Prince Philip is easily Britain's most blundering royal, but he's certainly not the only member of the monarchy to make a public blooper. To mark the Duke of Edinburgh's 90th birthday, TIME takes a look at some of the royal family's biggest gaffes

Prince Charles Holds the Press in Contempt
Prince Charles
© Tim Graham / Getty Images

In 2005, more than 50 journalists gathered at Klosters, a Swiss ski resort, for a photo call marking Prince Charles' imminent wedding to Camilla Parker Bowles. During the shoot, Charles couldn't hide his contempt. "I hate doing this ... I hate these people," he muttered to his sons Harry and William, unaware that his microphone was picking up every word. Asked by the BBC's royal correspondent Nicholas Witchell how he felt about his upcoming nuptials, Charles responded sarcastically, "I'm very glad you've heard of it, anyway." He then turned his head slightly toward Harry and whispered, "Bloody people. I can't bear that man. He's so awful, he really is."

Princess Anne Insults a Fan
Princess Anne
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On Christmas Day 2000, 75-year-old pensioner Mary Halfpenny spent three hours making a flower display for the Queen Mother, then waited patiently outside a church on Sandringham Estate - one of the royal family's country homes - hoping to present it to her. The exchange never happened. Instead, Princess Anne, Queen Elizabeth II's only daughter, grabbed the bouquet and huffed, "What a ridiculous thing to do!" The incident left Halfpenny reeling. "It was a really hurtful thing to say," she told reporters. "I've made baskets of flowers for the Queen, and she has always said how nice they are." And Anne's un-princesslike attitude didn't end there: she reportedly told her nieces, princesses Beatrice and Eugenie, to "get a move on" and discouraged them from accepting flowers from well-wishers.

Prince Philip's Lame Lockerbie Lament
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The 1988 bombing of Pan Am Flight 103 killed 259 passengers and crew members; in addition, large sections of the plane crashed into homes in Lockerbie, Scotland, killing 11 residents. In 1993, as he was visiting the street where the victims on the ground died, the prince shocked locals by comparing their tragedy to problems at the royal estate. "People usually say that after a fire, it is water damage that is the worst," he said. "We are still trying to dry out Windsor Castle."

Harry and the Embarrassing Home Video
Prince Harry
© Dan Kitwood / Getty Images

In 2009, the British tabloid News of the World leaked a video in which Harry refers to his South Asian army comrades using racist language. Worse, the video had been filmed by the prince himself three years earlier. Touring a room while his friends doze, he describes one officer as "our little Paki friend Ahmed," employing a derogatory term for a Pakistani. Later, he spots a colleague wearing camouflage netting over his head and says, "It's Dan the Man ... you look like a raghead." Prince Harry's spokesman fended off claims of racism. "Prince Harry used the term raghead to mean Taliban or Iraqi insurgent," he said. As for Ahmed, the spokesman claimed that Paki was merely his nickname.

Prince Edward's Marketing Adage: Death Sells
Prince Edward

In 2006, a 17-year-old Australian schoolboy taking part in the Duke of Edinburgh adventure scheme - a program that encourages young people to participate in volunteer work, sports and expeditions - died while trekking unsupervised through the bush. Three years later, reporters in Australia asked Prince Edward - the Queen and Philip's youngest son, and the chairman of the scheme - about the incident. He couldn't recount the specific circumstances; however, he did suggest that the death of a British boy in 1956 had boosted the popularity of the program. "Obviously we don't want that to happen ... [But its] reputation among young people was, 'Wow, this is serious. You could die doing this.' "

Charles and Those Four Little Words
Princess Diana and Prince Charles
© Bob Thomas / Popperfoto / Getty Images

Royal weddings make the public giddy with notions of fairy tales and enduring love. For Prince Charles, however, marrying Lady Diana Spencer involved less romance and more hand-wringing. An engagement-day interview in 1981 revealed just how bad he was at concealing his unease. Asked if they were in love, Diana - just 20, and 12 years Charles' junior - responded, "Of course!" But Charles' follow-up suggested otherwise: "Whatever 'in love' means."

Sarah Ferguson and the 'Fake Sheik'
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© Eamonn McCormack / WireImage / Getty Images

She's been ridiculed as the Duchess of Pork for her work with Weight Watchers, and a photographer once snapped a shot of a man sucking her toes. But nothing could have prepared Duchess of York Sarah Ferguson for the embarrassment that followed a sting operation launched by the News of the World in May 2010. The tabloid secretly filmed Fergie demanding a payment of ยฃ500,000 (about $820,000) from an undercover reporter posing as a wealthy Arab businessman. In exchange, she promised access to her ex-husband Prince Andrew, a U.K. trade envoy. "That opens up everything you would ever wish for," she's heard saying on the tape. "I can open any door you want, and I will for you. Look after me and he'll look after you ... you'll get it back tenfold."

Andrew and the WikiLeaks Leaks
Prince Andrew
© RoyalPress Nieboer / dpa / Corbis

British trade envoy Prince Andrew has proved he can sully his reputation without any help from ex-wife Fergie. In November 2010, WikiLeaks published cables from Washington's ambassador to Kyrgyzstan that describe how Andrew spoke "cockily" at a two-hour lunch in Bishkek. He said Americans "know nothing about geography," dismissed the "idiocy" of Britain's anticorruption officials and denounced "those [expletive] journalists ... who poke their noses everywhere" as part of bribery investigations, thereby making it tough to conduct business. When one businessman suggested that only those willing to participate in corruption could make money, the prince reportedly responded, "All of this sounds exactly like France."

Prince Harry Goes Nazi
Prince Harry
© Reuters / Corbis

In 2005, just two weeks before Holocaust Memorial Day, Prince Harry figured it was a good idea to turn up at a "colonials and natives" costume party dressed as a Nazi. British tabloid the Sun published a photo of the prince wearing a swastika armband and a desert uniform similar to those worn by Erwin Rommel's German Afrika Korps. "I'm very sorry if I have caused any offense," the prince said in a statement. "It was a poor choice of costume, and I apologize." He probably should have taken tips from his scandal-free brother - Prince William reportedly wore a homemade outfit representing lions and leopards.

Prince Philip on How to Offend Australia's Aborigines
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© Torsten Blackwood / AFP / Getty Images

As part of the Aboriginal rights movement, Australia's Aborigines seek freedom from oppression and poverty and hope to cast off the stereotype that they're warring tribesman. Prince Philip clearly missed the memo. During a visit to the Aboriginal Cultural Park in Queensland, Australia, in 2002, he asked successful Aboriginal businessman William Brin, "Do you still throw spears at each other?" Once again Buckingham Palace was left to clean up the mess. "They were lighthearted comments," a spokesman said. "There was no offense intended."