Home / Royal Mail / When Prince Harry was the cheekiest member of the Royal Family: As he prepares to celebrate milestone birthday… 40 times the Duke of Sussex made us all laugh

When Prince Harry was the cheekiest member of the Royal Family: As he prepares to celebrate milestone birthday… 40 times the Duke of Sussex made us all laugh

Since he married Meghan Markle, he’s been striving to be known as a ‘humanitarian’, mental health campaigner and environmental activist. 

Prince Harry, who turns 40 tomorrow, has certainly changed a lot since his younger days.

Gone is the wild young prince of old, and with us now is the more serious, at times embittered, Duke of Sussex.

But there have been plenty of times in the past that Harry – whose cheeky sense of humour used to be regularly on display – has made us all laugh.

Below, we reveal 40 such occasions to mark the Duke of Sussex’s milestone birthday.  

A three-year-old Prince Harry sticking his tongue out at photographers outside of the Portland Hospital in London in 1988, after visiting Sarah Ferguson and his newborn cousin Princess Beatrice

Queen Elizabeth II can't help but grin proudly at her grandson as she inspects soldiers at their passing-out parade at Sandhurst Military Academy in 2006. Prince Harry responds with a small smile himself when she walks by

Queen Elizabeth II can’t help but grin proudly at her grandson as she inspects soldiers at their passing-out parade at Sandhurst Military Academy in 2006. Prince Harry responds with a small smile himself when she walks by 

Prince Harry makes his sister-in-law Kate, then the Duchess of Cambridge, laugh on the Buckingham Palace balcony during Trooping the Colour, 2014

Prince Harry makes his sister-in-law Kate, then the Duchess of Cambridge, laugh on the Buckingham Palace balcony during Trooping the Colour, 2014

Harry jokingly points the head of an African rock python snake towards Prince William, who pulls away hesitantly during their joint trip to South Africa in June, 2010

Harry jokingly points the head of an African rock python snake towards Prince William, who pulls away hesitantly during their joint trip to South Africa in June, 2010

Prince Harry closes his eyes and grins as he tries out a bright orange immersion suit while taking a dip in the Arctic in 2011. He was with the Walking with the Wounded team in Spitsbergen, Norway, as they prepared to walk to the North Pole

Prince Harry closes his eyes and grins as he tries out a bright orange immersion suit while taking a dip in the Arctic in 2011. He was with the Walking with the Wounded team in Spitsbergen, Norway, as they prepared to walk to the North Pole

Prince Harry, aged 13, grinning as he meets the Spice Girls during a visit to South Africa, where they were performing a concert, 1997. He clutches the hands of Emma Bunton and Victoria Beckham while the then Prince Charles stands nearby

Prince Harry, aged 13, grinning as he meets the Spice Girls during a visit to South Africa, where they were performing a concert, 1997. He clutches the hands of Emma Bunton and Victoria Beckham while the then Prince Charles stands nearby 

Prince Harry, then aged three, sticks his tongue out while being held by his mother, Princess Diana, on the Buckingham Palace balcony during Trooping the Colour in 1988. In front of the pair are Prince William, Lady Gabriella Windsor and Lady Rose Windsor

Prince Harry, then aged three, sticks his tongue out while being held by his mother, Princess Diana, on the Buckingham Palace balcony during Trooping the Colour in 1988. In front of the pair are Prince William, Lady Gabriella Windsor and Lady Rose Windsor

Harry ending his Invictus Games promotion video with the Queen with a hilarious mic drop in 2016

Harry ending his Invictus Games promotion video with the Queen with a hilarious mic drop in 2016

The young prince, then aged five, couldn't resist peeking out of a window at Buckingham Palace during Trooping the Colour in 1990

The young prince, then aged five, couldn’t resist peeking out of a window at Buckingham Palace during Trooping the Colour in 1990

Harry wraps his arm around a wooden skeleton during his time as a student at Eton College, 2003. He studied at the school from 1998, following William who started three years before

Harry wraps his arm around a wooden skeleton during his time as a student at Eton College, 2003. He studied at the school from 1998, following William who started three years before

Harry, wearing a blue school jumper and shorts, peeks through homemade binoculars at photographers after finishing his first day at Mrs Mynor's nursery in Notting Hill, London on September 16, 1987

Harry, wearing a blue school jumper and shorts, peeks through homemade binoculars at photographers after finishing his first day at Mrs Mynor’s nursery in Notting Hill, London on September 16, 1987

Prince Harry smiles as a dinner lady kisses his hand during a visit to the Osmani School in London, September 2002

Prince Harry smiles as a dinner lady kisses his hand during a visit to the Osmani School in London, September 2002

Just six years old, Harry wears a white t-shirt and shorts as he sprints to the finishing line with a big smile during his school sports day on June 11, 1991

Just six years old, Harry wears a white t-shirt and shorts as he sprints to the finishing line with a big smile during his school sports day on June 11, 1991

Say cheese! Harry cheekily squints during a family photo with his parents and brother Prince William at Kensington Palace, December 1986

Say cheese! Harry cheekily squints during a family photo with his parents and brother Prince William at Kensington Palace, December 1986

The young prince grins as he attempts to balance a bucket of water on his head during a visit to the Osmani School in September 2002

The young prince grins as he attempts to balance a bucket of water on his head during a visit to the Osmani School in September 2002

Marking the end of his studies at Eton in 2003, Harry, 18 at the time, smiles next to a bronze statue of Perseus holding the gorgon's head in a garden at the school

Marking the end of his studies at Eton in 2003, Harry, 18 at the time, smiles next to a bronze statue of Perseus holding the gorgon’s head in a garden at the school

Princess Diana closes her eyes and Harry grins as water splashes against the pair while they slide down the Depth Charge ride at Thorpe Park, April 1992

Princess Diana closes her eyes and Harry grins as water splashes against the pair while they slide down the Depth Charge ride at Thorpe Park, April 1992

With 'Wales' written across his head, Harry stands grinning in a diving suit during a visit to the Royal Navy's fleet diving squadron at Horsea Island, October 2007

With ‘Wales’ written across his head, Harry stands grinning in a diving suit during a visit to the Royal Navy’s fleet diving squadron at Horsea Island, October 2007

Prince Charles picks Harry up to place him on the back of a family dog as King Juan Carlos, his wife Sofia, Princess Diana and William look on during a holiday in Palma, Majorca in 1986

Prince Charles picks Harry up to place him on the back of a family dog as King Juan Carlos, his wife Sofia, Princess Diana and William look on during a holiday in Palma, Majorca in 1986

Harry plays with children in South Africa during a visit in 2006 to launch his charity Sentebale. He opens his mouth at a laughing child while another places her hand on his jaw

Harry plays with children in South Africa during a visit in 2006 to launch his charity Sentebale. He opens his mouth at a laughing child while another places her hand on his jaw

Harry wraps his arm around his cousin Zara Tindall's shoulder, giving her an affectionate hug on the wedding day of Peter Phillips and Autumn Kelly at St. George's Chapel on May 17, 2008

Harry wraps his arm around his cousin Zara Tindall’s shoulder, giving her an affectionate hug on the wedding day of Peter Phillips and Autumn Kelly at St. George’s Chapel on May 17, 2008 

Prince Harry can't help but smile as his aunt Princess Anne presents him with an Afghanistan war campaign, May 2008

Prince Harry can’t help but smile as his aunt Princess Anne presents him with an Afghanistan war campaign, May 2008

Anne playfully picks up a young Harry so he can see over the balcony at Buckingham Palace after Trooping the Colour in 1986

Anne playfully picks up a young Harry so he can see over the balcony at Buckingham Palace after Trooping the Colour in 1986

Covered in mud and standing in the pouring ran, Harry grins to his fellow Young England polo players as he waits to receive his trophy after winning a match in 2003

Covered in mud and standing in the pouring ran, Harry grins to his fellow Young England polo players as he waits to receive his trophy after winning a match in 2003

A barefoot Harry, wearing an adorable corduroy dungaree set, takes his first steps at home in the playroom of Kensington Palace in October 1985

A barefoot Harry, wearing an adorable corduroy dungaree set, takes his first steps at home in the playroom of Kensington Palace in October 1985

Harry, wearing a laidback cap, jeans and unbuttoned shirt, seems to find something amusing at the Guards Polo Club in Windsor, 2004

Harry, wearing a laidback cap, jeans and unbuttoned shirt, seems to find something amusing at the Guards Polo Club in Windsor, 2004

Harry, with a mischievous grin, holds a child wearing sunglasses and carrying a lollipop during his visit to Lesotho in 2004

Harry, with a mischievous grin, holds a child wearing sunglasses and carrying a lollipop during his visit to Lesotho in 2004

Prince Harry makes his grandfather Prince Philip laugh as they watch the Rugby World Cup Final, 2015

Prince Harry makes his grandfather Prince Philip laugh as they watch the Rugby World Cup Final, 2015 

Harry, aged eight, smiles while wearing a helmet during a visit with Diana to Germany in 1993

Harry, aged eight, smiles while wearing a helmet during a visit with Diana to Germany in 1993

Prince Harry smiles eagerly alongside his brother Prince William on his first day of prep school, September 1989

Prince Harry smiles eagerly alongside his brother Prince William on his first day of prep school, September 1989 

The young price looks comfortable holding a baby as he makes members of the public laugh during a visit to the University Hospital of Wales in Cardiff in 2008

The young price looks comfortable holding a baby as he makes members of the public laugh during a visit to the University Hospital of Wales in Cardiff in 2008

With a bewildered expression, Harry poses with a copy of Hello! Magazine featuring his brother Prince William and Kate during a visit to University Hospital of Wales on June 5, 2008 in Cardiff

With a bewildered expression, Harry poses with a copy of Hello! Magazine featuring his brother Prince William and Kate during a visit to University Hospital of Wales on June 5, 2008 in Cardiff

Prince Harry, right, playing on a fire engine in Sandringham during an adorable moment with his brother William, 1988

Prince Harry, right, playing on a fire engine in Sandringham during an adorable moment with his brother William, 1988

William, Harry and Philip all laugh while the Queen looks somewhat disgruntled during the wedding of Lady Tamara Grosvenor and Edward Van Cutsem, 2004

William, Harry and Philip all laugh while the Queen looks somewhat disgruntled during the wedding of Lady Tamara Grosvenor and Edward Van Cutsem, 2004

In a sweet father and son moment, Charles zooms down a slope with Harry on a sled during a skiing holiday in Klosters, Switzerland, 1997

In a sweet father and son moment, Charles zooms down a slope with Harry on a sled during a skiing holiday in Klosters, Switzerland, 1997

Harry, wearing a 'Haiti we care' t-shirt, shows off his dance moves at a concert in Barbados in aid of the Haiti earthquake disaster in January 2010

Harry, wearing a ‘Haiti we care’ t-shirt, shows off his dance moves at a concert in Barbados in aid of the Haiti earthquake disaster in January 2010

Harry takes a call and seals a £10billion City deal during a charity day for international brokerage firm ICAP, 2008. He's surrounded by workers in fancy dress

Harry takes a call and seals a £10billion City deal during a charity day for international brokerage firm ICAP, 2008. He’s surrounded by workers in fancy dress 

With a cheeky smile on his face, a 12-month-old Prince Harry shows off his piano skills with Prince William by his side at Kensington Palace in 1985

With a cheeky smile on his face, a 12-month-old Prince Harry shows off his piano skills with Prince William by his side at Kensington Palace in 1985

Prince Harry shows his nurturing side in Barbados and cradles seven-week-old baby Jean-Luc Jordan during a visit to the Queen Elizabeth II Hospital in January 2010

Prince Harry shows his nurturing side in Barbados and cradles seven-week-old baby Jean-Luc Jordan during a visit to the Queen Elizabeth II Hospital in January 2010

After setting off early and winning a race against Usain Bolt, Harry poses with the sportsman and the pair perform the runner's trademark celebration during a visit to Jamaica, 2012

After setting off early and winning a race against Usain Bolt, Harry poses with the sportsman and the pair perform the runner’s trademark celebration during a visit to Jamaica, 2012


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