16 of Prince William & Prince Harry's Silliest Moments to Date

16 of Prince William & Prince Harry's Silliest Moments to Date

prince william prince harry
Anthony Devlin/PA Images via Getty Images

For those who haven't been paying attention, Prince Harry and Prince William's relationship is not in the best place right now, and both brothers have acknowledged that. It happens, but hopefully won't last long, if it hasn't already been repaired without us catching wind of it (fingers crossed).Throughout the years, the brothers have always been very close -- close enough to have plenty of laughs together -- whether they're just being silly, ribbing each other, or playing a prank on someone else. 

And of course, plenty of those moments have been caught on camera, because, well, these guys spend a lot of the time in public, having their picture taken by throngs of photographers who are ready and more than willing to capture all of the antics. (Hooray for that.) Those moments are very entertaining.   

"Boys will be boys," they say, and that definitely appears to be true in WIlliam and Harry's case. They've played and roughhoused with each other since they were little kids, of course, and it has only increased over the years. Before their relationship hit the skids (hopefully temporarily), they couldn't talk about each other in interviews without including a playful dig or two -- whether it was Harry making a joke about William's lack of hair and dancing skills, or the future king having a go (as Brits say) at Harry's sad love life and red hair. 

But the best moments have always come when the brothers are out together doing a royal visit. They've tousled with each other, raced each other, joked, mock-fought, and pretty much done what siblings do who love each other and are comfortable enough with each other to joke and laugh. In many pictures, they look like they're having a ball together, and ya know what? That's infectious, because we laugh along too. 

Here's hoping that Princess Diana's boys patch things up soon and continue to be close -- and continue to laugh together. Until then, here are 16 times they had silly fun together. 

  • A Good Scare

    princess diana and prince william and prince harry at theme park
    Mathieu Polak/Getty Images

    Both their parents were devoted to them, but Diana had a particular knack for teaching Harry and William to have fun -- and by doing so, bond as brothers -- it seems. She took them to different theme parks, on beach vacations, and similar excursions. Here, the brothers enjoy getting splashed together on a flume-type ride at Alton Towers, an amusement park in England. We're sure they carry those amazing memories with them to this day.

  • Twinkle, Twinkle

    prince william and prince harry as babies at piano
    Tim Graham Photo Library via Getty Images

    What an adorable and fun moment! In 1985, Diana and Charles had a photographer and videographer come over to photograph and record the family, including a preschool age William and toddler Harry. The tiny brothers decided to provide the entertainment by banging out a tune on the family grand piano. William clearly can't resist laughing at his own musical creation, while Harry looks like he's belting out a ballad.  

  • Snow Bunnies

    prince harry and prince william sledding in snow
    Julian Parker/UK Press via Getty Images

    The royals love to go on ski vacations around Europe at least once a year, and William and Harry have been very much part of that tradition all their lives. It definitely looks like they've had plenty of fun. In this picture, it appears they hit the bunny slope with winter equipment no kid could resist (along with, ahem, certain adults): big, bright sleds or saucers. 


  • Who's The Future King Now?!

    prince harry prince william and kate middleton
    Chris Jackson/WPA Pool/Getty Images

    Harry, Kate, and William took time to visit the studio where the Harry Potter movies were filmed in London, and the two bros had a good time casting spells on each other. Hmm. Gotta wonder which one Harry is casting here, cause ya know he made some joke at William's expense. Our guess: an incantation to regrow hair. William's counter-spell? We're thinking one to turn Harry from a ginger to a blond.

  • Take That, Darth Brother!

    prince harry and prince william battling with light sabers
    Adrian Dennis/AFP via Getty Images

    We're definitely sensing a theme here: Harry, taking it to William with whatever weapon is around. In this case, the weapon of choice is a light saber from the Star Wars set in London. (Jealous much?) Guess we shouldn't be surprised. Back in 2016, William seemed to have it all -- a family of his own, a throne in his future -- and Harry had nothing but a string of failed relationship and a military career in the rearview mirror. 

    Hang in there, Harry!

  • Is That Thing Loaded?

    prince harry and prince william with a snake
    Chris Jackson/Getty Images

    That's an African rock python, in case y'all were wondering. No, it's not venemous, but somehow that's not terribly reassuring to William, who is once again being mock-accosted by his little brother -- but he looks like he's enjoying it! Never mind that this snake kills by squeezing its prey to death and can stretch out wide enough to eat an entire antelope. These two will do anything for a laugh.

  • Elementary, My Dear Brother

    prince william and prince harry with magnifying glass
    Arthur Edwards - WPA Pool/Getty Images

    We have no idea what's going on in this picture taken during an event at Buckingham Palace, LOL. Ever the comedian, a prebearded Harry is pointing a magnifying glass at William -- as if he just inspected him and doesn't know quite what to make of what he found. Was it a hairy wart? Lonely hair follicles? A soul dying to be liberated from the weight of looming responsibility? 

    We'll never know.

  • Catch Up, Old Man!

    prince william and prince harry and kate middleton
    Alastair Grant - WPA Pool/Getty Images

    Soon after Kate, William, and Harry set up a mental health initiative together, they held an event at the London Marathon training day. We can see the playful sense of competition between William and Harry, who are clearly going all out to beat each other. (Poor Kate didn't stand a chance.) Harry is just a step ahead, and looking like he's about to fall to the ground laughing. 

    All in good fun!

  • Smell My Finger

    prince wiliam and prince harry
    Max Mumby/Indigo/Getty Images

    We love William's deadpan face in this one. Harry and William's silly moments usually feature born prankster Harry trying to get a rise out of William. Not this time! At the Invictus Games, William gave Harry the finger, and we're still trying to figure out whether he meant to give Harry a fleshy mustache or was telling him to shut up already or making him take a whiff. Whatever it is, it must have been fun for William to be the one doling out the jokes that day.

  • Just a Pair of Not-So-Stiffs

    prince harry and prince william lying side by side in lesotho
    Chris Jackson/Getty Images

    We gotta love that Harry and William are always up for doing fun stuff with people that they meet on official visits and that they look like they're having fun doing it. Here, they're playing a game with children in Lesotho, Africa. Although we have no idea what game it could be, it seems as if William is digging his little brother's mad skills at playing a dead guy. Just another day of cutting up together.

  • Rawr!

    prince harry and prince william and prince seeiso
    Chris Jackson/Getty Images

    Same trip, more antics! William and Harry joined Lesotho's Prince Seeiso in doing a dance while at a children's club. Clearly, the dance involved a lion in some way, because they're all making lion paws and giving their best roar. William is really into it, while Harry looks like he's about to double over in laughter. This photo is so fun that it makes us want to turn back the clock and join in.

  • Inside Joke

    Princess Beatrice and Kate Middleton and prince william and prince harry
    Rota/ Anwar Hussein/Getty Images

    Princess Beatrice and Kate Middleton don't have a clue what these guys are pointing to and laughing about at the Diamond Jubilee Concert near Buckingham Palace. (Must be a brother thang.)  Whatever it was, the brothers saw it at the same time and were totally triggered. Sometimes, being silly together doesn't require anyone else getting the joke and joining in.

  • Really, Dude?

    prince harry and prince william
    Max Mumby/Pool/Indigo/Getty Images

    Harry may love sports and can often be seen screaming at teams and cheering along at his seat, but on this day? He looks like he's listening to the worst, most off-key rendition of a team flight song ever, courtesy of William. The look on his face is priceless, and we're betting his next move is to rub his knuckles on big bro's head and give him a massive noogie -- and then have a good laugh together, of course.

  • Check it out, Pops

    prince william, prince harry, prince charles
    Mark Cuthbert/UK Press via Getty Images

    Hey, why leave dear old dad out of the fun? We're not sure what the boys were showing Prince Charles, but given how famously squeamish and precious he is (the man wears a pinky ring in the year 2020 for crying out loud), he's probably easy prey. Apparently, taking a break from pranking each other, Harry and William teamed up to freak out their dad, and the look on his face makes it clear that it worked. 

    Good one, guys.

  • Wrestlemania

    prince william and prince harry
    Jamie Simpson - WPA Pool/Getty Images

    Harry and William visited Scotland and were part of an indoor soccer match (we didn't even know that was a thing!), but as usual, they seem to be enjoying playfully shoving each other while going for the ball. Clearly, neither one of these guys is the next David Beckham, but they'll take any opportunity to show each other who's boss. Raise a hand if this is basically everyday life now, while we're all stuck at home with family.

  • Cool Story, Bro

    prince harry and prince william as teens
    ROTA/Getty Images

    Harry and William were leaving the royals' annual Christmas Day service at St. Mary Magdalene Church in 2003 when photographers snapped this shot of them cracking up -- and a red-faced Harry looking particularly amused. We're just wondering what was so funny? Did the priest go hilariously off script during his holiday sermon, or did Camilla cut the cheese in the middle of it?


More Slideshows