The leaders were later joined by their senior advisers for bilateral talks, with Secretary of State Mike Pompeo and National Security Adviser John Bolton sitting to the left of Trump. "We have our hostages, testing, research and all missle launches have stoped, and these pundits, who have called me wrong from the beginning, have nothing else they can say!" Trump then directed Kim to walk down a hallway, where they briefly spoke.
After greeting each other, the two leaders planned to sit for a one-on-one meeting that a United States official, speaking on condition of anonymity, said could last up to two hours, with only translators joining them.
Entering their meeting, Trump said that he "feels really great".
"It was not easy to get here", he said.
North Korea, however, has shown little appetite for surrendering nuclear weapons it considers vital to the survival of Kim's dynastic rule.
Still, the sense of anticipation was great in Singapore, with people lining spotless streets holding cellphones high as Trump headed to meet Lee.
About 5,000 journalists are in Singapore for the occasion, but only a handful of American and North Korean reporters and photographers were permitted at the venue when the two leaders greet each other. Sitting next to the president, Kim said both leaders "decided to leave the past behind" and that "the world will see a major change".
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Mr. Trump and Mr. Kim are both looking for political victories that will help them at home.
"I believe we're going to have a terrific success or a modified success", Trump said during a press conference last week with Japanese Prime Minister Shinzo Abe.
Kim has rejected calls to unilaterally give up his weapons in return for economic aid, and instead has proposed a step-by-step denuclearization process.
Here's a look back at some of the many comments Trump has shared on Twitter about the North Korean leader.
It's so far unclear whether the US and North Korea will release some kind of joint statement or agreement following the sit-down.
"North Korea has previously confirmed to us its willingness to denuclearize, and we are eager to see if those words prove honest", Pompeo said.
But in return, Washington would offer "different and unique" guarantees "to provide them sufficient certainty that they can be comfortable that denuclearisation is not something that ends badly for them".
The president is set to meet with North Korean leader Kim Jong Un on June 12 in Singapore.