Funny How: Letters to a Young Comedian

Funny How: Letters to a Young Comedian

What's the joke here?

The standup special that made me mad at the crowd, not the comedian.

Matt Ruby's avatar
Matt Ruby
Jan 14, 2026
∙ Paid

An arena cheers on a charismatic man because of his captivating verbal skills and their fond memories of his hit TV show from the mid-2000’s.

Incredibly, he’s somehow both a victim and the hero in every story.

They overlook his slippage, cruelty, and narcissism because, to them, he has become a cult leader who can do no wrong.

After all, he insists he’s the greatest and the only one who can talk this way. They buy it.

They even applaud his PR shilling for the brutal Saudi regime because, y’know, other places do bad stuff too. (Plus, the Saudis pay him millions so they must be okay).

He mocks snowflakes, attacks the woke mob, and never misses a chance to take a shot at trans people. There are also long tangents into bizarre anecdotes that no one seems to quite comprehend.

Even if none of it makes any sense, they still loooooove it.

So here’s my question: Am I talking about Dave Chappelle or Donald Trump?

Comedian Dave Chappelle defends his past Trump remarks in new interview |  Fox News

Because after watching Dave’s latest special, I can’t stop thinking about how much their audiences behave similarly. In fact, The Unstoppable... made me feel something I’ve never felt while watching standup before…

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