Funny How: Letters to a Young Comedian
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How to massage an extremely dark joke
Advice from Mike Birbiglia on finding comedy in difficult topics.
Jul 11
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Matt Ruby
4
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Funny How: Letters to a Young Comedian
How to massage an extremely dark joke
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23 ways to attack a joke premise
Good ideas for getting from setup to punchline.
Jul 9
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Matt Ruby
4
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Funny How: Letters to a Young Comedian
23 ways to attack a joke premise
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What Woody Allen’s manager told him that changed his standup
On laughs vs. smiles.
Jul 7
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Matt Ruby
3
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Funny How: Letters to a Young Comedian
What Woody Allen’s manager told him that changed his standup
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Bill Burr’s answer to “Can women be funny?”
Some wise advice on how to approach standup.
Jul 2
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Matt Ruby
1
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Funny How: Letters to a Young Comedian
Bill Burr’s answer to “Can women be funny?”
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June 2025
Larry Charles on the only genuine emotion that fuels comedy
The comedy guru explains why hugging and learning are anathema to comedy.
Jun 30
•
Matt Ruby
4
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Funny How: Letters to a Young Comedian
Larry Charles on the only genuine emotion that fuels comedy
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3
Brian Regan on the most difficult thing about standup
Plus other great quotes from Robin Williams, Gilbert Gottfried, Bill Burr, and Chris Rock.
Jun 27
•
Matt Ruby
3
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Funny How: Letters to a Young Comedian
Brian Regan on the most difficult thing about standup
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On shock therapy, righteous indignation, and why comedy's so lonely
Highlights from "Comedy Book: How Comedy Conquered Culture—and the Magic That Makes It Work" by Jesse David Fox.
Jun 25
•
Matt Ruby
6
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Funny How: Letters to a Young Comedian
On shock therapy, righteous indignation, and why comedy's so lonely
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4
Key and Peele: Make fun of everything
"To not make fun of something is, we believe, itself a form of bullying."
Jun 23
•
Matt Ruby
1
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Funny How: Letters to a Young Comedian
Key and Peele: Make fun of everything
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Tension is an opportunity
A little audience discomfort is a good thing. Plus, thoughts from Bill Burr and George Carlin on crossing the line.
Jun 20
•
Matt Ruby
3
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Funny How: Letters to a Young Comedian
Tension is an opportunity
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0:54
The real problem with calling "The Bear" a comedy
And what Fleabag, Atlanta, and Louie all had in common.
Jun 18
•
Matt Ruby
4
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Funny How: Letters to a Young Comedian
The real problem with calling "The Bear" a comedy
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A podcast on PR and branding in comedy
Jason Zinoman, NY Times comedy critic, guested it up on Sean Murphy’s Some Things Considered podcast.
Jun 16
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Matt Ruby
1
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Funny How: Letters to a Young Comedian
A podcast on PR and branding in comedy
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The worst sin you can commit as a comedian
A deep dive interview with me about comedy, algorithms, meditation, tension, and more.
Jun 13
•
Matt Ruby
8
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Funny How: Letters to a Young Comedian
The worst sin you can commit as a comedian
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