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The Gaze Mail · Apr 15, 2026

😏 The smuggest face in art

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Matthijs Van Mierlo · The Gaze Mail

If paintings could move, this man’s eyebrows would be bouncing up and down. He’s clearly enjoying himself, wearing a slightly arrogant, self-satisfied smirk. He looks as if he just folded his entire laundry without having any leftover socks. Which, in fact, would be an acceptable excuse for carrying such a smug face. Bravo.

However, despite the smugness, he does look fabulous. Just look at that perfectly trimmed grey beard, his broad neck and the pouted underlip. Or his rosy cheeks and slightly squinting green eyes. And topping it all off is his wild grey hair, serving as a cushion for a royal crown of laurels. Sure, this man looks way too pleased with himself, but honestly: he’s earned it, because he’s been through some crazy stuff.

Henry IV as Hercules slaying the Lernaean Hydra - Circle of Toussaint Dubreuil (c. 1600). Musée du Louvre, Paris. Oil on canvas, 36 x 29 in (91 x 74 cm)

There are two ways of looking at this painting, and the first one involves some insane mythology. Maybe you’ve heard of Hercules, the mythological hero who was tasked with completing 12 impossibly difficult labors. Folding a monumental mountain of laundry without ending up with leftover socks could’ve been one of them, but in reality they were slightly less mundane.

Take killing a nine-headed serpentine monster, for example, depicted here. It wasn’t a simple chore, because every time Hercules chopped off one of the monster’s heads, two new ones grew back. Luckily, Hercules called on the help of his nephew Iolaus, and his problem-solving abilities managed to save the day. “Maybe”, Iolaus suggested, “we should scorch the neck-stumps to prevent the heads from growing back”. The plan worked like a charm. Together they slayed the monster and Hercules could go back to shaving his insanely beautiful legs.

Those monsters are no match for those divine legs.

So that’s the mythology behind the portrait, but the smug face in this stunning painting doesn’t belong to Hercules, it belongs to Henry IV of France. And his proverbial nine-headed sea monster was called the French Wars of Religion. You see, Henry was a Protestant, which made him pretty unpopular with French Catholics. They didn’t want him as king, so they fought long and hard to stop him. During his lifetime, Henry survived at least 12 assassination attempts.

Henry IV of France - Wikipedia
Henry IV of France by Frans Pourbus the Younger (1609)

Despite all the anger pointed against him, Henry remained a pragmatic guy. Because to secure his throne, he decided to convert to Catholicism, supposedly saying “Paris is well worth a mass”. Five years after his conversion, in 1598, he also signed the Edict of Nantes, which guaranteed religious freedoms to Protestants. In doing so, cheeky Henry managed to balance the interests of both Catholics and Protestants. The result? The French Wars of Religion finally came to an end, which is well worth a glorious portrait.

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Engraving of cheeky Henry by H. Jacobsen (1614)

However, the painting got a bit ahead of itself, because in 1610, some ten years after it was painted, Henry finally met his end. He wasn’t killed by a nine-headed sea-monster, but by a dissatisfied Catholic zealot. He stabbed him to death, wiping that smug smile off Henry’s face for good. Lucky for us, we still have the painting.

Assassination of Henry IV, engraving by Gaspar Bouttats
The assassination of Henry IV (on the left), by Gaspar Bouttats (late 17th century)

The story you just read is just one of 50 you’ll find in my freshly released book Stupid Faces in Stunning Paintings. It’s OUT NOW (yay!) and available in major bookstores.

❤️ I’ve been getting some wonderful comments and DMs from readers. The ones that really make my heart jump are from parents telling me their kids snatched the book and started reading it before they could.

THAT. IS. THE. BEST.

I spent a perfect week of gazing at art in New York and Boston. I did a tour of eight museums, hunting for stories for new videos and for this newsletters. I found more than I can carry. 😊 Anyway, the trip required a photo dump:

This was the April issue of The Gaze Mail. Thanks for gazing and see you in May! ❤️

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