Prince Harry is no stranger to making headlines - especially since his dramatic exit from life as a working royal in 2020.
But even before the drama around his family dynamics, his sensational memoir, Spare, and his life overseas with Meghan Markle, Harry's hilarious candid moments made for many a memorable moment.
Here, we look back at some of Prince Harry's funniest, silliest and goofiest pictures over the years - from cute moments as a child with mother Diana to funny pictures of Prince Harry and Prince William.
32 candid photos of Prince Harry that show his goofy side
Joking around with Queen Elizabeth
For most people, she was Queen Elizabeth II, the longest-reigning monarch in British history and the very definition of an icon. However, for Harry, she was Gran.
Here, as they both attended Charles and Camilla's wedding blessing service in 2005, Harry proved how he could joke around with the Queen, and she in return seemed to let her guard down and chuckle along.
King Charles III‘s former butler, Grant Harrold, has previously shared more about the "very special relationship" the two shared.
"Sometimes, I wonder if maybe he reminds the Queen a little bit of [her husband] Prince Philip," he said while appearing on a Quest Red royal documentary. "You know, with that wonderful, let’s say, the kind of glint in his eye."
Sticking his tongue out on the balcony of Buckingham Palace
Clearly, Prince Harry has always had that famous cheeky nature that so many people know and love him for.
In this adorable photo, the young Prince doesn't seem to take in the importance of his location, deciding the balcony of Buckingham Palace is just as good a place as any to stick his tongue out at the thousands who came out to see the Trooping the Colour parade in 1988. A classic case of royal children struggling to behave at royal events; they are just like any other children, at the end of the day.
Making President Obama laugh
Prince Harry is well-known for his sense of humour, and it seems he can even crack up figures as important as the President of the United States.
In this delightful candid photo of him and Barack Obama, Harry is animatedly telling a story of some sort, which has the President laughing away.
Harry enjoys a good relationship with the Obamas. In 2016, when the Obamas worked alongside Prince Harry on the Invictus Games in Orlando, they even took part in a jokey social media war between the opposing sides.
During a Good Morning America interview, First Lady Michelle Obama referred to him as, "our Prince Charming."
Marvelling at a moustache
Leave it to Prince Harry to find the time to admire someone's (truly impressive) facial hair during a busy time.
Prince Harry's hilarious photo opportunity came up when he was heading up the 2016 Invictus Games in Orlando, Florida.
The Invictus Games, set up by Harry in 2014, were established to champion the wounded, injured or sick servicemen and is a cause special to the Duke of Sussex.
Trying hard to keep a serious face
Prince Harry took part in his passing-out Sovereign's Parade at Sandhurst Military Academy on April 12, 2006 in Sandhurst, England.
An important rite of passage for those in the military, Prince Harry's cheeky grin stole the show as he tried to keep his composure when Queen Elizabeth passed through the parade to give her approval.
Harry's time with the military would continue, being deployed on active duty to Afghanistan on two occasions.
Letting the paparazzi know how he feels
Prince Harry has let his thoughts on the paparazzi known many times over (spoiler: he's not a fan), but it turns out this attitude might have been there all along.
In 1988, Prince Harry and William were driven to visit their aunt - Sarah Ferguson - and their newly-born cousin, Princess Beatrice.
While leaving the hospital, the young Prince spotted the waiting paps and gave them what became something of a signature expression - a stuck-out tongue.
Sharing champagne in the most unorthodox way
Well, we bet he didn't learn this in the Palace.
Proving that he was just as cheeky and rebellious as any other young man (royal titles be damned), the Duke of Sussex was spotted getting carried away with typical sports hijinks as he drank champagne from a trophy and then spat it out all over a teammate in 2009.
Harry had been taking part in the Veuve Clicquot Manhattan Polo Classic In New York. And we must say, the person receiving a royal champagne shower showed great restraint in what must have been a bizarre moment.
His genuine and infectious excitement
In 2017, Prince Harry made his first official visit to Northern Ireland - and he was clearly delighted to be there.
The warm, friendly Prince looked genuinely thrilled to be meeting crowds at St Anne's Square in Belfast.
His good vibes were infectious, putting everyone around him at ease and ensuring it was nothing but smiles all around.
Doing his best Britney Spears impression
Britney Spears famously performed on stage with a snake wrapped around her, and Princes Harry and William decided they'd give it a go during a 2010 visit to Africa.
The brothers posed with the African rock python during a visit to the Mokolodi Education Centre, and while Prince William had a slight look of fear about him, Harry showed off his playful and fearless nature, seemingly directing the snake's head towards his older brother.
Sticking his tongue out (as an adult, this time)
Ever since he was a child, it seems Prince Harry can't quite help sticking his tongue out - and he relied on his old faithful expression in 2008 when he visited Africa.
Prince Harry was joking with a child during a visit to the Lesotho Child Counselling Unit in Lesotho.
Prince Harry established a charity in the region called Sentebale which worked to provide safe housing for abused children. Sentebale means "forget-me-not" in the native language of the region, and was picked as a memorial to the charity work of his late mother, Princess Diana.
Joking around with Mike Tindall
Without any context, this could seem like quite an alarming photo - and if it was medieval Britain, a Prince making this gesture might have ended with a trip to the gallows.
Luckily, Prince Harry wasn't engaged in some sort of heated exchange or battle, he was simply showing off his classic sense of humour as he joked around with Mike Tindall at friends during a Polo match.
Mike is barely visible, but with his hands in his pockets, the burly rugby player is clearly not taking Harry's wild gesture too seriously.
Classic silly poses for the camera
You might be a Prince and have been thrust into the spotlight since the day you were born but, let's be honest, one of the most relatable things about this photo of Prince Harry is that he still pulls stupid faces when faced with a camera.
The goofy pose was taken as Harry arrived at the start of the Enduro 2008 Motorcycle Rally to benefit UNICEF, the Nelson Mandela Children's Fund and Sentebale, his own charity set up to benefit children in Lesotho.
Making his point
In 2015, Prince Harry visited Cape Town, South Africa where he took part in the Sentebale Royal Salute Polo Cup.
In this amusing photo, you can see that the Prince is trying to make a defiant point as he, Prince Seeiso of Lesotho and Nacho Figueras make it to the end of the game. Did Harry lose? Is he contesting some points? We'll never know, but we're glad we have his cheeky expression caught on camera.
Really loving a Mexican wave
Let's be honest, organised fun and group dances can be embarrassing at the best of times.
So, being forced to take part in a Mexican wave during the 2014 Invictus Games is something which many people might have tried to avoid. Prince Harry gets points for not only taking part in the dance knowing full well the entire stadium would be watching, but his enthusiasm was written all over his face.
Some strange reactions to meeting the public
In 2008, a relatively young Prince Harry took part in an official engagement in Wales.
Now that he's older and wiser, we're used to seeing the Duke of Sussex completely at ease with the crowds. However, this hilarious moment caught him pulling a few odd expressions, betraying his youth and naivety.
Looking terrified while holding a baby is one thing, but was the Prince also playing a game of Rock, Paper, Scissors? We'd love to have been a fly on the wall to understand how that came about!
Making friends
Prince Harry showcased his sweet nature when he simply couldn't resist the cuteness of a dog poking his head out of a car window during a polo match in 2011.
The Duke of Sussex - dressed down in a light, linen shirt and a baseball cap - was smitten with the pooch, crouching down to have a little chat and then scratching him behind the ears.
Pulling funny faces with children
In what's become something of a trademark pose, the young Prince was snapped sticking his tongue out to a group of kids during a royal tour in 2006.
The Duke of Sussex's playful facial expression came as he hung out with a bunch of excited children in Lesotho, a region in southern Africa. His connection to Africa started with the charity work his mum, Princess Diana, started and he went on to found his own foundation in memory of his late mother.
Being a tad dramatic
We love this photo of Prince Harry looking completely goofy and excited as he chats away with a veteran soldier.
Harry's love for the military is well-documented, and he'd go on to serve twice during active duty in Afghanistan, which makes this candid and unguarded conversation so authentic.
The Prince was attending the world premiere of James Bond's Quantum of Solace in 2008, and his very dramatic hand gesture wouldn't be out of place in the actual film.
Throwing a little side eye William's way
As the saying goes, sometimes a picture is worth a thousand words - and we love what can be inferred from this hilarious moment between the royal brothers.
Prince Harry and Prince William had a brother's day out to watch the England v Wales match during the Rugby World Cup 2015 at Twickenham Stadium.
William, cheering on Wales no doubt - seeing as he is the Prince of Wales - was clearly caught up in the action, and Harry's bemused face says it all. Was Harry - formerly the patron of the Rugby Football Union and Rugby Football League - cheering on England? And was that sly little eyebrow raise a smug sign of victory?
Christmas pigtails
While royal fans tend to focus on Kate Middleton's hair secrets or Meghan Markle's iconic messy bun, Prince Harry made his own case for being hair goals in 2012.
The Prince managed to find a way to add some levity to a serious situation. Posing outside the VHR (very high readiness) tent at Camp Bastion, Afghanistan, Harry brought some festive fun by donning a Christmas hat... complete with pigtails and hair ribbons.
We like it, Harry!
Trying something on for size
During the Invictus Games in 2019, Prince Harry was treated to a special gift - a little babygrow for his first-born baby, Prince Archie.
It was a sweet moment for the new father, and he looked genuinely touched by the gesture... but not before joking around with the tiny garment.
Sadly, Harry, they don't make adult clothes quite as comfy as babygrows. Though a onesie is pretty close...
Cracking up with Kate
Prince Harry and his sister-in-law, Kate Middleton, were always a mischievous pair before Harry's exit from life as a working royal in 2020.
It wasn't uncommon for Harry to join his brother and sister-in-law for engagements, and he'd usually end up joking around with Kate. In fact, in many of the candid photos that show Kate's goofy side, Harry is just out of frame cracking a joke.
Here, the pair don't try to hide their genuine belly laughs as they take part in something called 'welly wanging' at a meeting of the Charities Forum at BAFTA in London.
Joking around with Kate Middleton
During Trooping the Colour in 2014, Prince Harry was caught being a goof with Kate Middleton.
Despite being on the balcony of Buckingham Palace in front of thousands, Harry found the time to crack jokes with Kate, seemingly talking into his bracelet re-enacting a secret service agent.
Harry spoke about his bond with Kate in his 2023 memoir, Spare. "She was carefree, sweet [and] kind. She’d done a gap year in Florence, knew about photography, art. And clothes. She loved clothes," the Duke of Sussex wrote.
"Her name was Kate. … I liked seeing Kate laugh. Better yet, I liked making her laugh. And I was quite good at it."
Being a big kid with William
They might be grown up adults. They might be Princes and part of the line of succession to one of the oldest thrones in the world. But, really, William and Harry are just two boys when it comes down to it.
The brothers didn't care about looking proper and regal during a tour of the Star Wars sets at Pinewood studios in 2016, immediately picking up the light sabre replicas and doing battle with one another.
Joking around with Camilla
Since 1748, Trooping the Colour has been the official parade to mark the sovereign's birthday. It's a huge scale operation and attracts crowds of thousands. So you'd think the Royal Family take the day very seriously.
Fortunately, Prince Harry and his comical nature is always on hand to add some light and humour to the pomp and circumstance.
In 2009, he was caught making Prince William and Camilla laugh as they rode in a carriage together.
You're a wizard, Harry
Two Harrys. Both boys thrust into a world beyond their imagination. One of them was a fictional wizard, the other was the very real Prince Harry.
But the worlds collided in 2013 when Harry, Prince William and Kate Middleton attended the opening of the Warner Bros Studio in London.
Trying his hand at seeing if he too was a magical Harry, the Duke of Sussex joked around with a prop wand, aiming his spell directly at his brother.
Tussling with his big brother
Prince William and Prince Harry might have grown up with palaces and privileges many cannot imagine, but they're still siblings. And like any siblings, the two tend to forget all their airs and graces when it comes to competing against one another.
The pair went head-to-head during a five-a-side football match to mark the 20th Commonwealth Games in Scotland in 2014. And while they might not have been dressed for full activity, they didn't hesitate in getting fully invested.
This rivalry has, according to Harry, been there all along. In his memoir, Spare, he referred to William as his "beloved brother and arch-nemesis."
Doing the Usain Bolt pose... with Usain Bolt
Even Prince Harry got caught up in the Usain Bolt fever which swept the world when the world's fastest man became known the world over after his iconic 2008 Olympics appearance.
Usain continued to compete for many years after, and he always whacked out his signature pose, dubbed the Lightning Bolt.
In 2012, Harry pulled the pose as part of the build-up to London's 2012 Olympic Games - and then he would later cheekily get a head-start on the race against Bolt.
Inspecting his brother
Prince Harry decided to go full Inspector Morse on his brother in 2014.
During the launch of the Queen's Young Leaders Programme, Harry picked up a magnifying glass and held it up against his brother.
In classic sibling banter, he pulled expressions of shock and horror - clearly wanting his brother to think he wasn't quite Prince Charming underneath the lens.
Sharing popcorn (and silly faces) with a young friend
Everyone remembers Prince Harry's viral moment with a young fan.
The full video is worth digging out, as Harry sits by Hayley Henson and daughter Emily Henson during the 2017 Invictus Games. As Harry is distracted, the cheeky youngster helps herself to some of Harry's popcorn.
A sweet snack is always going to trump royal etiquette when it comes to a child.
Harry, of course, saw the funny side and ended up trading cute, silly expressions with the young girl.
Not a natural mover...
In 2010, Prince Harry and Prince William returned to Africa for a joint visit to the continent which holds a special place in both of their hearts.
The pair's joint trip saw them visit the likes of Botswana, Lesotho and South Africa.
While there was plenty of highlights from the trip, one hilariously awkward moment for Harry came when he had to showcase his dance moves with William and Prince Seeiso.
Harry wouldn't actually become a father until 2019 - when he welcomed his first child, Prince Archie - but he clearly had some dad dance moves in the bank as early as 2010.
Classic brotherly banter
What better candid moment sums up Prince Harry's relatable and down-to-earth sense of humour than this instance of brotherly mockery?
In 2008, Harry was on a trip around Cardiff when he met with throngs of fans. One of them handed him a copy of HELLO! magazine, which featured his brother on the cover.
Clearly unimpressed, Harry took the magazine and made his (good-natured) dissatisfaction evident.
