The Indian transport ministry is experimenting with 3D paintings on highways to make motorists slow down. Kelly Grovier looks at the history of artworks that confuse our eyes.

Does painting still have the power to stop us in our tracks, let alone save our lives? India’s transport ministry is counting on it. Photos floating through social media this week have delighted in the experimental use of optical tricks in the painting of crosswalks in India. From the point of view of drivers approaching these pedestrian crossings, the flat white zebra stripes that our eyes are accustomed to seeing suddenly appear to levitate like weightless rafters in space.

By mesmerising motorists with the arresting 3D technique, civic planners are hoping to reduce the number of accidents caused by speeding. In doing so, they have tapped into an intriguing artistic tradition and, in particular, the power of a 16th Century masterpiece that was likewise conceived at the intersection of optical illusion and mortal salvation.

When it was unveiled in 1533, the double portrait The Ambassadors by the German and Swiss artist Hans Holbein the Younger must have struck observers as a road-bump for the soul. Looked at straight-on from the front, the huge oil-on-oak painting is enigmatic enough, presenting to the observer a pair of distinguished diplomats caught in a clutter of worldly amusements: musical instruments and scientific whatnots scattered about the shelves on which they lean.

But pass by the painting at a shallow angle from the left, such that your eye catches the work by chance in the periphery of its vision, and a mystery tucked into the centre of the painting stops you cold. Only from that askance vantage do you see the optical illusion Holbein has secretly positioned into the foreground of his work: the cracked cranium of a spooky skull grinning back you. Holbein’s twisted skull is a version of the traditional artistic device of the momento mori (or “remember you must die”), used by painters and sculptors to elevate their works into spiritually teachable moments that remind observers that this world is transitory and that they must live virtuously and seek salvation.

Perhaps concerned that observers had become too accustomed to seeing skulls in Medieval paintings and that their religious impact had become fatigued, Holbein appears to have upped the ante on the memento mori by transforming the device into a macabre surprise that jumps out from the shadows. Like the 3D stripes in the crosswalks in India, the skull is an example of artistic “anamorphosis”. It’s just an illegible blur when seen from any other angle than the surprising one from which Holbein hopes he’ll trip you up.

Once seen for what it is, the skull overshadows the worldly significance of the symbols of cultural refinement that surround Jean de Dinteville, the French ambassador to London (on the left), and his companion, the papal diplomat Georges de Selve, the Bishop of Lavaur (on the right). In the distended light of Holbein’s elastic skull, the soul slams on its brakes and yields to the path that leads from this world to the next.

100 Works of Art That Will Define Our Age by Kelly Grovier is published by Thames & Hudson.

If you would like to comment on this story or anything else you have seen on BBC Culture, head over to our Facebook page or message us on Twitter.

And if you liked this story, sign up for the weekly bbc.com features newsletter, called “If You Only Read 6 Things This Week”. A handpicked selection of stories from BBC Future, Earth, Culture, Capital, Travel and Autos, delivered to your inbox every Friday.