These 25 Ad Headlines from 60+ Years Ago Work Just as Well Today

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Inspired by How to Write a Good Advertisement

Every now and then, I’ll pick up How to Write a Good Advertisement: A Short Course in Copywriting by Victor O. Schwab and skip around for inspiration. It never fails to get me thinking about marketing and copywriting with a fresh perspective. Drawing on 44 years as a copywriter (from 1917 to 1961), Schwab shares timeless insights about the fundamentals of good copy, the psychology behind great ads, and the numerous techniques that can be combined to turn prospects into customers.

One of the sections in the book is a section called “100 Good Headlines and Why They Were so Profitable.” What’s striking about this list is that so many of them are relevant and directly applicable today. Some of these headlines were probably written over 100 years ago, and despite all the technological advances in society, human nature has remained the same.

I revisited the 100 headlines and cherrypicked 25 that I felt could be useful in my own work and potentially helpful to others who need to write headlines. Whether it’s for ads, blog posts, tweets, marketing websites, YouTube videos, Instagram captions, or anywhere else, modern life is filled with instances where we’re prompted to craft headlines. Once you spot certain patterns and structures, it’s hard not to see them everywhere.

1. A little mistake that cost a farmer $3,000

“People will fight much harder to avoid losing something they already own than to gain something of greater value that they do not own”

Playing up our loss aversion bias, this headline compels the reader to find out what this “little mistake” may be and what remedies exist. I often see this type of headline from business-to-business (B2B) vendors who promise they can help save large amounts on things like IT, taxes, and administrative expenses.

2. Advice to wives whose husbands don’t save money–by a wife

While the husband/wife labels feel dated and probably won’t get much play today, the structure of this headline has some really great attributes. The headline is targeting wives and also assuring them that the advice is coming from someone relatable–there is “insider” information and it addresses a serious problem (husband not saving money).

  • Advice to founders whose investors aren’t helpful–by a founder
  • Advice to parents whose kids don’t behave–by a parent
  • Advice to landlords whose tenants don’t pay–by a landlord
  • Advice to product managers whose engineers are struggling–by a PM
  • Advice to marketers whose clients won’t listen–by a marketer

This headline can be a serious generator for some click-baity content. I’m sure you’ve seen variations of this in many places.

3. Are you ever tongue-tied at a party?

A headline like this hits at the insecurity of the reader and captures their attention–perhaps there’s a solution to being tongue-tied if they read on?

The “Are you ever [specific problem]?” is simple and elegant. It can keep hitting at insecurities (“Are you ever self-conscious about the way your clothes fit?”), be about a particular state of mind (“Are you ever feeling overwhelmed by all your responsibilities?”), or be about a certain situation (“Are you ever frustrated by long lines at the doctor’s office?”).

4. How a new discovery made a plain girl beautiful

“Wide appeal: there are more plain girls than beautiful ones–and just about all of them want to be better looking.”

This type of language specifically around looks may be rejected today as it runs counter to the culturally-accepted idea that “everyone is beautiful in their own way”, but the idea of “plain” turned into something better can still be effective. I can imagine something like “How a new discovery made a couch potato into an endurance athlete” or “How a new discovery made a hypochondriac fearless”.

5. Do you make these mistakes in English?

This headline is “a direct challenge” that forces the reader to ask themselves “What mistakes? Do I make them?”

I absolutely love this headline because you can make it be just about anything and then pull readers to learn more, perhaps sign up for something, and ultimately even pay up for a product or service. Examples that come to mind are:

  • Do you make these mistakes in managing your time?
  • Do you make these mistakes when using email?
  • Do you make these mistakes in leading your team?
  • Do you make these mistakes in the kitchen?
  • Do you make these mistakes with your partner?
  • Do you make these mistakes with your kids?
  • Do you make these mistakes with your money?

6. You can laugh at money worries–if you follow this simple plan

It’s hard to beat a headline that offers the promise of eliminating money worries, but the overall structure is also very appealing. I can see the idea of “laughing at X worries… if you follow this simple plan” having some legs when it comes to other anxiety-inducing situations.

  • You can laugh at weight gain worries–if you follow this simple plan
  • You can laugh at parenting worries–if you follow this simple plan
  • You can laugh at relationship worries–if you follow this simple plan
  • You can laugh at promotion worries–if you follow this simple plan

The allure of a “simple plan” is irresistible, especially if the problem seems especially hard.

7. Why some people almost always make money in the stock market

Schwab points out “some” and “almost” as words that make this headline extra credible. It points to knowledge or a secret that these select “some people” possess and makes the reader more curious. I like seeing different applications of this played out:

  • Why some people almost always have high energy levels
  • Why some people almost always win their business deals
  • Why some people almost always inspire their employees
  • Why some people almost always maintain a tidy household
  • Why some people almost always have time to do everything they want

8. Five familiar skin troubles–which do you want to overcome?

Having worked with beauty brands over the years, I know for a fact that these types of headlines are powerful if paired with compelling and credible content. It’s easy to imagine a funnel shape up with this headline: you see a TikTok post or an Instagram ad that starts with this headline followed by 5 quick facts told in fast-pace video format with a call-to-action (CTA) that leads to a landing page where you can sign up by email or purchase the product right there. If you leave your email, you’ll likely get some follow-up emails that reprise the five familiar skin troubles, perhaps with greater depth, and each of those emails will have CTAs that lead to a landing page where you can buy the product.

9. Which of these $2.50-to-$5 best sellers do you want–for only $1 each?

This is an incredibly strong bargain pull and catnip for deal-hunter types. I can imagine a website selling wines or clothing doing this: “Which of these $25-to-$30 cabs do you want–for only $15 each?” or “Which of these $150-to-$175 cashmere sweaters do you want–for only $100 each?”

10. How I improved my memory in one evening

You may categorize this type of headline as “user generated content” (UGC) in today’s terminology. Taking a customer’s review or testimonial about a service or product experience and making it a headline is an impactful way to leverage social proof. Even better if there are specifics like the impact (“improved my memory”) and the timing (“in one evening”).

  • How I improved my sleep in 21 days
  • How I gained 10 pounds of muscle in 1 month
  • How I landed a new job in 2 weeks

11. Discover the fortune that lies hidden in your salary

Something valuable that’s “hidden” in plain sight is sure to grab a reader’s attention. This headline structure can also be used to play up the idea of something great coming out of something mundane. These are some examples that came to mind:

  • Discover the Michelin-starred meals that your home kitchen can turn out
  • Discover the key to endless energy that lies hidden in your morning routine
  • Discover the life-changing relationships that lie hidden in your LinkedIn account
  • Discover the time-saving shortcuts that lie hidden in Gmail

12. How often do you hear yourself saying: “no, I haven’t read it; I’ve been meaning to!”

Schwab mentions that this headline worked very well for a book club business. The structure of this headline lends itself to any product or service that promises self-improvement and personal development while also promising convenience and quick results. It plays upon our guilt of lacking discipline.

  • How often do you hear yourself saying: “no, I haven’t exercised; I’ve been meaning to!”
  • How often do you hear yourself saying: “no, I haven’t cooked; I’ve been meaning to!”
  • How often do you hear yourself saying: “no, I haven’t prioritized sleep; I’ve been meaning to!”
  • How often do you hear yourself saying: “no, I haven’t called my parents; I’ve been meaning to!”

13. Guaranteed to go thru ice, mud, or snow–or we pay the tow!

If you’re confident that your product can back up the claims, a guarantee can be a powerful message to play up to prospective customers. Schwab’s point was that if a business is already offering some kind of a guarantee, make it a big part of the advertising message.

14. Profits that lie hidden in your farm

In the same vein as “Discover the fortune that lies hidden in your salary”, this headline is about finding opportunities right in front of you. I see this especially from companies that promise businesses that they can find creative ways to reduce taxes or use sophisticated software to identify cost savings. Such claims are hard to pass up since nobody wants to leave money on the table.

15. Six types of investors–which group are YOU in

Today, this type of headline can be tied to quizzes or assessments that then lead to a recommended product or services offering. People also can’t resist the pull of knowing what “type” they fall into, and if done well, people will gladly share their results with friends, making the quiz/assessment go viral. This was an important part of what helped Buzzfeed grow their audience in the early days and we also see the draw through the popularity of astrology content and personality tests.

16. Does YOUR child ever embarrass you?

Written as a fairly aggressive-sounding question, this headline instantly triggers bad memories in the target audience and draws them into learning more about a proposed solution. It’s a negative headline but one that can be effectively deployed to grab attention and nudge action. The word “embarrass” is also quite powerful here. Some explorations came to mind for me:

  • Does YOUR cooking skills embarrass you?
  • Does YOUR posture embarrass you?
  • Does YOUR spending ever worry you?
  • Does YOUR job ever stress you out?

17. The crimes we commit against our stomachs

There’s a degree of hyperbole in this headline with the use of the word “crime”, which helps it stand out. Instantly, the reader is left asking themself, “What crimes? Should I not be doing something? Am I eating too much garbage?” Those who are already guilty about their diets may feel anxiously curious while those who are confident in their diets may want to read on to confirm what they already know and feel good about it. Either way, the headline is attention-grabbing and a possibly effective lead-in for useful content plus a relevant solution.

My takeaway here was in the use of a pointy word like “crimes” paired with the “we” to make it something terrible that afflicting all or many of us. Some alternatives that came to mind:

  • The torture we put our face through everyday
  • The horrific form that’s hurting our golf game
  • The annoyances we put up with during tax season

18. FREE BOOK–tells you 12 secrets of better lawn care

This headline may have been for a free booklet back in the day, but today, it can easily be substituted for an e-book / PDF download that requires an email sign-up. The promise of compelling knowledge for free is an effective way to grow one’s email list and follow up with nurture campaigns. I can actually think of a client who might benefit from using this very headline!

19. How much is “worker tension” costing your company?

This particular headline is great for targeting company executives and getting them to wonder about their own problems. “Worker tension” may not be a term we use much today, but it’s easy to think of some alternatives:

  • How much is “Zoom fatigue” costing your company?
  • How much is “software overload” costing your company?
  • How much are endless meetings costing your company?
  • How much are useless performance reviews costing your company?
  • How much is multitasking costing your company?

20. New cake-improver gets you compliments galore!

Schwab shares a concept called BOY PT MOM or “Because of You, People Think More Of Me”, where you are selling the impact of the product on the customer’s reputation. Basically, the pitch boils down to: “we’ll make you look good”, which to this day is still a compelling reason to buy something and it sometimes works when you state it explicitly.

I don’t love how this type of headline sounds and it feels a bit stilted when I explore other examples, but then again, they might actually work just fine when you test them out on ads, especially TV infomercials where such statements seem to be widely accepted:

  • New grill that will impress your buddies
  • New pizza oven that’ll be the talk of the evening
  • New electric vehicle that’ll turn your neighbor’s heads

21. Great new discovery kills kitchen odors quick!–makes indoor air “country-fresh”

“Faces a common problem head-on; offers an easy and pleasant solution.”

This straightforward format of “great new discovery [does this] quick – makes [desirable outcome]” can be a great way to introduce a new product that is more effective than what exists out there today. I can still imagine a brand like Febreeze using this headline to get across its core value proposition. Here are some of my explorations using the structure:

  • Great new discovery speeds up website builds!–no more long and expensive projects!
  • Great new service makes home selling lighting fast–close a deal in under 2 weeks
  • Great new discovery charges your phone quick!–makes “low battery” a thing of the past

22. Suppose this happened on YOUR wedding day!

This anxiety-inducing headline is laced with some schadenfreude, playing upon our tendency to find pleasure in reading about the misfortune of others. The headline draws the reader to learn more and then to contemplate whether or not what happens in the story is something to worry about. The greater the worry, the more compelling whatever the offer or solution may be.

I can think of so many applications for this, either as a specific “big day” or a more general situation (change the “on” to “in” , “at”, or “to”).

  • Suppose this happened on YOUR kid’s first day of school!
  • Suppose this happened on YOUR big presentation day!
  • Suppose this happened on YOUR website launch day!
  • Suppose this happened at YOUR company!
  • Suppose this happened in YOUR marriage!
  • Suppose this happened to YOUR metabolic system!

23. Are they being promoted right over your head?

This headline gets right to an insecurity that many workers can identify with right away: are others getting ahead of me, and what’s keeping me from being advanced in my career?

This headline is a great lead-in to meaty content that can then drive to some kind of sign-up or purchase. Even someone confident in their position and career prospects may still pause at this headline just to check and see if there’s information that may be helpful.

The use of the word “they” is so powerful here–it allows the reader to project whomever they see as a threat or competition.

Some variations of this that come to mind for me are:

  • Are they winning deals that you’re unable to close?
  • Are they much closer to financial freedom than you are?
  • Are they getting work done in half the time it takes you?

24. FORMER BARBER EARNS $8,000 in 4 months as a real estate specialist

Stick around social media long enough and this type of headline will inevitably pop up. The “get rich quick” headline is irresistible for even the smartest people out there. Where there is speculation and easy money to be made, there will be headlines like “19-YEAR OLD MAKES $1.2 million selling NFTs”, “UNEMPLOYED COUPLE EARNS $400,000 per month with dropship ecommerce”, or “29-YEAR OLD TEACHER CASHES IN $575k trading stocks”.

These headlines typically lead to some kind of course where the buyer can “learn the secrets” to make money fast. But I do think there are legitimate ways to use this structure in productive ways. It’s about transformation and concrete results, which is why such headlines are so effective.

  • Traditional web design agency earns $1 million in 6 months after productizing their services
  • Retired athlete generates $10 million in annual cashflow with franchise businesses
  • Former marketing employee earns $300k per year as YouTube star

25. ONE PLACE-SETTING FREE for every three you buy!

You can never underestimate the power of a good deal and how attuned humans are to spotting something that feels like a bargain. In addition to the one above (a variation of a Buy One, Get One, or BOGO), Schwab shares a couple more.

  • Save 20 cents on 2 cans of cranberry sauce–limited time offer
  • Take any 3 of these kitchen appliances–for only $8.95 (values up to $15.45)

Not all brands and products are fit for these types of deal-focused headlines, and it’s a delicate balance to not over-do these types of promotions. But when used appropriately and executed well, these headlines really do drive enormous traffic and conversions, just like they probably did via newspapers and flyers 60+ years ago.


Great headlines capture a reader’s attention and capturing a reader’s attention is all about standing out and making them feel something. And we are most likely to feel something strongly when it’s about ourselves. We are, as individuals, our own and most important topic. Anything that makes us think about ourselves is more likely to create pause and stir interest.

Drawing on these headlines and some lessons from Schwab’s book, I’ve listed some questions to help spark headline ideas. The list reads like the insecurities of a neurotic person, but it’s hard to argue that we all don’t consciously or subconsciously care about all or some of these things on a daily basis.

  • What am I insecure about?
  • What am I afraid of?
  • How can I look good?
  • How can I get ahead?
  • How can I be better than [someone else]?
  • How can I feel secure?
  • How can I feel safe?
  • How can I feel comfortable?
  • How can I feel confident?
  • How can I feel fulfilled?
  • How can I save time/money/hassle?
  • How can I make it easy?
  • How can I make more money?
  • How can I get others to like me?

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