A-List Comedians Reveal Juicy Copywriting Techniques

David Lowenthal
4 min readApr 30, 2021

The other day, I was watching Jerry Seinfeld’s Netflix show, “Comedians in Cars Getting Coffee.”

If you haven’t seen it, the title pretty much sums up the premise of the show.

Each episode follows Jerry as he drives around with another famous comedian friend in a classic car going for coffee and talking about life and comedy.

While I was watching, I thought, “Man, there’s a TON of similarities between great comedy and great copywriting!”

Below are six insights from comedians that can help you write better sales copy and put more money in the bank:

1. Collect and Tell Stories: Great comedians are full of hilarious and engaging stories that keep their audience on the edge of their seats in preparation for the big laugh line.

And those stories are usually about an annoying or bizarre person we all know or meet regularly in our own lives.

As a copywriter, you should always be on the lookout for stories your prospect can identify with that relate to your product or service.

2. Creative Repetition: Another specialty of comedians is being able to always put fresh and new “spins” on everyday problems.

Example: You’d think by now people would be sick of jokes about airplane travel, the differences between men and women, and the entire state of New Jersey, wouldn’t you?

Nope.

Those jokes are as fresh as ever thanks to clever comedians.

The reason being that there are some problems, situations, and issues that audiences will NEVER get tired of.

So it is with comedy, so it is with a copy!

Your prospect is hungry (famished even!) to listen to someone talking about their problems.

It’s up to you as a copywriter to put a fresh new spin on old problems; for example, being overweight or investing with shady stock brokers.

3. Building Anticipation Through Emotion: If you want to witness a masterclass in dramatic anticipation build-up, watch the comedy special “Equanimity & The Bird Revelation” from Dave Chappelle — the world’s greatest living comedian.

In the special, Chappelle sets a random phrase as a punchline at the beginning and then tells the audience that he will use the punchline by the end of the show as a grand finale.

Successful copy works much the same way.

In the opening paragraph of a sales letter, you make your prospect a big promise they’ll get by reading your letter.

Then you pivot to building up anticipation to your big promise throughout your letter — typically through agitating your prospect’s problem and “future-pacing” how wonderful their life will be with your product.

4. Dramatically Demonstrate Your USP: There’s a scene in Jerry’s show where he’s in a coffee shop, sitting across from comedian Bill Maher which demonstrates this point perfectly.

The two are arguing about whether or not you should refer to waiters by name.

Jerry says “yes” because that way, if you know the waiter’s name, you can ask him/her to do little favors without coming off rude.

And sure enough: when they get up to leave, Jerry hands the waiter his napkin and the guy takes it — no questions asked.

Bill Maher is stunned and can’t understand why the guy complied.

But Jerry just replies:

“THAT’s why I got his name at the beginning. I told you, I was going to be needing him to do certain things!”

It’s a funny scene, and it gets Bill believing him by the end of it.

Lesson: Perform the “dramatic demonstration” of your product successfully in your copy and you will have ramped up your credibility 1000% with your prospect — and will have made a sale that much more likely!

5. Strike a Chord Through Strategic Controversy: Nobody likes a “yes man” or “people pleaser” who refuses to take any firm positions on anything.

Comedians gain loyal fans in part by stoking controversy and calling out stupidity.

Naturally, this makes the morality police quite upset.

But who cares?

As the late great A-list copywriter Gary Halbert (creator of the world’s most mailed sales letter in history) used to say:

Don’t worry about offending the “dogs.” Focus on selling to the “foxes”!

Which perfectly tees up the final copywriting lesson from comedians:

6. Positioning Yourself in Your Ideal Market: Different types of comedy hold different “market shares.” And with each year, comes more and more differentiated comedy for more and more segmented markets.

There’s black comedy, Jewish comedy, redneck comedy, hipster comedy, political comedy, offensive comedy, angry comedy, prop comedy, observational comedy, impression comedy, nerdy comedy, clean comedy, etc., etc., etc.

Great comedians know early on that they’re not everybody’s “cup of tea.”

Instead, they focus on building audiences and fan bases around their type of comedy so they can be a “big fish in a small pond.”

I’m sure there are many more juicy lessons that can be learned from comedians but these are the biggest ones that shot out at me.

David Lowenthal is an independent direct response fundraising serving libertarian and other freedom-loving nonprofits.

This chapter is part of his book 32 Jackpot Marketing Secrets from History’s Greatest and Craziest Persuaders! If you would like to discover more marketing secrets from some of history’s most successful entrepreneurs, copywriters, politicians, negotiators, lawyers, talk show hosts, actor/directors, political activists, and much more, you can download a copy of his FREE ebook, 32 Jackpot Marketing Secrets from History’s Greatest and Craziest Persuaders!, by signing up here.

After you sign up, you will also receive access to his free email newsletter, the David Lowenthal Report, giving you daily marketing secrets for copywriters who want to write breakthrough sales & fundraising copy for fun, profit & principle!

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David Lowenthal

Direct response fundraising copywriter for libertarian and pro-freedom nonprofit organizations