Wednesday night marked a new low for the Duke of Sussex. American viewers were left flabbergasted after Prince Harry turned up on The Late Show with Stephen Colbert and delivered his most cringeworthy television appearance to date (and there have been a few).
This came on the same day as he made an awkward cameo in his wife’s nauseatingly saccharine Christmas show on Netflix, With Love, Meghan: Holiday Celebration. The appearances have left royal watchers asking: has Prince Harry hit a new low in his quest for success in the US?
While Meghan appears to be thriving in her natural habitat, working on her lifestyle business As Ever, releasing her Netflix shows and even heading back to set for an upcoming Amazon-MGM Studios film alongside Lily Collins and Brie Larson, Harry is flailing.
From failed projects to awkward interviews, experts say Prince Harry ‘is not taken seriously’
60 Minutes
His own Netflix projects have been total flops, with Heart of Invictus gaining some of the lowest viewing figures on the streamer in 2023, while the documentary series he produced last year, Polo, was widely panned.
‘In LA, Harry is not taken seriously – he’s regarded as Meghan’s plus one,’ says LA-based royal expert Kinsey Schofield, host of Kinsey Schofield Unfiltered.
‘It is obvious within the industry that Meghan is the ambitious one, Meghan is the breadwinner and Hollywood fame is her goal. Harry’s lack of work ethic has become infamous in a very short amount of time.’
With the businesses he’s involved in constantly turbulent and his TV and podcast bookings appearing increasingly desperate, we take a look at Harry’s clumsy attempts at finding a purpose since leaving the royals in 2020.
Humiliating appearances on chat shows and podcasts
Prince Harry’s turn on The Late Show with Stephen Colbert had to be the most excruciating of a flurry of toe-curlingly embarrassing TV appearances.
The cringe factor was set to maximum before the show even aired, with the Duke’s appearance trailed by a frankly bizarre clip of Harry and Stephen lip-syncing to a viral Great British Bake Off moment between Alison Hammond and contestant Mark Lutton.
The Duke’s jokes ‘failed to land’ on The Late Show
CBS
In the clip, Harry plays Alison, who asks Mark what he’d want her to do if he were ‘king for the day’. Harry fully hams it up, mouthing along to when Alison mishears Mark’s response of ‘bake for me’ and thinks he’d want her to ‘beg’.
Meghan shared the awkward skit on her Instagram account ahead of the show, where Harry then went on to make a series of painful jokes that failed to land.
In one, he mocked Donald Trump by claiming America had ‘elected a king’ – showing there’s still no love lost between the Prince and the controversial US president – and said that America was ‘obsessed with royalty’.
He also pretended he’d ended up on the show after getting lost while searching for an audition to play a prince in a Hallmark Christmas movie.
There was no traditional interview and viewers were left cringing at Harry’s lame jokes, leading PR expert Mark Borkowski to brand the appearance an ‘embarrassment’.
‘What we’re seeing is the classic identity vacuum of a man who walked out of the royal machine without building a new one to stand in,’ Borkowski said.
‘Every skit, every podcast cameo, every crowd-pleasing wisecrack is an attempt to reverse-engineer a persona the public never actually asked for.’
That same day, Harry also made an awkward cameo in Meghan’s critically panned Christmas special on Netflix. In it, he was seen tucking into a bowl of gumbo inspired by Meghan’s mother, Doria Ragland’s, recipe and dissing what he called her ‘anti-salad’, made using all of his least favourite ingredients.
Prince Harry in Meghan Markle’s Netflix Christmas special
Netflix
The appearance marked Harry’s first ever speaking part on one of her shows, and while he’s made small cameos on earlier seasons of With Love, Meghan, critics have noted he always seems incredibly uncomfortable beside his wife’s sunny American friends.
Attempts to ingratiate himself with the locals haven’t come over any better, if Harry’s October appearance on comedian Hasan Minhaj’s podcast Doesn’t Know is anything to go by.
While there he was awkwardly forced to put on his best American accent to say phrases including ‘I ordered breadsticks with ranch dressing at Applebee’s’ and ‘Hey, do you like my Cybertruck?’ Hardly the sort of thing you’d expect from the man who’s fifth in line to the British throne.
The Prince was also left completely flummoxed when Minhaj asked him what he thought of the ongoing feud between Taylor Swift and Charli XCX, with Harry looking baffled and desperate for the conversation to be over.
Things aren’t faring much better at the Duke’s paid-for positions, where staffing issues are a major problem. At Travalyst, the eco-friendly travel company Harry founded in 2019, this month sees the departure of the firm’s chief executive Sally Davey, who handed in her notice in September after five years in the role.
Described as a ‘huge blow’ to the company, Davey follows in the footsteps of Travalyst’s first chairman, India Gary-Martin, who left her position after less than two years on the job in January.
Harry and Meghan’s charitable foundation Archewell has always been described as a ‘revolving door’ when it comes to staff and it would seem Travalyst is no different.
Archewell is known for having a high turnover of staff
AP
Davey has now become the 20th senior staffer working for Harry and Meghan to hand in their resignation over the past five years.
Harry established Travalyst in a bid to make travel more environmentally friendly, but was quickly mired in scandal after it was revealed he and Meghan had been using gas-guzzling private jets. The year the business launched, the couple reportedly made four journeys by private jets in the space of 11 days. Harry’s response? ‘No one is perfect.’
Meanwhile, last year the $5 billion mental health startup where Harry acts as chief impact officer, BetterUp, was branded a ‘toxic train wreck’ and ‘psychologically unsafe’ by former employees.
Harry was appointed to the role in March 2021 and has been a vocal campaigner for the Silicon Valley life coaching startup ever since. However, staff members have taken to recruiting website Glassdoor to air their frustrations with the company, with one worker declaring BetterUp’s ‘elitist club of leaders’ had ‘no moral compass’ and saying they ‘lack self-awareness’. It all sounds worryingly similar to reports of disgruntled staff at
Archewell; indeed, it’s said that some of Harry and Meghan’s former employees describe themselves as part of the ‘Sussex Survivors Club’.
Perhaps Harry’s most headline-grabbing career move since quitting Britain for the US was the release of his explosive memoir, Spare, in January 2023.
The original hardback version clocked in at 416 pages, while last year’s paperback release featured a whopping 528 pages. That’s a lot of dirty laundry to air.
The Duke of Sussex went into great detail about his family relationships in his memoir
Getty/ Andrew Parsons / Kensington Palace
The no-holds-barred account revealed shocking details about his private life and his family – from how he lost his virginity to the revelation that he and William once had a physical fight over Meghan which ended up with Harry landing on a dog bowl.
While the book was a commercial success, selling over six million copies worldwide, royal insiders were appalled by the bombshell secrets it revealed and it’s said to have caused an irreparable rift between Harry and his immediate family, most notably his brother and father.
Even Harry himself admitted the damage the book had caused in a recent interview with the BBC: ‘Of course, some members of my family will never forgive me for writing a book,’ he said. ‘Of course, they will never forgive lots of things.’
Branded whiny and self-obsessed by many, it certainly did nothing to help Harry’s public image.
As for his royal cache in his newly adopted home, that too seems to be dwindling fast. ‘People cannot stand the hypocrisy – you cannot call the institution toxic while still dining out on it,’ says Schofield.
‘Either build your own lane or stop biting the hand that feeds you. Harry knows his only real value is his proximity to the British royal family. It haunts him.’
As Harry continues to spiral into irrelevance, his angry press interviews have become some of the hardest things to watch.
The Duke of Sussex gave a tense BBC interview following the decision on his security provision
BBC
Since leaving the UK in 2020 there have almost been too many to list, but the most recent one was with the BBC this May, after Harry lost his years-long battle over his security.
Instead of slinking off quietly to lick his wounds, Harry gave an extraordinary interview in which he described the decision as a ‘good old-fashioned establishment stitch-up’.
One critic branded the interview ‘awful, slick with entitlement and ignoring the harm done by his own hostility’, while others were appalled by his woe-is-me victim mentality. But I think we can all agree on one thing: such interviews are the sign of a man who is deeply unhappy with how his life is currently turning out.
‘The optics are bleak,’ says Schofield. ‘Based on Harry’s Colbert appearance, I think he is lashing out. We saw during the Oprah interview exactly what he is willing to do when he is desperate for attention from his family, who I know are not communicating with him right now. He is absolutely lost.’
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