The Fine Art of Crafting a Not-Quite-Clickbait Headline

Headlines are super important. Your blog post, LinkedIn article, YouTube video, press release, or webpage will get more attention when it includes a well-crafted headline. However, there is a fine line between a clickbait headline and one that delivers on its promise.

I’m currently reading When the Going Was Good: An Editor's Adventures During the Last Golden Age of Magazines by Graydon Carter, founder of Spy magazine and long-time editor of Vanity Fair. I was an avid reader of Vanity Fair during the Carter era and loved the magazine.

In his book, Carter talks about a lunch he had with Don Hewitt, who created the TV news program 60 Minutes for CBS and ran it for three decades. Hewitt told Carter that Vanity Fair headlines were lacking, pulling out the September 2005 issue.

Hewitt pointed to a story about a 1938 boxing match between Joe Lewis, a Black American and Max Schmeling, a German fighting on the eve of World War II. The Vanity Fair headline was “War of the Worlds”. Hewitt said that wasn’t catchy enough and suggested “How did a Fistfight in the Bronx Make the Front Pages of Every Newspaper in the World?” Carter admitted that was indeed catchier.

I’m okay at writing headlines, but not great. I struggle over what best describes what my article is about but also provides a bit of intrigue so more people might check it out.

Using AI to write headlines

Recently I’ve been heading over to one of the AI chatbots to help out. I drop my nearly completed article with a prompt asking it to suggest a compelling headline.

ChatGPT often suggests good headlines, but they frequently seem over the top, designed more for a tabloid newspaper. Therefore, I usually end up modifying one of those suggestions.

My placeholder headline for this article was “Your Headline Goes Here”. I knew it wasn’t great, but I like having something – anything – as a starting point.

I asked ChatGPT about a headline for this post. The one that I chose was adapted from a ChatGPT suggestion, “The Fine Art of the Not-Quite-Clickbait Headline”, which ChatGPT says “highlights your central theme with a wink”.

I just added “Crafting” to the ChatGPT suggestion.

Here are a few other headlines ChatGPT suggested for this article, together with the reasoning:

“Why Great Headlines Matter — And What 60 Minutes Taught Vanity Fair”

→ Taps into authority (60 Minutes, Vanity Fair) and creates intrigue.

“Good Writing Doesn’t Matter If Your Headline Doesn’t Work”

→ A little provocative, invites curiosity.

“What a TV Legend Taught a Magazine Icon About Headlines”

→ Teases the Don Hewitt–Graydon Carter anecdote.

“Your Headline Is More Important Than You Think—Just Ask Graydon Carter”

→ Adds a personal angle and namedrop appeal.

“From Vanity Fair to 60 Minutes: The Secret to a Headline That Hooks”

→ Implies an insider’s view on effective media strategy.

“Crafting Headlines That Work: Lessons from Editors Who Knew How to Sell a Story”

→ Classic and informative with historical weight.

“How One Boxing Match (and a Better Headline) Made History”

→ Anchored in your Joe Louis anecdote, this leads with story.

“Don’t Bury the Lead: Headlines That Actually Get Read”

→ Playful, direct, and actionable.

“When a Fistfight Beat a Magazine Headline—and What You Can Learn from It”

→ Echoes the anecdote, creating curiosity and contrast.

What about you? How do you craft headlines?