While it goes against the grain of pop culture, I have never found Stewart to be insightful or funny. Night in and night out, he panders to the same, worn out crowd who hates all things conservative. If he didn’t have 30 writers on staff, he would be about as funny as Dane Cook.
Why did the media miss Trump's continued success?... It's simple: the media are out of touch with Trump for the same reason they no longer relate to the majority of America -- they are cloistered and arrogant and agenda-ridden and can't get out of their own liberal bubble. From the WSJ to MSNBC, it's the same. You have basically resorted to covering each other. Trump speaks directly, and he's speaking the truth.