Prince Harry is hitting a major birthday milestone on September 15, as he turns 40.

Born on September 15, 1984, Harry is the younger son of and the late , and he is expected to celebrate entering his fifth decade alongside wife and the couple’s two children, and , at their home in Montecito, California.

Harry was born third in line to the British throne and while this position has moved down to fifth place with the births of his nephews and niece, Harry continues to be a prominent public figure, pursuing private philanthropic and entertainment industry ventures.

The prince has become one of the most photographed people in the world, resulting in a catalogue charting his milestone celebrations, as well as his everyday life.

Well-known for his sense of humor, Harry’s interactions with members of the public, whether at charity engagements or high-powered events, have regularly made headlines and on social media.

Here, to celebrate Harry’s 40th birthday, Regalrumination.com takes a look back at some of his cheekiest moments caught on camera.

Little Prince

Prince Harry’s first photo sessions were taken at Kensington Palace where the then Prince Charles and Princess Diana lived prior to their separation in 1992.

During a December 1986 portrait sitting, Harry broke into a fit of giggles that was captured on camera by photographer Tim Graham.

Mommy’s Boy

There are numerous photos of Harry and his mother, Princess Diana, taken in the years before her , which show their fun-loving dynamic and equal tendency to lapse into cheeky outbursts.

In April 1992, the prince and princess were photographed together riding a water attraction at an English amusement park, Thorpe Park, both in fits of laughter.

Family Joker

Harry was known to the public as the royal family joker, often photographed swapping jokes or humorous comments during official engagements.

In a 2000 photo call during a skiing vacation with William and Charles, Harry was photographed mid-conversation with his grinning brother.

Balcony High Jinks

One location where Harry was regularly photographed engaging in a cheeky moment or two was on the balcony of Buckingham Palace, where thousands of well-wishers and media lenses were present.

In 2005, Harry was photographed pointing out something humorous on the palace forecourt below the balcony to

Brotherly Love

Though Harry’s relationship with his brother, William, has become increasingly focused on since their , the pair enjoyed several touching and light-hearted moments together in public growing up.

During a royal walkabout in 2008, Harry was presented with a magazine featuring William on the cover which he responded to with joking disgust.

Military Man in His Element

Prince Harry after leaving school and has maintained strong relationships and formal associations with military charities and veterans in the years since his 2015 retirement.

In 2010, the prince was photographed broadly smiling as he inspected a Fuchs armored vehicle during a visit to RAF Honington in England, looking at the gathered media pack from behind a mounted rifle.

Fun Cousin

When , Harry took on a senior role in the wedding party, standing beside his brother at Westminster Abbey and later helping to corral the pageboys and flower girls back to Buckingham Palace.

Harry rode in the wedding carriage procession with some of the younger participants, including his cousin, Lady Louise Windsor, who he was photographed with waving to the gathered crowds.

Laughing Royals

Harry wrote about his relationship with sister-in-law Princess Kate in his 2023 saying that he liked “making her laugh” and was “quite good at it.”

In 2014 this was on full display during the Trooping the Colour celebrations in London, as the prince had Kate in peels of laughter on the balcony of Buckingham Palace during the military flypast.

Awkward

Though the business of royalty is often viewed as a wholly serious endeavor, Harry strove to inject a sense of informality and levity into his engagements.

During his 2016 tour of the Caribbean on behalf of , he was photographed pulling faces at photographers in Antigua and Barbuda.

A Grinning Royal Engagement

Harry met future wife Meghan Markle in 2016 and the couple announced their engagement a year later in the gardens of Kensington Palace.

During the engagement photo call, Harry and Meghan exchanged brief comments that inspired a pair of matching smiles, which made the front pages of a number of world newspapers the next day.

Anything Goes

Always one to muck in, Harry has participated in a number of activities during official events, including sports challenges and acting exercises.

In 2020, one of his last engagements as a working royal before his move to the U.S. with Meghan Markle was an Invictus Games event at the famous Abbey Road music recording studios in London.

During the event, Harry recreated the famous Beatles album cover pose on the crosswalk outside the studios, being joined by singer Jon Bon Jovi who also attended the event, and members of the Invictus Games community.

Always Time For Dancing

In their post-working royal lives, Harry and Meghan have embarked on new independent careers as philanthropists and entertainment industry professionals.

In August 2024, the couple received an official invitation to tour Colombia by the country’s vice president and during their stay were photographed in a number of light-hearted moments.

During a visit to the city of Cali, the royal couple were invited to take to the dance floor with Harry gladly taking the opportunity to and get involved.

Do you have a question about Charles and Camilla, Prince William and Princess Kate, Meghan Markle and Prince Harry, or their family that you would like our experienced royal correspondents to answer? Email Support@regalrumination.com. We’d love to hear from you.