I was hopeful back then that the ping-ping diplomacy of American violinists could lead to the kind of rapprochement that the ping-pong diplomacy of the 1970s brought with China.
It turned out that my hope was entirely misplaced. But could this time be different?
Six months after the New York Philharmonic visited Pyongyang, Kim Jong Il had a debilitating stroke and the regime started preparing for a second transition of power in the world's only communist dynasty.
That put the regime on a course that involved more nuclear weapons tests and the revelation of a huge uranium-enrichment facility, then the coronation of the inexperienced 27-year-old "Great Successor" as leader at the end of 2011.
Kim Jong Un's first six years in power were marked by a crackdown on the borders and even more brutal repression. And last year came a thermonuclear bomb, a salvo of increasingly advanced missiles and a relentless barrage of threats.
But, despite everything I've learned in the 14 years since I began covering North Korea, despite myself, I feel hopeful again now ahead of today's summit between US President Donald Trump and Kim.
I'm not optimistic about complete denuclearisation. No way.
Kim is highly unlikely to give up his nuclear programme anytime soon, no matter what he agrees to today.
The now 34-year-old dictator is consumed by a need to prove he is the legitimate leader of the country his grandfather founded seven decades ago. He is, after all, a marshal who has never served a day in the military, and the nuclear weapons programme is, in the regime's words, his "treasured sword."
Cynicism and pessimism have always served North Korea watchers well, and it remains fashionable in the Washington twitterati to hark back to the failed agreements of 1994 and 2005.
Certainly, the task of denuclearisation is much more difficult now than it was in 2005, before North Korea had conducted its first fizzle of a nuclear test.
But this moment feels different. This process is different. These leaders are different.
From the outside, people tend to look at North Korea as a monolith, stuck in a time warp somewhere between the Victorian era and Stalin's heyday. People tend to look at the leaders called Kim as if they were printed in triplicate.
But the North Korea of 2018 is not the North Korea of 1998, when a famine was rampaging through the country, killing maybe two million people.
It is not even the North Korea of 2008, when the regime went into stabilisation overdrive. That North Korea was a country where poverty and malnutrition were more or less equally shared, in good socialist style. A country where people might have had an inkling that the outside world was a better place, but many could not say for sure.
In fundamental ways, North Korea is beginning to change.
For all the communist central planning, North Korea is essentially capitalist now. More than half of North Koreans earn their living in the market economy, and the vast majority of the remainder have some involvement in private enterprise.
"No one expects the government to provide things anymore," one escapee from North Korea, who was a university student when Kim Jong Un took over, told me last year. "Everyone has to find their own way to survive."
It is no longer the cliched "Hermit Kingdom," either. Yes, the regime does its best to cut off all information from the outside world, and there is still no Internet, but almost every one of the scores of escapees I've met has watched melodramatic South Korean soap operas or Chinese action movies. They know they do not live in a paradise, as the regime has long told them.
And those who say that Kim is just taking a leaf from his father's playbook are overlooking demonstrable differences in their style.
Kim Jong Il was an introverted, reluctant leader who seemed to hate having to leave his palaces, stacked with DVDs and cognac. In 17 years in power, he spoke in public only once, and even then briefly. He went to China and Russia grudgingly to keep his patrons happy.
In stark contrast, Kim Jong Un is a charismatic leader who has delivered numerous public addresses and seems to relish being out and about, whether it's at a missile launch or at the opening of a factory producing Hello Kitty-style backpacks. He is tactile, hugging his nuclear engineers and the South Korean president with almost equal fervour.
Kim exudes confidence and has shown himself to be entirely unconcerned with global norms and their consequences.
His army of cyberwarriors attacks banks and hospitals and movie production companies. He had his uncle and his half brother killed. He sent a young American man, who had gone to North Korea in perfect health, home in a coma to die.
Clearly, he is capable of great brutality.
But he appears to be thinking rationally about what he needs to do if he is going to stay in power. Killing your uncle and brother makes perfect ruthless sense if you're a totalitarian dictator who needs to eliminate potential rivals.
That is what he is doing now. He is thinking in decades, not in years.
If he lives as long as his father, who died of a suspected heart attack at age 70, Kim could have another 37 years on this planet, although diabetes or heart disease would seem to be risks for the clearly overweight leader.
He knows if he is to retain control of his anachronistic throwback of a country, it is not enough to take care of the 1 per cent who keep him in power. He also needs to devote some energy to the 99 per cent, the people he told would never have to tighten their belts again.
Those people need to feel like their lives are improving, too. And while Kim has muddled through until now, it is impossible to achieve the kind of growth he wants while sanctions are being applied with Trump's "maximum pressure."
As North Korea's state media illustrated in full Technicolour yesterday, he is committed to having a successful summit.
North Korea's most authoritative anchor appeared on state-run Korean Central Television to announce that Kim had departed for a "historic meeting" with "American President Donald J. Trump." This was a rare neutral mention of the US leader, who is more frequently called a "dotard" or "senile" in state propaganda.
The Rodong Sinmun newspaper carried an editorial explaining that "even if a country had a hostile relationship with us in the past, our attitude is that if that country respects our autonomy . . . we will seek to normalise relations through dialogue."
Played right, this could be an opportunity for the outside world to alleviate the plight of the 25 million North Koreans who are trapped in Kim Jong Un's prison state, the people who are subject to his threats on a daily basis.
Hoping for regime collapse or pushing for regime change has not worked. This is an opportunity to use diplomatic engagement with North Korea to benefit both the outside world and those on the inside, said Sokeel Park of Liberty in North Korea, a group that helps people who have escaped from North Korea.
Accelerating the opening and normalisation of North Korea as a country could help make life more open and more normal for North Koreans who live without basic rights such as speaking and traveling and loving freely.
This will be difficult. Kim Jong Un may be game for some economic change, but he will certainly resist political changes that could weaken his grip on the state.
Still, in so many ways, this millennial is ready to do things differently. Trump has also shown a willingness to do things differently.
This is not 1994. This is not 2005. This is 2018.