He wowed her with a rousing solo rendition of O Canada. He made her laugh when he swore at the ceremony marking the patriation of the Canadian constitution. He happily allowed her to practice her excellent French over lunch.
And Monday, Queen Elizabeth acknowledged the affectionate relationship she has forged with Jean Chretien over five decades by appointing him to the exclusive Order of Merit, Canada's highest civil honour.
The two first met during Canada's Centennial Year in 1967 when he was a junior minister and she was a young Queen. But it was during the Queen's nearly week-long visit to northern Canada in 1970 that they really got to know each other.
Mr. Chretien, then the Minister of Indian and Northern Affairs, and his wife, Aline, played host to the Queen, Prince Charles, and Princess Anne. He recalled Monday that at one stop the program required they sing O Canada but the master of ceremonies was "too shy" to sing.
"So I went to the mike and there was 3,000 people, the TV, the radio, and I started to sing O Canada but I sang O Canada in those days only in French," he said. "But nobody came along. I was sweating. But anyway, how many of us have been soloists for the royal family?
Prince Charles was in Canada again a year later and met Mr. Chretien at a function. He called him by his first name and told him that his "singing of O Canada in the north last summer is part of the royal folklore," Mr. Chretien said.
Mr. Chretian also recalled how he swore under his breath in front of the Queen when, during the 1982 Parliament Hill signing ceremony of the Constitution Act, Prime Minister Pierre Trudeau broke the tip of his fountain pen. Mr. Chretien was to sign next but there was no ink in the pen, provoking him to swear, "merde."
"The Queen had a big laugh," said Mr. Chretien, who for years kept it a state secret when asked by reporters what caused the laughter. But she knew exactly what he had said.
After becoming prime minister in 1993, Mr. Chretien and his wife met with the Queen and the Queen Mother at the royal Sandringham estate. During their lunch, the Queen and Queen Mother spoke only in French and the Queen Mother regaled them with stories of her visit to Montreal in 1939.
Mr. Chretien said their French was very good. "They always told me they enjoyed the occasion to practice their French," he said.
The Order of Merit has only 24 members at one time; vacancies are created when a member dies. Since it was founded in 1902 by King Edward VII, there have been only 169 members. Mr. Chretien joins former South African leader Nelson Mandela and former British Prime Minister Margaret Thatcher, who are current members. Florence Nightingale was a member, as were T.S. Eliot, Winston Churchill, Mother Teresa and Dwight D. Eisenhower.
Christopher McCreery, an expert and author on Canadian decorations, said the Order of Merit is "the most senior honour a Canadian can receive." It is ahead even of the Order of Canada.
"I was thrilled," Mr. Chretien said Monday about a telephone call three weeks ago from the Queen's private secretary informing him of the award, a personal gift of the sovereign. "Apparently it's the biggest one. It's a very rare honour and it is a personal gift of her majesty. I'm very grateful and very honoured."
Mel Cappe, the former Canadian High Commission to Britain, remembered yesterday receiving a call from Buckingham Palace in 2005 in which he was told the Queen was thinking of appointing Mr. Chretien to the Order of Merit. He said that Mr. Chretien would be very honoured.
"It's one of these things that there isn't a recommendation for. It really comes at the initiative of the Queen," said Mr. Cappe. "She had this personal affection for Chretien ... She has a mind of her own on these things and is a good judge of character."
Mr. Chretien has not spoken to the Queen about his award. He said he thinks he last saw her in Nigeria in 2003. No date has been set yet for receiving his award.