I get in arguments with folks about Jon Stewart occasionally and think I may be the only person with a sinister view of his career. Were in not for The Daily Show, he would be grinding on the road doing club dates to audiences of 200-300 people. He was a stand-up comedian who parlayed "G.W. Bush is dumb" into an 8-figure salary. Making fun of Republicans was simply a tag line for him and he hammered it, every night, making "owning" Republicans and feeling smug sort of enough for most rank-and-file Democrats in the process:

"I'm informed, I get my news from The Daily Show," was something of a buzz point for many years when he was on air.

People have attributed the populist Trump wave to a number of things, but I really think Stewart contributed as much to it as anyone, by elevating the culture wars, between like rural and urban in particular, with his brand of snark. All the while he was cashing BIG checks (he was making ~$25 million/year by the time that show went off the air).

I suspect I agree with him on most points (and what he's doing here def seems genuine and bold) and think he's a deft and skilled comedian and presenter, but I think professionally he has more in common with the likes of Rush Limbaugh than just about anyone else.