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 your peers will see and that you'll look back on one day to remember how awkward you looked. Your adult self will be forever grateful to the kid who turned in such a hilarious school picture.
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, funny 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.