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President Obama’s decision to sing “Amazing Grace” at the end of his eulogy for the Rev. Clementa Pinckney, a black pastor who was killed with eight others during Bible study in a Charleston, S.C., church last month, became one of the more memorable moments of his second term. But the idea raised at least some eyebrows when he first broached it with his closest confidants.

Mr. Obama was on the Marine One helicopter leaving the White House en route to Andrews Air Force Base for his flight to South Carolina when he mentioned the thought to Michelle Obama and Valerie Jarrett, their close friend and a White House senior adviser.

“When I get to the second part of referring to ‘Amazing Grace,’ I think I might sing,” he told them, by Ms. Jarrett’s account.

“Hmm,” Ms. Jarrett recalled responding.

Mrs. Obama was a little more pointed. “Why on earth would that fit in?” she asked.

He tried to explain. “I don’t know whether I’m going to do it,” he said, according to Ms. Jarrett, “but I just wanted to warn you two that I might sing.” He added, “We’ll see how it feels at the time.”

Ms. Jarrett told the story at the Aspen Ideas Festival last week in a session with Walter Isaacson, the Aspen Institute president. She noted that she had a little history with Mr. Obama’s singing career, recalling the 2012 fund-raiser at Harlem’s Apollo Theater when he crooned a little Al Green.

“I will confess to you that I was the voice back stage when he was being egged on by the electrical engineers who were doing the sound work for the show, ‘Go on, Mr. President, sing, sing,’” Ms. Jarrett said, referring to the 2012 event at the Apollo. “And I said, ‘Don’t sing! Don’t sing! Please, whatever you do, don’t sing.’ And of course, he sang. And it went over very well.”

So this time, she said, she knew better than to object and, in fact, in an email on Monday she said she and the first lady “both encouraged him to do whatever the spirit moved him to do.”

Many who watched him that day noted that he paused a long time before beginning to sing.

“So later I said to him, ‘Were you thinking about whether or not to sing?’” Ms. Jarrett recalled at Aspen. “He said, ‘Oh no, I knew I was going to sing. I was just trying to figure out which key to sing it.’”