Now, the third generation leader of the reclusive state appears to have spruced up his international image in a matter of months as he takes leisurely strolls with world leaders and engages in bear hugs. He even has a sense of humor.
"Kim Jong Un is presenting a much more accessible face of the regime to the world, and he's actually been quite clever, I think, in the way he's managed the international image," said Simon Baptist, regional director for Asia at The Economist Intelligence Unit.
That is particularly shrewd as "he has murdered his relative at an international airport, and millions of North Koreans do live in impoverishment, or in prison camps," Baptist told CNBC.
Belying years of international isolation, Kim appeared at ease this week as he interacted with Singaporean government officials including Prime Minister Lee Hsien Loong.