21+ Epic Family Photos You’ve Got to See!

At their best, family photos immortalize the happiest moments in life with your loved ones. At their worst, these portraits can become cringeworthy disasters filled with misbehaving kids, inappropriate tee-shirts, and the occasional photobombing the shot.
Every family has at least one photo that they want to keep hidden away in the bottom of a shoebox in their closet. The good news is, fifty brave people decided to share their failed attempt at nice family photos, making the world a funnier place. Keep an eye out for the final image. You might just recognize yourself, but probably not for the reasons you’re thinking!

1. Good practice for when he starts driving.

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This kid may be smiling sweetly, but deep down, he may be feeling something else. Take a close look at the picture and see how he really feels about being forced into doing yet another portrait session.

2. The do-over.

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In the older photo disaster, the family did everything wrong. It took them over 20 years to find the courage to try again.

3. Slipped it past the school censors.

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This fabric happened to be on sale and this poor girl’s nearsighted grandma didn’t get a close look at the print. While the kissing couples aren’t that bad, we have to wonder why there are video cameras pointed at them.

4.  Nobody should be this happy to find Rudolph…

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One year, Grandma got run over by a reindeer. Next year, she got payback.

5.  Incoming: the newest cool kids at school.

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We’re not sure who we feel most sorry for. The kid with the eyepatch? The kid who wet himself? The kid who’s about to?

 6.  Be careful what you wish for.

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The kids wanted a Super Mario Bros. theme, but the studio was out of overalls and plungers. At least they had a box of week-old button mushrooms lying around for a prop.

7.  It’s like Duck, Duck, Duck, Goose…

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Except it’s bowl cut, bowl cut, bowl cut, rebel! At least the girl on the left doesn’t cringe at this picture.

8.  Four kids, one shovel, no mercy.

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Send your kids to shovel the driveway in their jammies? Prepare for payback, after all, they do have a shovel handy…

9.  The Grandparents asked for some nice family photos …

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After they got sent this revealing gem, they stopped asking. Unfortunately, this was the start of a family tradition.

10. You don’t have to be Sherlock to crack this case…

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Who could have smeared paint on the antique fireplace? Just follow the trail of clues; they lead straight to the culprit.

11. Three questions:

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First, where was this poor kid’s parents? Second, why do school photos seem to attract inappropriate shirts?  Third, how do you even get a Playboy bunny t-shirt in a kindergartener’s size?

12. Matching couple portraits can go wrong so easily.

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Here’s to true love: they’re both willing to wear acid-washed mom jeans and painfully bad appliqued sweaters.  Thank goodness the 80s are over, but we’ll always have the memories (and the photographic evidence).

13. Waiting for the prom date.

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Nothing cools down raging teenage hormones faster than Dad, shirtless, in Daisy Dukes. If we were her date, we’d tell the limo driver to keep going.

14. Worst school photo fail ever?

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The full phrase on the shirt: “Rub it easy, make it hard.”  ‘Nuff said.

15. Baby’s first Christmas fail.

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At one year old, this kid knew this photo would become an Epic Fail. What’s Mom and Dad’s excuse? Too much eggnog?

16. Mom wasn’t in on the joke.

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Three out of four people thought it would be hilarious if the girl in the back looked like she’d forgotten her top. Unfortunately, the photographer caught the exact moment Mom realized the awful truth.

17. Groovy, baby.

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You know why the Seventies were so awesome? Because three generations could rock hair like this. Gotta love those leisure suits, too.

18. Daryl Dixon: the early years.

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He and the missus have been ready for the zombie apocalypse since the 80s. Now all he needs is a motorcycle and a band of scrappy survivors.

19. Celebrities going the extra mile.

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The husband may be kicking himself for missing the family photo shoot, but his family doesn’t mind. His wife finally gets to live out her 80s fantasy and have smooth operator Eddie Murphy by her side. The kids look thrilled too; this cardboard stand-in of Eddie Murphy gives them a lot fewer chores.

20. No shirt, no shoes, no service.

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Come back to the dinner table, son, when you’re ready to eat like a civilized human being.

21. Remember, always check your photos before uploading to Facebook.

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Make Ma and Pa feel like they’re part of your field trip to the Grand Canyon by sharing pictures! It’s the perfect plan. Wait, why are they calling rescue services?

22. It’s like you have x-ray goggles!

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Who needs to pay for an expensive ultrasound when your husband is a ‘talented’ artist.

23. Daydreams can be nightmares too.

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The photographer wanted the photo to look like a man thinking fondly of his family. However, the man’s alarmed look and Mom’s crazy hair are straight out of a horror movie.

24. Wait for just the right moment.

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At least it was the index finger this time.

25. Ever notice how many poorly thought-out wedding photos there are?

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The bear’s too small to eat the bride and groom, but that didn’t stop him from trying. And helping himself to the cake.

26. Who can make the crazier face?

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People talk about guard donkeys on farms. This kid can pull a mug that would scare off any trespasser.

27. The snake is the least of his problems.

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Ever wonder what Walker, Texas Ranger, would look like if he formed his own 80s Hair band?

28. Are you ready to write a Plenty of Fish success story?

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Let’s face it, some dating sites are better than others.  The good news, ladies, is that this fine gentleman in his custom-knit sweater is available!

29. My, how fashions change…

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This style was allegedly all the rage in the 50s, though we haven’t seen a photo like this before. We’re sure this woman (and her family) will never forget the distinctive underoos of decades past.

30. Just shoot me.

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If life was an episode of the classic cartoon Loony Tunes, Dad’s thought bubble would appear right next to his head.  Look closely and you’ll see how much Dad’s enjoying this holiday season.

31. You can lead kids to the camera but you can’t make them behave.

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Weirdly enough, it isn’t the scowling little lady in the bottom left who has a secret message for the holidays.

32. When you’re too cheap for a toy horse.

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What do you do when your kids want to be a prince and princess, but you’re on a budget?  Make your own costumes and hope the photos don’t haunt everyone for years to come.

33. Three steps to solid parenting.

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Step one: steal police-issue caution tape. Step two: use it to reserve a whole playground for your kids. Step three: ready that camera.

34. Bachelor party invite? No.

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This awesome family photo was intended as a 25th anniversary present to these boys’ parents. Joke’s on them: the folks keep this displayed on the mantel.

35. Photo studio revenge.

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If this girl had her hand in the picture, she’d send a message to her parents: thanks for the bowl cut.

36. Weddings can break the bank.

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This thrifty young couple didn’t bother renting a pair of doves.  They had all they needed in their freezer.

37. Bringing the 80s back with sass.

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Who didn’t want to be a superhero when they were children? These kids grabbed some glitter, purple tie-dye, and spandex and were good to go. Thanks, Mom and Dad, for telling us we looked great.

38. Sports Illustrated is going in a new direction.

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What could be more glamorous than a photoshoot on a sunset beach? This.

39. Somebody didn’t childproof their artwork.

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Why is this sweet-looking, normally dressed kid in this gallery? Take a closer look at the walls. Seriously, Grandpa, what were you thinking?

40. As tough as week-old gingerbread.

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You can bribe a kid with a cupcake, but you can’t make her cooperate with the photographer.

41. The latest Mommy and Me yoga craze.

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Mommy and Daddy juggle the kids. Fun and fitness on the beach!

42. Happy Halloween, kids.

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Your dad found a job as a billboard. How else can he pay for your sweet lifestyle as princesses?

43. Why’s she smiling?

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Grandma’s always thrilled when her family drops by, through the garage, for a visit.

44. Live dangerously.  No regrets.

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We sure hope this is Photoshopped. They had Photoshop back then, right?

45. Is this photobombing or a full moon rising?

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For this wholesome family, one trip to San Francisco will live on in infamy.

46. Tropical thunder.

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Grandma got lei’d in Hawaii. Think she’s miserable? Think again; this is her ‘thrilled’ face.

47. Runner-up for People Magazine’s Sexiest Man Alive: 1972

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This might be the greatest photo fail we’ve ever seen! We are wondering if all of their family photos look like this.

48. The circle of life.

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You’re born, go to school, work, and drop dead in the driveway.  All in one photo.

49. They dropped a grand in hairspray alone.

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Priscilla Presley herself didn’t have the guts for these beehives.  Or the sweet homemade suits.

50. Ever wish you could go back in time…

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And slip on a disguise before those unforgettable family photos were taken? For once, these rock star look-a-likes got it right.

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