy is some serious commitment. As for the puppy itself, it looks rather afraid, don’t you think? Don’t worry, little guy, it will all be over soon…
Puppy Perfection
The Dentist’s Kids
No, this isn’t a promotional poster for the new Saw films. These kids are getting their whole jaw rearranged with the horrifying orthodontic headset. If you had to go through this grizzly-looking process as a child, then you might be feeling for these kids, rather than cringing. Still, they do look happy, even if it looks like their headsets are stretching their smiles! Well, at least they will have perfect teeth and a correctly aligned jaw by the end of it all.
The Dentists Kids
Sunglasses Lovers
It seems that wearing sunglasses to family portraits was a hopefully short-lived trend of the 80s. There were many peculiar things that people loved doing during this edgy period, but appearing like the family of a secret service member must be the weirdest. This image just screams 80s kitsch. The clothes, hairstyles, and, of course, the accessories. If you felt nostalgic looking at this picture, then you might have followed this trend once! Thank goodness we live in 2021.
Sunglasses Lovers
Put Me Down!
We get it. You love your dog. But for the love of pets, put Fido down! He looks very uncomfortable and unhappy. We are not sure why this eager owner decided to hold his pooch upside-down, like The Undertaker about to Tombstone Piledriver someone. As sorry as we feel for the dog, we cannot help but laugh at his pitiful expression. His tail is tucked between his legs in fear! That’s it, I’m calling the police.
Put Me Down
Rather Be Asleep
Family portraits can be a real drag. If you are not in the mood to preserve your precious family moments in time, then this process can be incredibly tiring. That being said, it’s usually kids that begin performing or falling asleep, and not moms! We love how this lady could no longer hold the yawns back. To be fair, this does look like a drab affair and setting. Maybe this family should have spiced things up like the other ones on this list.
Rather Be Asleep
Boxing Santa
It seems that Santa got a little bit confused with the meaning of boxing. Rather than wrapping up presents, he got into a nasty fight with someone. We are not sure which company hired this grizzly-looking chap, but surely there were sweeter-looking old men to do the job? Arriving at any job with a black eye is cause for concern, but when your job is to entertain children, you might want to take the day off, instead.
Boxing Santa
Rollercoaster Ride
Is this kid having his family portrait taken or is he on a roller-coaster? We have no idea what frightened him so intensely, but it must have been seriously startling to elicit such a wild expression. We are glad that he found some excitement in an otherwise boring situation. This picture seems quite old, and the kid must be an adult by now. We hope that he looks back on this picture fondly and never changed.
Rollercoaster Ride
Balls To The Balls
Playing with your kids is generally a safe and pleasant affair. Sometimes, however, they find a way to really hit us where it hurts. Like this poor dad, who was mildly kicking a ball around with his daughter when disaster struck. Looks like mom captured the moment of impact perfectly, just as the ball is smashing his delicates. We love that O-face of agony. Let’s hope that this girl got a yellow card for that foul play.
Balls To The Balls
Domination
Sibling rivalry is a sad but inevitable part of family life. And there is zero-tolerance when it comes to Christmas day, especially when your sibling gets a present that you desperately wanted. This merciless girl didn’t pull her punches when her baby sister was gifted with some 101 Dalmatians-themed toys. When it comes to toys, kids will go to any length to get them, even if it means wrestling a baby. Let’s hope this bullying didn’t become a trend!
Domination
Protesting Elf
Santa’s elves generally work tirelessly to build the children of the world’s toys. They get little to no pay, being satisfied with the smiles and laughter that they bring to kids. Sometimes, however, an elf needs more than just compassion and candy. This little elf decided that a protest was in order, and began bawling intensely to the camera. Well, she was actually quoting an emotive section of The Communist Manifesto that brought her to tears.
Protesting Elf
Farmers’ Family Portrait
This image might look like something out of Children of the Corn, but it is perfectly harmless. We hope. Pictured is a gentleman with a phenomenal beard riding a mount of sorts made from hay. His wife, to the right of him, looks on in astonished reverence, while his sister just plays it cool. Why pay a photographer and a studio to do your family portraits, when you can make your own bizarre and representative ones?
Farmers Family Portrait
Natural Portraits
What looks like a poor man’s Colin Firth and his family decided to take their family portrait theme to something best reserved for the calendars found in mechanic shops. We do not understand why they thought that this would be a cute or ‘natural’ family portrait. It makes the viewer want to call Child Protection Services, and we hope that these folks consider keeping their shirts on for the next family photoshoot. We feel for the photographer.
Natural Portraits
The Next Dimension
We’ve seen some strange family portraits on this list, but we think that this one tops it. What on Earth is going on here? An otherwise normal family portrait is given a surreal spin when the enormous faces of said family members start peaking in. Are they supposed to be optimistically staring into the future? The way the kid is staring into our souls on the far right is very unsettling. I think it’s time we moved on…
The Next Dimension
Happy Family
Try as he might, the photographer could not get this glum family to cheer up. He told jokes, made a fool of himself, and even promised them ice cream. Nothing worked. The depressed family simply scowled at him. Remember to cancel your studio booking, dear families, if you all get into an argument minutes before. We cannot help but feel like the dad was the cause of this miserable scene, given his slightly guilty expression. How are you going to get out of this one, pop?
Happy Family
Stay Away!
The elderly have a perhaps unfair stereotype of being cranky. In this old woman’s case (extreme right), she seems to be suffering from a severe case of antisocial grumpiness. Things got so bad on this formerly pleasant outdoor shoot that granny refused to sit with everyone. It is amazing when those that are supposed to be the most mature and wise among us behave like sulky children. Let’s hope grandma’s stormy mood lightened up soon enough for a sunny family portrait.
Stay Away
Skyscraper Shenanigans
The fear of heights is a very real thing. Personally, I prefer solid ground, thank you very much, and so do these little girls! When their parents decided that going to the top floor of a high-rise building was the perfect family photo opportunity, things backfired pretty quickly. These twins aren’t having any of it, and are screaming in terror! The one girl can’t let go of her mom’s leg she’s so scared. Someone call an elevator, ASAP.
Skyscraper Shenanigans
Tigger Terror
Disney World is the ultimate paradise for children and adults alike. Beyond the phenomenal rides, incredible restaurants, and beautiful parks, one of the big attractions for kids is meeting their favorite Disney characters. But when this family was approached by the energetic Tigger from Winnie the Pooh, one of the daughters hid in fear. She’s ducking under the table like a real tiger just appeared! Let’s hope she managed to finish her pancakes, at least.
Tigger Terror
Leggy Dad
There was a dark time in men’s fashion when wearing the shortest shorts possible was in. We do not know why men felt the need to show off their legs to such an extreme level, and this dad certainly took things too far. He also decided that his booty was worth showing off, too. Well, at least he has a desirable level of confidence. Let’s just hope that his mullet was the only thing hanging out…
Leggy Dad
Nipple Cripple Surprise
The best (or worst) part about kids is just how unpredictable they can be. You never know when they are going to strike, and they can inflict tremendous damage, even when they are babies. This naughty munchkin took advantage of his distracted, shirtless dad to hit him where it hurts with a powerful nipple twist. It doesn’t seem like he’s going to let go any time soon, either. This dad’s patience was fiercely tested – kudos to you, man!
Nipple Cripple Surprise