50 Hilarious and Infamous School Picture Day Photos

If everyone prepared for picture day at school like the people on this list, then every picture day picture, or mandatory-weird-angled-non-realistic-background-having school photo, would be amazing. What if we could bring stuff like toy swords, horse masks, print t-shirts, wigs, and really whatever we wanted to yearbook picture day? The only people who are going to share them at this point are your parents via picture frames IN YOUR OWN HOUSE! 

So, why not take a ridiculous picture with a dumb shirt that makes you look like an a-hole? Or why not get the yearbook laughs instead of sticking to the unnecessary propriety prescribed to everyone on picture day? This isn’t the 50s, or LinkedIn. These are pictures that your peers will see and that you’ll look back on one day to remember how awkward you looked. Your adult self would be forever grateful to the kid you who turned in one of these kinds of hilarious school pictures.

I always tried to sneak in a crazy face during picture day. Not an insane face that would obviously be unprintable (because, in my day, all the pictures were physical and there was no “digital package”), but one that’d skate by just enough to get the photos I wanted. That way you could trade pictures with a cute girl, and they wouldn’t immediately throw it away during recess. 

From a time where this stuff mattered to parents a lot more, here are the best, school picture day pictures or yearbook photos ever taken of kids who wanted to be a little different, or who unassumingly messed up their picture by doing something accidentally, which is that much more hilarious. 
This Poor Kid

Call the Legal Department






Doubles As Her Business Card






Staring Contest. You and Me, Right Now.






American Eagle. He’s Wearing an American Eagle Shirt.






A Timeless Message






Cheshire Cat Black Dude






Must Be a Very Liberal HS






Revenge of the Band Geeks






Lobbying to Change the School Mascot






And I Thought My Math Teacher Was Ugly






Spreading Truth One Quote at a Time






Overshadowed by the Mullet in the Next Box






Why Have the Authorities Not Been Alerted??






5 Bump Before It Was Cool






But the Kid in Black Face Was Expelled






She Must Have Ditched a Lot of English Classes






Not Even a Text?






Award for Best Troll






Love, Your BFF






Well That Was a Gimme






The Art Department






Clearly He’s the President of the Club






I Must Have Missed That Speech






What Happened to Ben’s Picture?






An Oldie And A Goodie






No, That’s Totally How the Quote Goes






Absolutely Eloquent






So Does She Even Get to Retort?






Megan Is An Accidental Racist






Because This Is Not Hogwarts






He Talk Pretty One Day






The School Said No Burkas






Stone Cold






Before There Were Hipsters






It Was That or Lao Tzu






So That’s Why GPA Doesn’t Matter






Liar.






Still Pissed His Partner Didn’t Show Up






FYC, a White Kid for Fat Albert’s Gang






It Was the Day the Victoria’s Secret Catalog Came Out






Inspired By Nature






Gotta Catch ‘Em All!






They Rejected His Hitler Quote






Because He Gasses the Balls?






Makes Beautiful People Suits in Home Ec






The Hound Went to High School?






That’s What Happens When You Have Photos After Lunch






Would You Send Dynamite?






Please Show Up Well Rested and Sober for Your Photos