Ah, I see the argument here. To be fair, there is truth to the notion that voter choice is driven by more than entertainment. The retort is correct in saying that political experience and policy positions matter, and of course Hillary did receive more popular votes in 2016. But what is often forgotten is that, according to journalist Robert Draper, a significant reason she lost was the decline of millennials voting among Democratic voters compared to 2012. In other words, it's not that all those people voted for Trump – they just didn't vote at all!
If we look at this from an entertainment-only perspective, then we can obviously see why someone would have chosen Trump: he was infinitely more entertaining than Hillary in the debates, even if his policy positions were deplorable. The retort makes a fair point that Trump's winning of the electoral college doesn't absolve his policies, but it doesn't necessarily mean that people voted for him solely because of policy either.
Ultimately, the fact remains that Trump did win in 2016 thanks to the electoral college system, and the answer to the original essay's question still stands: clearly a huge number of Americans really love the guy. Therefore, I think it's fair to conclude that "the more naturally funny candidate wins"– or at least has an advantage.
And if nothing else, we can learn one very important lesson from Trump's rise: if you want to win an election and become one of the most powerful people in the world, don't forget your comedy training. It could come in handy!