London CNN  — 

For many Britons, the defining characteristic of Prince Philip was not his public service or his royal standing, but his propensity to make unscripted, off-the-cuff and sometimes wildly inappropriate comments.

The longest-serving consort in the history of the British monarchy died aged 99 on Friday, leaving behind a lengthy catalog of provocative remarks that cemented his reputation as an outspoken royal, untamed by the family’s carefully rehearsed public image.

Viewed charitably, those utterances could be seen as examples of a mischievous British sense of humor.

In 2011, then-Prime Minister David Cameron paid tribute to Philip’s wit, saying: “Humor is a great part of British life and we thank the duke for his unique contribution.”

But some comments from the prince strayed undeniably into the realm of casual racism.

During a royal visit to China in 1986, for instance, Philip described Beijing as “ghastly” and told British students: “If you stay here much longer you’ll all be slitty-eyed.”

He also quipped: “If it has four legs and is not a chair, has wings and is not an aeroplane, or swims and is not a submarine, the Cantonese will eat it.”

Queen Elizabeth ll and Prince Philip visit the Great Wall of China in 1986.

Remarks like those threatened to turn him into a caricature, and the China comments were so ill-judged that they were a scandal even at the time.

But as the years have passed, his reputation has softened and some of his more problematic comments have faded in the collective British memory.

“He was a throwback to old-school racism. Painting him as a benign, cuddly uncle of the nation is simply untrue,” said Kehinde Andrews, Professor of Black Studies at Birmingham City University, on Friday.

“When he says things about Chinese people’s eyes and chucking spears, it’s very ugly and would not be tolerated anywhere else nor from anyone else,” Andrews told CNN.

A long history of controversial remarks

Even as a lifelong royal who married into the British monarchy more than seven decades ago, Philip retained a reputation as something of an outsider.

He often flashed a self-deprecating humor that went down well at official occasions. “My generation, although reasonably well-schooled, is probably the worst educated of this age,” he said at one such event.

“Don’t ask me to explain why it is that (the Queen) has an official birthday in June, when her proper birthday’s in April – you’ll just have to accept it,” he said at another.

That reputation as a maverick was sometimes further boosted by his off-hand comments, which frequently dominated headlines on official trips and were occasionally picked up when the duke believed he was out of earshot.

In 1995, Philip riffed on a British stereotype that Scots enjoy a drink, asking a driving instructor in Scotland: “How do you keep the natives off the booze long enough to pass the test?”

He also became an unlikely public voice during the debate over gun control in Britain in the mid-1990s, which broke out after a shooting at Dunblane Primary School in Scotland left 16 dead.

“If a cricketer, for instance, suddenly decided to go into a school and batter a lot of people to death with a cricket bat, which he could do very easily… I mean are you going to ban cricket bats?” he said on BBC radio. It was an extraordinary intervention, as senior royals are expected to remain resolutely apolitical.

Sometimes, a comment from the prince presented royal officials with public relations fires that required rapid extinguishing. He came across as out-of-touch and aloof – a charge the royals have often faced – when he told NBC’s “Meet the Press” in 1969 that the monarchy was running out of money, and that its members might have to move to smaller premises.

But it was his comments about other nationalities – often inappropriate, occasionally racist and sometimes made on visits hosted by the nations who were the subject of them – that most complicate his legacy.

During a 1998 conversation with a British student who had been trekking in Papua New Guinea, Prince Philip asked: “You managed not to get eaten, then?” – an apparent reference to the historic belief that cannibalism had been practiced on the South Pacific islands.

In 2002, he shocked a Bangladeshi teenager at a London youth club by saying the 14-year-old “looks as if he is on drugs.” The same year, he is reported to have asked Australian Aborigines: “Do you still throw spears at each other?”

A year later, the Queen and Prince Philip went to open the Commonwealth Heads of Government Meeting in Nigeria. It was the Queen’s first visit in 47 years. Greeted by Nigeria’s then-President, Olusegun Obasanjo, who was wearing traditional robes, Philip quipped: “You look like you’re ready for bed.”

Prince Philip toasts then-Nigerian President Olusegun Obasanjo in  Abuja in 2003.