Britain’s Prince Philip, who died Friday at age 99, was well known for his wit, sharp tongue and excruciating comments.

Even when he retired from public life, at 96, he did so with a trademark quip. At a reception with Philip, also known as the Duke of Edinburgh, and his wife, Queen Elizabeth II, a guest said he was sorry to hear the duke was standing down.

Philip replied: “Well, I can’t stand up much!”

It was said that he made the queen laugh. He also seemingly acknowledged that he tested her patience.

“You can take it from me, that the queen has the quality of tolerance in abundance,” he once said in a speech, prompting chuckles from the crowd and the tiniest of smiles from his wife. Their marriage was the longest in British royal history. The queen once said of her husband, “He has, quite simply, been my strength and stay all these years.”

Philip was outspoken, direct and often veered wildly beyond what many believed was appropriate.

In her book “The Wicked Wit of Prince Philip,” the author Karen Dolby writes, “Prince Philip has not always been popular with liberals. But then he’s never tried to be.”

During his long life in a very public role, it’s hard to think of a group of people he did not offend — at home or abroad.

Here are some of his more notorious comments:

During a 1986 visit to China, he told a British student: “If you stay here much longer, you will go home with slitty eyes.”

To a driving instructor in Scotland in 1995, he said: “How do you keep the natives off the booze long enough to get them through the test?”

He once asked President Barack Obama, who was talking about world leaders, “Can you tell the difference between them?”

When he shook hands with Malala Yousafzai, the Nobel Peace Prize winner who campaigns for education rights, he could be heard saying: “There’s one thing about children going to school: They go to school because their parents don’t want them in the house.”

Britain's Prince Philip, husband of Queen Elizabeth II, died at age 99 on April 9 at Windsor Castle. (Alexa Juliana Ard/The Washington Post)

During a trip to Canada in 1976: “We don’t come here for our health. We can think of other ways of enjoying ourselves.”

To a group of female Labour Party lawmakers during a reception at Buckingham Palace: “Ah, so this is feminist corner then.”

Speaking to the Welsh singer Tom Jones after his Royal Variety performance: “What do you gargle with? Pebbles?”

To residents of the Cayman Islands, he said: “Aren’t most of you descended from pirates?”

During a trip to a Bangladeshi youth club in central London in 2002: “So who’s on drugs here? … He looks as if he’s on drugs.”

During a 2002 visit to Australia, he asked a group of Indigenous Australians: “Do you still throw spears at each other?”

On a 1963 trip to Paraguay, he told military dictator General Alfredo Stroessner, “It’s a pleasure to be in a country that isn’t ruled by its people.”

When he met Nigeria’s president, who was wearing traditional robes, he declared: “You look like you are ready for bed.”

He asked the actor Simon Pegg, at the London premiere of “The Chronicles of Narnia,” “When did you first realize you had the voice of a mouse?”

During a 2010 visit to the United Arab Emirates, the duke asked a group of expats: “Are you running away from something?”

He told the Australian comedian Adam Hills, who has a prosthetic foot: “You could smuggle a bottle of gin out of the country in that artificial foot.”

After looking at businessman Atul Patel’s name badge at a reception at the palace for British Indians, the duke said: “There’s a lot of your family in tonight.”

On a visit to north London, he asked a disabled man on a mobility scooter: “How many people have you knocked over this morning on that thing?”

At a reception at Buckingham Palace, he asked Stoke-on-Trent lawmaker Joan Walley what area she represented. When she said “Stoke,” the duke replied: “Ghastly place, isn’t it?”

On his daughter, Princess Anne: “If it doesn’t fart or eat hay, she isn’t interested.”