Princess Diana was known for many things. Grace, fashion, charity work. But behind palace doors, she also had a side that was delightfully mischievous. From fake vomit pranks to risqué birthday cards, the late Princess of Wales reportedly had a wicked sense of humor that kept those around her constantly on their toes.
Now, celebrity hairstylist Sam McKnight, whose A-list clientele includes Kate Moss and Naomi Campbell, is sharing some of his favorite, laugh-out-loud memories with Diana. McKnight first met the princess during a 1990 photo shoot when he was hired to style her hair.
He told The Telegraph, “Princess Diana comes bouncing up the stairwell…She stuck out her hand with a big smile and said, ‘Hi, I’m Diana.'” That simple moment sparked a professional relationship that lasted seven years.
Princess Diana runs in the mother’s race on Sports Day at Prince Harry’s school, 1991.pic.twitter.com/zk2twp7ijt
— Interesting things (@awkwardgoogle) May 10, 2025
Recalling the experience, McKnight added, “I was back and forth between London and New York working—in between she’d often have a sneaky perm.” But it was Diana’s sense of humor that left a massive impression. “She was so funny,” McKnight said. “She sent [me] these really filthy birthday cards from this card shop on Kensington High Street.”
That kind of cheeky behavior wasn’t reserved just for close staff. Diana famously played pranks on her sons too, once surprising a young Prince William by inviting supermodels over when he was home. She was also known to trick staff members using fake vomit for laughs.
McKnight admits her playful charm was unmatched. “There’s never really been a replacement [for her].” He added, “That’s the wrong word. No one has ever fitted into that spot she created, there’s been a void there.”
Diana, the late Princess of Wales, was a beacon of compassion and empathy.
With unwavering dedication, she fearlessly addressed numerous humanitarian causes, including those related to children, homelessness, people affected by HIV/AIDS, and victims of landmines.
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— Dr Tessy Ojo CBE (@Ttall) June 29, 2023
Turns out, sending naughty cards was something of a Diana signature. In 2023, a pair of greeting cards sent by the princess to Greece’s former King Constantine II were auctioned for nearly $8,700. One card read, “I couldn’t decide which card to send and then thought you’d enjoy both!” Each was decorated with suggestive cartoons and punchlines.
Hairstylist Richard Dalton, who also worked closely with the princess, echoed the sentiment. Speaking to People, he shared, “Her jokes were hysterical…very naughty at times.” He described Diana’s humor as “amazing, wicked.”
Whether through sneaky perms or scandalous birthday cards, Princess Diana’s legacy isn’t just one of elegance, but also of laughter, boldness, and an unforgettable sparkle of mischief!
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