Yes, because it fits with his short hamster-on-speed attention span. A dictator can catch Trump off guard flatter him and get whatever he wants in under five minutes.
Have you read the anecdote about he startled Chancellor Merkel by offering Germany “the best ever trade deal right now” should they leave the EU. Merkel patiently tried to explain to Trump the basics - the fundamental concept of EU as a unified free trade area, the ratification of such deals by EU-wide legislative bodies and so forth and Trump trailed off after a few minutes.
The dictator, whether it’s MBS, Putin, Erdogan or Duterte is all branches of government embodied in one individual and can provide snap feedback to Trump’s hare brained ideas, like a toadying aide, leading clueless Trump (and the US) down the worst possible path.
I’m a relatively sane person who doesn’t subscribe to conspiracy theories, except one - that MJ is being legalized to sedate the population now that alcohol is slowly getting out of fashion. As you’ve correctly pointed out, stoners do not start revolutions.
Kim is intentionally keeping his people starving - there’s an harrowing scholarly opus on how the NK regime weaponized starvation against its own people, and they weren’t the only ones - Mariam in Ethiopia (you know the Live Aid thing), al-Bashir in what is now South Sudan, Mugabe in Zimbabwe…