It’s a fall evening in 2014 in London, England, and comedian Jack Whitehall takes to the theater stage at The Palladium. The massive audience sits expectant, eager for a few minutes of wit and banter from the funnyman and he doesn’t disappoint. But one person in the audience does not seem to be enjoying his patter: Prince William.
The crowd roars with laughter as Whitehall gently flirts with William’s wife, Kate Middleton. But it seems that the prince might not be finding Whitehall’s cheeky jibes quite as amusing as the rest of the audience. After the show, the royal corners the saucy comedian with the intention of having a private word with him.
The comedian was doing his turn at the Royal Variety Performance. Every year since 1912 a show has been put on for charity, and over the years it’s become something of an institution. More than 150 million people across the world enjoy the show and so do members of the British royal family, members of which attend each year.
In 2014 it was the turn of the Duke and Duchess of Cambridge, the latter showing off her baby bump, as she was expecting Princess Charlotte at the time. The show was destined to be a massive hit, enlivened by comic Michael McIntyre, who hosted, and a glittering parade of British stars, not least of them ginger troubadour Ed Sheeran.
Also on the bill was Jack Whitehall. He was a good catch for the show: an all-rounder, he’s had a career as actor, writer, presenter and, above all, comedian. He first trod a stage on the Edinburgh Fringe back in 2007 where he carried off awards with his sparkling humor. And those weren’t his last accolades; indeed, his successful career to date has been jam-packed with gongs.
Although Whitehall’s career kicked off on stage, his face is also often seen on TV and on the bigger screen too. You might well have seen him on Netflix, where his show Travels With My Father, in which he appeared alongside dad Michael, has proved popular. Or you might have caught him in Disney films, which he’s graced a couple of times.
Be that as it may, standup is where the comedian’s heart is. At the time of writing, Whitehall is selling out venues for a huge tour – Jack Whitehall: Stood Up – which will no doubt repeat the success of national shows in 2014 and 2017. He’s also hosted many awards and variety evenings, including the Royal Variety Performance itself.
As well as a funny guy, Whitehall has a bit of a reputation as a ladies’ man. His dad Michael chided him for flirting in a TV episode of their BBC2 and Three chat vehicle Backchat. Not that he restricted himself to the ladies! No, Whitehall will also share cheeky innuendo with his male guests too.
Even in the world of social media, Whitehall likes to get personal with beautiful women. In 2019 he caught the eye of socialite Paris Hilton, who was quick to let him know how attracted she was to him on Instagram after a bout of flirty chatter. She isn’t by any means the only celebrity lovely to have her head turned by Whitehall’s smooth good looks.
Among those Whitehall has squired is long-time lady friend Gemma Chan. The talented star of Crazy Rich Asians and U.K. TV hit Humans formed a celebrity couple with Whitehall in 2011 when they hooked up after starring in TV show Fresh Meat. Sadly, the relationship ran aground on the rocks of two very busy careers.
The funnyman talked about breaking up from Chan on stage in 2018. He told the audience, “I’ve had a lot of changes in my life recently. I’m single now. I was in a relationship, it broke down, it was not gonna work, it was a long-distance relationship, not geographically, just in terms of our expectations.” And it wasn’t just busy lives that got in the way, he explained, saying, “She wanted kids now whereas I wanted to escape. I’m not good with kids.”
Earlier that year, Whitehall had set the gossip pages alight after being seen at an awards bash kissing singer Dua Lipa. A source told U.K. tabloid the Daily Express, “There was no denying the chemistry between them. Jack was grinning from ear to ear as they chatted together and Dua clearly loved the attention.” And Lipa was just one of a set of celebrity girlfriends who the comic dated.
In 2020 the funnyman found something a little more lasting as he coupled up with Roxy Horner, a model from the English county of Essex. A source shared details with U.K. redtop The Sun, claiming, “It’s all very new but they’re in their own little bubble and things are perfect at the moment.” The insider explained why they felt the romance was special, adding, “Both have had their share of heartbreak and struggled a bit to find love. It’s time they had some luck.”
Whitehall met the British beauty on his travels in Australia, and it wasn’t long before the pair were making a home together. Horner moved in with Whitehall in his residence in London. Although the comedian accepted that it had all happened very quickly, he seemed deeply in love with his belle.
So with his track record, perhaps it’s not surprising that Kate Middleton had caught the eye of Whitehall. After all, she had attracted the gaze of a prince of the realm while a student of art history at the University of St. Andrew’s, which the prince also attended.
Still a teenager, Kate had taken part in a fashion show at the university. And in attendance was Prince William, who was knocked sideways by the vision of Kate in a sheer dress. He’s reported to have told a buddy, “She’s hot!” It seems that it was the first time that he’d noticed, since they’d had a friendship before the fashion parade.
Romance did not take long to blossom after the show, and the two were an item by the time they graduated university in 2005. William set off for military school, and Kate took a job at a clothing retailer. Being apart – him in Sandhurst, her in London – didn’t prevent them from enjoying time together, sharing a love of clubbing when he had leave in the capital.
But it wasn’t all smooth sailing. No, having very different courses in life coupled with the glare of the British media led them to go back to the single life in 2007. Not for long though! The year wasn’t even out before they were a couple once more, and talk of an addition to the royal family started to grow.
In 2010 William popped the question to Kate, and of course she said yes. A year later, she finally became the newest royal when the two said their vows. You may remember the kiss the newlyweds shared on the balcony of Buckingham Palace – certainly the crowds that flocked to see it won’t have forgotten it.
One reason that the couple had attracted the devotion of the public was being so down to earth. Once wed, they didn’t immediately start palace-shopping. No, they stayed in their cottage home on the remote Welsh island of Anglesey. And surprisingly for a prince and his bride, the pair didn’t hire servants, telling U.K. newspaper The Daily Telegraph that they “would ruin the intimacy of their relationship.”
It wasn’t all cozying up in rural Wales, though. The pair had royal duties to perform and red carpets to grace. And they did it in fine style, with Kate catching the eye in a succession of glamorous outfits. Meanwhile, they enjoyed touring as royals too, visiting the far-flung Pacific island group of Tuvalu as well as the less-exotic climes of Canada.
The whirl of events and tours had to slow a little as 2013 dawned because Kate was pregnant and in the grip of fierce morning sickness. It proved worth it, though, because she would welcome son Prince George in July of that year. The birth was, for Kate, a “life-changing moment.”
It wasn’t long before the Cambridge family had grown further with the addition of Princess Charlotte in 2015. Motherhood clearly agreed with Kate, since she didn’t stop there, having a third child, Prince Louis, in 2018. In 2020 the family of five made their first public appearance as a group.
Throughout their relationship, the Duke and Duchess have been in the spotlight. But we think it’s fair to say that they have lived up to the promise that they had made when first married. As a source said to BBC America in that year, “They want to do their duty and make sure they are a real asset to the country, but they are private individuals who want to get on with their lives.”
So as part of their royal duties, the Duke and Duchess were attending the Royal Variety Performance on November 13, 2014. And out trotted Jack Whitehall. He told the crowd, “I’m very excited to be here. I’m especially excited to be here performing in front of the Duchess of Cambridge.” But why “especially excited?”
Well, it turns out that the two have a connection that you might not expect. Yes, Whitehall and Kate happen to have gone to the same private school, the elite boarding establishment of Marlborough College. But, because Kate is by some years Whitehall’s senior, they didn’t exactly hang out together.
Whitehall told the performance audience, “This is genuinely true, this is so exciting. We were actually at school together. This is true. We went to the same school. I was a bit younger than you, but this is the first time I’ve seen you since school, so hello.” And it seemed that Kate was pretty pleased to find this out because she had a giggle and saluted Whitehall with a wave.
Yet Kate might have wished that she hadn’t encouraged him when she heard what Whitehall said next. He shared, “I don’t know whether it’s appropriate given the circumstances, but you were probably my first ever crush.” Prince William clearly didn’t think that it was appropriate, glaring at Whitehall, who said, “Your Highness is giving me a sharp look.”
And the prince did not let it lie either. After the show, he approached Whitehall to let him know what he thought about the flirting. As Whitehall told TV chat show host Jonathan Ross in 2020, “William came over and he was very funny, he was very nice but very passive-aggressive and said, ‘Oh, so you were flirting with my missus? Oh no that was very funny!’”
It’s probably not a great idea to upset a prince of the British realm, although perhaps the consequences aren’t quite as gruesome as Whitehall suggested to Ross. The funnyman told the chat legend, “That’s him going, ‘I could have you beheaded.’” Luckily for the comedian, the prince was not quite that vengeful!
Not that Whitehall would have ever had a hope of dating Kate. The comedian explained to Ross that young love was in this instance doomed, “She was a lot older than me. She was in sixth form – it was never going to happen, I was in a head brace!” And in any case, who can compete with the romance of being swept off your feet by a prince?
Another prince, Harry this time, had a funny encounter with Whitehall at the very next year’s Royal Variety Performance. Before the show, Harry had shared that the funnyman had caused some anxiety – after all, Whitehall is renowned for his sharp tongue – but he needn’t have worried. The ribbing that he received from the comic was friendly.
The comedian softened the prince up with some praise for his service in the military and work for charity. But then he made the audience laugh with a reference to Harry’s partying, saying, “Yes you’ve served your country with distinction in the British Army. But more importantly than any of that…You’re the kind of guy on a night out who doesn’t see a shopping [cart], but a ride home.”
The theme of Harry on a night out proved fertile ground for Whitehall, as he then described what would happen if someone was to have one too many and pass out around the prince. He laughed, “Stand back, I’ve got this. You get a Sharpie. You take out a camera phone. You hand me that razor. Those eyebrows are coming with me. Yes, ladies and gentleman, he may only be a prince. But when it comes to banter, all hail the king.”
Whitehall had lived up to his billing, which he’d boosted a little beforehand, saying, “It’s a tremendous honor to be hosting the Royal Variety Performance. Having been lucky enough to perform for Prince Charles and Prince William in previous years, I look forward to the opportunity of sailing a little too close to the wind in the presence of Prince Harry this time round.”
Indeed, run-ins with royals are just part of life for the award-winning funster, as he told The Jonathan Ross Show in 2019. Apparently, Whitehall had received an invite at some point to perform at Prince Charles’s Christmas do. Each year, the heir to the British throne throws a bash for his staff and puts on entertainment.
Whitehall found it quite a peculiar event, with more than a flavor of the royal audience. He shared with Ross, “It’s the weirdest gig ever. I walk out, first thing that’s weird is that they’re sat in the front row, Charles and Camilla, in thrones.” And having walked out, Whitehall’s problems began.
Frozen in front of this strange audience, the funnyman reached for a standby, but as he told Ross, it didn’t work. He said, “Also, don’t sit in the front row because that’s your get-out-of-jail-free card as a comic, [you pick on the front row], you ask them what they do for a living… I can’t ask Prince Charles what he does for a living!”
Things soon went downhill for the comic. And he told Ross all about it, saying, “[It was a] small room, maybe 40 people, all of my material was terrible. I absolutely died!” And what made it particularly painful was the reception that the audience gave him. Whitehall added, “Nobody was applauding. It was the worst review I’ve ever got.”
That wasn’t all! As Whitehall slouched away from the performance area, he saw Charles turn to Camilla to give his verdict. The prince, Whitehall reported, muttered to his spouse, “I think next year we’ll try a magician.” In the end, the comedian concluded, “There goes the knighthood!” Well, the comic might yet gain that honor, but he’d better take care if William has by then become king: being knighted involves a sword coming very close to your head!