Writing about the news can be a depressing business. While events in Trump’s America are better than I ever imagined they could be, what’s happening around the world can be very unnerving, as we see liberal democracy blink out in one country after another. Moreover, given that I am Jewish, the rise of rabid, worldwide antisemitism, which is converging around destroying, not just Israel, but Jews generally, is not happy stuff.
And of course, watching Democrats’ antics is always worrisome because even when they’re down, they’re never out. They’re just waiting for further opportunities to destroy the constitutional, liberty-based, Judeo-Christian, Enlightenment American experiment.
Because the news can drag one down, that makes it even more important to cherish laughter when it comes our way. And here’s a real stunner: This time, the laughter came from John Oliver. I never thought I’d laugh at anything John Oliver has to say. However, when it comes to the fact that Sen. Chuck Schumer (D-NY) and his imaginary friends, Oliver hit it out of the park.
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For those fortunate enough never to have watched him, Oliver is an upper-middle-class, Cambridge-educated leftist from England. He got his start on John Stewart’s “Daily Show,” before being rewarded with his own HBO Show, “Last Week Tonight.”
For many years, I had a leftist friend who relentlessly sent me videos of Oliver’s monologues, assuring me that Oliver’s wit and erudition would convince me that my conservative views were just wrong. I did not find Oliver persuasive.
And, given that he’s supposed to be a comedian, I felt Oliver committed the ultimate sin: He was not funny. Instead, he made obvious leftist points to the trained seals in the audience, usually backed by labored analogies. Both wit and a comic sensibility were singularly lacking.
But sometimes, even an unfunny comedian, when given just the right material, can actually be funny—and believe it or not, the right material is Schumer. You see, it turns out that, for his entire political career, Schumer has explained to the world that his policies are geared toward the happiness of Joe and Eileen Bailey of Long Island, New York. They are the quintessential middle Americans, with “everyman” values (which, naturally enough, hew left), and Schumer’s made it clear that it’s his job to keep them happy.
The only problem with the Baileys is that they’re figments of Schumer’s imagination. That’s funny enough, but Oliver (or, more accurately, his writers) actually made it funnier, offering genuine comedic material. The only time the humor collapses is at the very end when Oliver is unable to resist turning Schumer’s madness into a mini-polemic advancing Oliver’s own political views.
So, this is probably the only time in my life that I will urge you to watch a John Oliver monologue. I’m doing so because (a) it reveals how detached from reality the Democrat political class is (I mean, literally detached from reality) and (b) it’ll make you laugh:
This is insane.
— Blue Georgia (@BlueATLGeorgia) August 11, 2025
Apparently, Chuck Schumer has based his entire political strategy on an entirely fictional Long Island couple named Joe and Eileen Bailey. pic.twitter.com/9NoQZMY2sZ