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Playfully Inappropriate: The Fun Way to Write Comedy
Why are some comedians so incredibly funny, yet feel so natural and authentic on stage, as if not even telling jokes?
This book breaks down the psychology behind that effortless humor and reveals the single system that every funny person uses to get laughs. If you master that system, you can be funny in any situation.
In Playfully Inappropriate, comedy trainer and comedian Jared Volle, an expert in the psychology of humor and creativity, offers a radically different approach to writing comedy that mirrors your natural sense of humor.
It ignores the highly structured, mechanical approach to writing and introduces a playful, intuitive system that aligns with how naturally funny people think and respond.
Psychology of Humor
Learn the one universal law behind all laughter, grounded in the latest humor research, and how it forms the foundation for being funny in every situation, on stage or off.
Comedic Storytelling
Discover how masters of comedic storytelling quickly capture the audience’s attention, build comedic tension, and release it through punchlines that sound natural and authentic. Explore examples from stand-up comedians like Brian Regan, John Mulaney, and Tom Segura, sketch shows like Key & Peele and Alternatino, and storytelling masters like Pixar.
Joke Writing
Learn how to apply one intuitive strategy across twenty different joke types, so you never have to memorize separate formulas. This flexible approach helps you write faster, generate stronger material, and stay true to your natural comedic voice.
In this guide, you will learn how
Turn personal experiences, opinions, and observations into funny jokes or comedic stories.Use a step-by-step writing process that taps into your natural, off-stage sense of humor.Build comedic tension in your setups that makes the audience think, “Oh, I like where this is going!”Create huge laughs without sounding awkward or jokey.Use the one universal law behind all laughter to create humor in any situation.
You will also find joke breakdowns from top comedians, with insights into what makes them both authentic and hilarious, and how to apply those techniques to your own comedy.
Whether you’re just starting out or refining your voice, Playfully Inappropriate gives you proven tools to sharpen your comedy writing, develop original material, and craft stories that are both hilarious and personal.
The second edition expands portions of the writing guide, simplifies ideas to make them easier to apply in stand-up, sketch comedy, and improvisational comedy, and features updated comedian quotes, material breakdowns, and walkthroughs.
If you want to write original material that feels like you and makes people laugh, this book will give you the system, tools, and confidence to make it happen.
“There’s no doubt that reading this book will improve your comedy and comedy writing to the point that it becomes a superpower.” - Comedypreneur.com
This book breaks down the psychology behind that effortless humor and reveals the single system that every funny person uses to get laughs. If you master that system, you can be funny in any situation.
In Playfully Inappropriate, comedy trainer and comedian Jared Volle, an expert in the psychology of humor and creativity, offers a radically different approach to writing comedy that mirrors your natural sense of humor.
It ignores the highly structured, mechanical approach to writing and introduces a playful, intuitive system that aligns with how naturally funny people think and respond.
Psychology of Humor
Learn the one universal law behind all laughter, grounded in the latest humor research, and how it forms the foundation for being funny in every situation, on stage or off.
Comedic Storytelling
Discover how masters of comedic storytelling quickly capture the audience’s attention, build comedic tension, and release it through punchlines that sound natural and authentic. Explore examples from stand-up comedians like Brian Regan, John Mulaney, and Tom Segura, sketch shows like Key & Peele and Alternatino, and storytelling masters like Pixar.
Joke Writing
Learn how to apply one intuitive strategy across twenty different joke types, so you never have to memorize separate formulas. This flexible approach helps you write faster, generate stronger material, and stay true to your natural comedic voice.
In this guide, you will learn how
Turn personal experiences, opinions, and observations into funny jokes or comedic stories.Use a step-by-step writing process that taps into your natural, off-stage sense of humor.Build comedic tension in your setups that makes the audience think, “Oh, I like where this is going!”Create huge laughs without sounding awkward or jokey.Use the one universal law behind all laughter to create humor in any situation.
You will also find joke breakdowns from top comedians, with insights into what makes them both authentic and hilarious, and how to apply those techniques to your own comedy.
Whether you’re just starting out or refining your voice, Playfully Inappropriate gives you proven tools to sharpen your comedy writing, develop original material, and craft stories that are both hilarious and personal.
The second edition expands portions of the writing guide, simplifies ideas to make them easier to apply in stand-up, sketch comedy, and improvisational comedy, and features updated comedian quotes, material breakdowns, and walkthroughs.
If you want to write original material that feels like you and makes people laugh, this book will give you the system, tools, and confidence to make it happen.
“There’s no doubt that reading this book will improve your comedy and comedy writing to the point that it becomes a superpower.” - Comedypreneur.com
237 pages, Kindle Edition
Published August 12, 2025
3 people are currently reading
1 person want to read
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Displaying 1 - 2 of 2 reviews
August 14, 2025
Graduate level comedy made simple and fun!
I found Jared on YouTube and the books back up what he teaches. It helps me ask the right questions so my material gets funnier and more personal. It's detailed without being confusing. The technical parts are there when I want them and not required to get results.
What I like about the book...*It guides you past basic setup and punch into real storytelling. *Clear steps smart exercises, and examples that made me laugh while illustrating the point. *Explains the why behind the comedy so I can fix jokes not just write more. *Works for beginners and working comedians. *You can read it in pieces and apply it the same day...
I'm a left-brained doer who wants to create right-brained work. I've read the usual list of Comedy books. Like the other ones this one also clicked however it gave me a new lens and a clean road map for today's style of stand-up. If you want to move on from just lines to compelling comedic stories, get "Playfully Inappropriate."
I found Jared on YouTube and the books back up what he teaches. It helps me ask the right questions so my material gets funnier and more personal. It's detailed without being confusing. The technical parts are there when I want them and not required to get results.
What I like about the book...*It guides you past basic setup and punch into real storytelling. *Clear steps smart exercises, and examples that made me laugh while illustrating the point. *Explains the why behind the comedy so I can fix jokes not just write more. *Works for beginners and working comedians. *You can read it in pieces and apply it the same day...
I'm a left-brained doer who wants to create right-brained work. I've read the usual list of Comedy books. Like the other ones this one also clicked however it gave me a new lens and a clean road map for today's style of stand-up. If you want to move on from just lines to compelling comedic stories, get "Playfully Inappropriate."
August 14, 2025
I read the first edition of this comedy-writing handbook several years ago and continue to be impressed with the author's deep dive into humor in this second edition. Performers and writers who want to study the finer points of what makes funny happen will benefit from this book.
Volle uses a conversational tone, but does not skimp on the science (Benign Violation Theory, anyone?). He includes dozens of funny examples to prove his points. Just as helpful are his bullet-point summaries at the end of each chapter. As the co-founder/co-host of a stand-up comedy open mic since 2008, I've seen hundreds of comedians and storytellers at every skill level. "Playfully Inappropriate" (and its companion workbook) has something for each of them. (And me!)
Thanks to the author for providing the advance reader copy.
Volle uses a conversational tone, but does not skimp on the science (Benign Violation Theory, anyone?). He includes dozens of funny examples to prove his points. Just as helpful are his bullet-point summaries at the end of each chapter. As the co-founder/co-host of a stand-up comedy open mic since 2008, I've seen hundreds of comedians and storytellers at every skill level. "Playfully Inappropriate" (and its companion workbook) has something for each of them. (And me!)
Thanks to the author for providing the advance reader copy.
Displaying 1 - 2 of 2 reviews