A look back at Prince Harry’s most hilarious moments – from THAT Meghan Markle birthday video to bizarre television appearance

Prince Harry isn’t afraid of stepping into the spotlight and showing his more daring and fun side.

The Duke of Sussex often goes to great lengths to entertain others and his most recent trick was appearing to get a tattoo in a hilarious sketch with Jelly Roll.

He also made a bizarre television appearance on Jimmy Fallon‘s Tonightmares back in September where he chaotically made his way through a maze.

Harry’s antics go as far back as his mic drop moment with the Queen in 2016. And the duke showed he can be adventurous with his outfits when he wore a superhero costume for a charity video in 2022.

He made his wife, Meghan, giggle in a video for her 40th birthday and proved he was up for some fun at the WellChild awards in September. 

Read on below as MailOnline looks back at Harry’s hilarious stunts over the years. 

Jelly Roll giving Prince Harry a ‘tattoo’ in a video to promote the 2025 Invictus Games last month

Mic drop moment with the Queen

Harry even managed to get his grandmother, the late Queen Elizabeth, involved with his cheeky antics.

Back in 2016, the prince released a video to promote the Invictus Games which included a clip of him sitting with the Queen. 

In the footage, he shows Her Majesty photographs of the previous year’s Invictus competitors.

Harry receives a text from Michelle Obama, with a video attached. In the playful clip, Barack Obama and his wife ridicule the Prince and state: ‘Hey Prince Harry. Remember when you told us to bring it at the Invictus Games? Be careful what you wish for.’

Three officials can then be seen making a ‘mic drop’ hand signal in the background – seen as a symbol of confidence. 

While Harry looks concerned, the Queen – also known to have a great sense of humour – does not look fazed by the clip and merely states: ‘Oh really? Please.’ 

The clip ends with the Harry turning to the camera cheekily smirking and making his own ‘mic drop’ hand signal.

Harry’s iconic mic drop moment with Queen Elizabeth after watching video from Barack and Michelle Obama in 2016

Juggling prank

His ability to make people laugh shone through when he made an appearance in Meghan Markle’s 40th birthday video back in 2021 when she launched an initiative supporting women going back to work.

The prince featured in the ‘bloopers’ montage towards the end of the footage, when he could be seen stood outside looking in to the room where Meghan sat through a window.

Harry begins to attempt to juggle and throws three balls into the air before dropping them on the ground. 

He tries again but with two balls and flashes a cheeky grin at his wife before disappearing.

Meghan appears surprised and asks, ‘What the?’ before laughing at her husband while Hollywood star Melissa McCarthy, who also featured on the video, giggles.

Harry showing his sense of humour in a video for Meghan Markle’s 40th birthday in 2021

The Prince can be seen juggling balls through a window in the background of the video, making his wife laugh 

Spiderman

Harry showed his humorous but caring side in 2022 when he released a video for bereaved military children at Christmas.

Disguised in a Spiderman costume, he urged the youngsters to have fun in footage for Scotty’s Little Soldiers.

At the end of the video, he pulled off the mask to reveal his face and smiled as he wished the children a Merry Christmas.

Harry dressed up as Spiderman to record a video message for the members of Scotty’s Little Soldiers at their annual Christmas party

WellChild fun

In September, Harry travelled to the UK for the WellChild awards – an initiative he has been a patron of for 16 years.

During the event, he talked with some of the children and shared a playful moment with Noah Nicholson – who had cerebral palsy and chronic lung disease.

The youngster delighted in throwing his soft toys on the floor and watching Harry pick them up. 

When Noah’s mother Tracey Nicholson apologised on behalf of her son, Harry said: ‘Don’t apologise, I love it.’ 

The Duke gets a tattoo

In an effort to promote the Invictus Games in Canada earlier this year, footage was released on X of Harry being ‘inked’ by singer Jelly Roll at a tattoo parlour in New York.

Jelly Roll excitedly greets the prince before sitting down and says, ‘We’re giving you a tattoo about the Invictus Games’. Harry replies: ‘No, I came here to ask you to do the Invictus Games. There’s no tattoo in this. I can’t get a tattoo.’

The pair hilariously strike a deal and begin to discuss the placement of the ink, with the Prince suggesting ‘my lower back or my a***’ and Jelly Roll insists on his neck.

Harry squirms in a chair and shrieks as the American star begins tattooing the Invictus Games’ logo, ‘I am’.

Jelly Roll cheekily adds his own name too, to which a shocked Harry says: ‘You put your name on my neck… are you serious? Oh s***.’ 

Harry receiving a tattoo on his neck from American singer Jelly Roll

Harry’s Halloween hijinks with Jimmy Fallon

During his solo American publicity blitz earlier this year, Harry appeared on television with Jimmy Fallon.

The Prince tried Jimmy Fallon’s Tonightmares, a Halloween experience, at the Rockefeller Centre.

With cameras attached to their chests, the pair made their way through the spooky maze of rooms, falling into fits of raucous laughter, shrieks and screams.

At one point, the animated royal says ‘Jimmy’ before a zombie-like figure jumps out, prompting the Prince to swear in fear, which was bleeped out.

Prince Harry and Jimmy Fallon taking part in an unusual horror maze segment on US television

A camera pointed at the Duke’s face showed his confusion and shock during the maze

The prince screamed and swore as he was jump-scared in a haunted maze

Unexpectedly sharing his popcorn

In an adorably funny moment, Harry found himself sharing his popcorn with a toddler at an Invictus Games volleyball match in 2017.

Emily, the daughter of former Invictus competitor and Paralympian, David Henson, found herself sat next to the prince and took a fancy to his snack.

At one point, cheeky two-year-old Emily put her hand on Harry’s knee and then, seated on her mother Hayley’s lap, proceeded to put her hand in in the Prince’s popcorn.

She managed to sneak several handfuls of the snack while he was engaged talking to a man on his left.

When Harry discovered her hand, he pulled a silly face and deftly pulled his bag away. 

Harry smiling at toddler Emily Henson who had been sneakily eating his popcorn during a volleyball match