Prince Harry’s Comedy Misfire Fuels Claims He’s Chasing Fame The Wrong Way

Prince Harry’s latest late-night appearance was meant to be a festive, light-hearted cameo, but instead it sparked a fresh wave of criticism from viewers and PR experts who say his attempt at humor fell flat.

As awkward jokes piled up and audience reactions shifted from cheers to cringes, many now believe the Duke’s American reinvention has hit an uncomfortable crossroads.

PR Expert Says Prince Harry Is 'Doing It Badly'

Prince Harry’s surprise skit with Stephen Colbert has prompted a sharp assessment from British PR strategist Mark Borkowski, who argues the Duke’s comedic approach and his entire public persona are growing increasingly strained.

Borkowski flatly described the "Late Show" moment as another “embarrassment,” insisting that Harry and Meghan Markle have lost their direction while continuing to “chase celebrity” in the U.S.

He emphasized that Harry's jokes didn’t just miss but also highlighted a deeper issue.

“Harry’s Colbert skit isn’t ‘embarrassing’ because he’s chasing US celebrity, it’s embarrassing because he’s doing it badly,” Borkowski told the Daily Mail.

He added that the Duke’s self-mocking tone no longer resonates with viewers.

“Making fun of your own privilege only works when the audience believes you’ve transcended it. Harry hasn’t. The jokes land like a man reminding you of a punchline that expired three years ago,” the PR expert added.

According to Borkowski, the worn-out humor reveals just how thoroughly the shine has faded.

He said Harry “keeps leaning on the same tired ‘I’m a prince but not that kind of prince’ shtick as if self-deprecation can launder the monarchy off him. It can’t. In America, the novelty wore off the minute Netflix lost interest.”

Inside Prince Harry’s 'Identity Vacuum'

Beyond the awkward punchlines, Borkowski believes the "Late Show" cameo exposes something deeper: a void in Prince Harry’s post-royal identity.

The expert claims Harry is still struggling to align who he wants to be with who the public expects him to be.

“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,” he explained. “Every skit, every podcast cameo, every crowd-pleasing wisecrack is an attempt to reverse-engineer a persona the public never actually asked for.”

In Borkowski’s view, the contradiction is clear: Harry cannot fully reinvent himself while still relying on his heritage to shape the joke.

“You can’t reinvent yourself while still selling tickets to the old you. He wants to be ‘just Harry,’ but every beat of the joke depends on the audience knowing he isn't pushing.”

The PR expert also warned that fame in America is fragile, and Harry’s current strategy isn’t helping him maintain it.

“It’s all got a bit… thirsty. The party circuits. The strategic handshakes… The famous don’t mind being mocked they fear being ignored. Harry’s skating worryingly close to the latter.”

Prince Harry’s Awkward Late-Night Cameo

The controversy began when Harry unexpectedly appeared on "The Late Show With Stephen Colbert" as the host joked about silly holiday-movie titles.

Audience members gasped when Harry appeared behind the host, joking that he was there to audition for a movie role.

As he wandered through the studio, Harry quipped that he was searching for the casting call for “the ‘Gingerbread Christmas Prince saves Christmas in Nebraska.’”

The skit quickly turned political. In one of his riskier jokes, he teased Americans for their fascination with royalty, adding, “Really? I heard you elected a king,” a jab at Donald Trump that immediately drew pantomime boos.

He continued with commentary referencing anti-Trump “No Kings” protests and even touched on CBS’s multimillion-dollar settlement with the former president, calling it a “baseless” lawsuit.

When Colbert pushed back, Harry delivered another punchline, “Maybe that’s why you were canceled,” a joke that earned louder cheers than his earlier attempts.

His historical humor didn’t fare much better. When Colbert called King George III “a jerk,” Harry simply told him, “Let it go.”

A Hallmark Skit That Drifted Into Cringe

Still determined to push through the segment, Prince Harry declared he would “do anything” to land the fake Hallmark role.

He listed his qualifications, “I can ride a horse, fly a helicopter,” before adding even more dramatically, “I can ride a horse in a helicopter!”

Artificial snow fell as Harry played up the idea of being a “handsome prince,” while Colbert insisted the audience “just believe.”

Eventually, the host announced Harry had earned the title of “official Late Show prince of Christmas,” prompting cheers, though viewers later admitted the enthusiasm couldn’t mask the skit’s uncomfortable tone.

This marked Harry’s second visit to "The Late Show," following his high-profile interview in January 2023 to promote his memoir "Spare."

Meghan Markle’s Social Media Tease And Unfortunate Timing

@colbertlateshow I beg your pardon, Stephen? #Colbert #PrinceHarry @The Great British Bake Off ♬ original sound - colbertlateshow

While Prince Harry’s skit was airing, Meghan Markle had already promoted his appearance on Instagram, sharing a lip-sync clip of him parodying a Great British Bake Off meme alongside Colbert.

The timing raised eyebrows, as the moment coincided with the news that her estranged father, Thomas Markle, was in intensive care following emergency surgery in the Philippines.

The contrast between Harry’s comedic antics and the unfolding family crisis only deepened the scrutiny surrounding the couple’s public image.

That scrutiny has only intensified due to Borkowski’s belief that their fame-driven approach is backfiring.

As reactions continue to roll in, one thing is clear: Prince Harry’s attempt at festive humor has become far more serious than he ever intended.