I don't know what stupid takes I had then, but I'm hoping I thought that Obama was a longshot to be widely remembered in 2000 years.
Hitler is still a top candidate, in the same way that we remember Nero even if you forget/don't know the specifics. Some people persevere throughout history because the narrative is easy to spell with them.
Mahatma Ghandi is a candidate, if you have to take a guess given the size of the Indian diaspora and if you're placing bets on which current nation-state exist today, betting on India existing in 2000 years is as good a guess as any other.
What's important to remember, though, is how people's collective memory of a person changes throughout history. The mentions of Elon Musk are a good example, but not so much of Elon being remembered (he won't be) but... Elon's company is named after Nichola Tesla, a guy who if you asked if he was going to be some widely remembered inventor in, say, 1920 -- one hundred years ago -- most people would have said no. Sure, he was a known person for people who really followed the invention of alternating current or the race between Westinghouse and Edison, but the Tesla name is more well known today ... He's been resuscitated a bit in the last 20 years through popular re imagination (Nichola Tesla himself was a bit ... mad ... in his old age, claiming to have invented a death ray that would end all wars [this in the interbellum period between WW1 and WW2 would have been handy to the millions who would die...] and a device that could level the Empire State Building, and other pretty wild claims), Edison's is seen more critically than he was 100 years ago, and while Westinghouse has all but been forgotten today by most average people (weirdly, I grew up with a Westinghouse TV, a brand I'd eventually associate with being a cheap store brand), the name Tesla is most well known because of Elon Musks' company... a company that has nothing to do with Nichola Tesla.
So I think it's really tough to take someone like Steve Jobs and say "This guy will be remembered!" Who knows, maybe Jobs will be remembered not for Apple Computer, the iPhone, or Pixar, but maybe he'll be remembered because some eccentric billionaire will found a company in 2120 called "Jobs" and they'll make nuclear-powered sex robots.
Mind you, also, that a lot of the people we remember today from 2000 years ago, notably Jesus, Julius Caesar, Alexander the Great, not all of them were very well known to their contemporaries or immediate contemporaries. Jesus is much more ubiquitous today than in the first 200 years after his death; Most of what we popularly "know" about Julius Caesar was constructed by William Shakespeare and today the person of Julius Caesar and the character of Julius Caesar are so intertwined that it's difficult to separate them. So, who knows, maybe someone in 1500 years after Obama's life creates the equivalent of Shakespeares' Julius Caesar about Obama, and the understanding of Obama in 4020 is influenced more by that artist's reappropriation of him as a theatrical character than the actual historical figure himself.
