10: Comedy Writing Tips with David Wolinsky

comedy writing tips
David Wolinsky, comedy writer, creator, and the teacher of my Humor Writing For The Internet classes at Second City, joins The Rob Cressy Show to talk about creating and comedy writing tips. How to stand out as a comedy creator, the balance between creating and pitching, being a disciplined creative, plus advice for those creators just starting out or who are already chasing the dream.

One quote from our conversation that really stood out to me was: “Nothing great ever came out of someones comfort zone.”

As someone who has studied improv and comedy writing at Second City for the last four years I can’t recommend their programs enough. Without a doubt they’ve helped me think better, be more successful at business and building relationships, plus enjoy myself for hours on end. Check out the classes that Second City Chicago offers and when you sign up for a class drop me a line and let me know.



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  • Check out previous episodes of The Rob Cressy Show here.


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1. Learning at Second City and the Power of YES AND – One of the comedic fundamentals and building blocks for improv. The power of YES AND has a way of completely transforming your outlook on comedy and life.

2. 11 Funny Filters to Write Jokes – Every joke created uses at least one of these 11 funny filters. When writing comedy use these funny filters and you’ll quickly see improvement in your jokes. These come straight from my Writing for The Onion class and Scott Dikkers.

3. 21 Comedy Writing Tips – These comedy principals are building blocks for the rest of your comedy writing and no doubt will help increase the quality of your jokes and writing. These also come straight from my Writing for The Onion class.

4. Follow Rob Cressy on Snapchat – If you are on Snapchat then you need to be following me faster than Antonio Brown can take one to the house. You can also check out my Snapchat For Business tips.

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5. Monday Morning Newsletter Get rid of your case of the Monday’s with Rob Cressy’s weekly Monday Morning newsletter. It’ll give some extra motivation and inspiration to those who strive to do great things.

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Comedy  //  Content  //  creativity  //  Writing


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Cress Media is a Chicago Sports Marketing Content Studio. We help brands activate sports fans by telling their story in a fun and engaging way via audio, video, and social content creation. We get your audience talking, taking action, and having fun with your brand online and offline. Whether in Chicago or any other part of the country Cress Media can handle your content creation and sports marketing needs.