Funny How: Letters to a Young Comedian

Funny How: Letters to a Young Comedian

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Why South Park feels so punk rock
How Trey Parker and Matt Stone make satire that bites the billionaire hands that feed them.
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Matt Ruby
1
Is martyrdom the new key to making it in show biz?
Comparing Stephen Colbert to Shane Gillis.
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Matt Ruby
1
Why Jay Leno never shared his political opinions on The Tonight Show
"Why shoot for just half an audience all the time? You know, why not try to get the whole."
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Matt Ruby
1

July 2025

Should I abandon my political material in front of a MAGA crowd?
Lessons from a night on the road.
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Matt Ruby
Don’t make fun of Nickelback or Spirit Airlines
How to avoid "Millennial Snot."
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Matt Ruby
8 observations about standup on social media
On crowdwork clips, the algorithm, and more.
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Matt Ruby
7
On turning your life into art instead of just living it
Re: the Observers Paradox.
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Matt Ruby
Colbert and the slow death of dissent
A closer look at what really ended Colbert’s run — and what it says about comedy, corporations, and cowardice.
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Matt Ruby
How comedians should talk about politics
The value of living on the outside, looking in.
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Matt Ruby
How standup can make you a better person
A former comedian now sees his failure as "the best thing that ever happened to me."
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Matt Ruby
2
10 Good Things: The secret to getting viral clips, Larry Charles, Ali Wong, and psychics
Plus thoughts on justice, transgression, and how nobody really cares.
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Matt Ruby
How to massage an extremely dark joke
Advice from Mike Birbiglia on finding comedy in difficult topics.
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Matt Ruby
© 2025 Matt Ruby
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