Great works: D'-JIA-VU? (The Stock Market)1937

The art of trompe l'oeil mystifies, amuses and beguiles in just about equal measure. Its very self-consciousness pushes the illusionism of painting to comic extremes. Some of the finest works of trompe l'oeil were produced by the Dutch in the 17th century. They were especially fond of showing us pendent game birds that looked ripe for plucking off the wall and plunging into the steaming pot.

The weirdly anachronistic masterpiece on this page is an oddity in all kinds of ways. Little is known about the artist other than that he was born in Dresden in about 1885, emigrated to the USA, trained as an engineer and, late in life, emigrated to East Germany at the height of the Cold War. His art was a private affair. He sold just two paintings during his lifetime. Otis Kaye was not in fact his real name. No one knows what that was. Kaye was obsessed by the subject of money, as many other American painters had been in the 19th century – the greenback had helped to give groundedness and cohesiveness to that relatively young nation – and this painting is a kind of mysterious autobiographical journey, a portrait of one man's financial pain.

And yet, looked at in another way, it is not mysterious at all. It is perfectly evident what the sum of its parts consists in – dollar bills, government bonds and other financial paraphernalia all tacked to, or propped against, what looks like a handsome chest of three wooden drawers. Everything is painted with such meticulous detail that we feel we could snatch one of these bills out of its sequence, or even gratefully accept that cigarette which is sticking out at such a curious angle from the tin of Bond Street Pipe Tobacco. But there is much, much more to it than this. In fact, this is a seemingly matter-of-fact painting which we could happily ponder for days at a time, and still not get to the bottom of its mysteries.

The date of the painting's making is significant: 1937. That date relates directly to the painting's odd title. Why is déjà vu spelled in this truncated way though? Kaye is drawing our attention to movements of the Dow Jones Industrial Average – DJIA – over a period of almost a decade, and if you look very carefully you will see those words spelled out directly above the painting's title, which is at the very right hand end of this strange rising and falling of American currency.

This trajectory – which is half way between an over-ambitious V and a truncated W – shows the progress of the DJIA between 1929 and 1937, a period of heady rises and terrible falls. What is more, the long downturn in the market may not yet be over. It breaks off as it is still plunging.

Every detail looks snatchable or peel-off-able. And yet even its particular brand of extreme illusionism is somewhat illusory. How are these bills attached to these drawers? Some of them are held in position by threads secured by screws. Others appear to hang suspended in the air. Remember what happened as a child when you rubbed a balloon on your elbow and attached it to the wall? Some kind of miracle seems to be happening to some of these objects. They are being held in position by nothing. That which holds money secure is itself illusory – in short, this seems to be a statement about the nature of money. And then there are the drawers themselves, the way they are bevelled, the way they seem to be underscored by shadow. Are they not bevelled in ways which seem to run counter to each other? We see both above the bottom drawer and below it (but only on the right) – that is surely an impossibility, a trick. It simply could not happen. Or could it? And are they really projecting outwards? Why then does the bottom frame of this piece of furniture appear to be set in front of these drawers? And if they are indeed drawers, where are the handles that we would need if we were to pull them out? And where is the keyhole for that key which hangs, oddly suspended, in the centre of the painting? Is that silver coin concealing the keyhole? And then there is the matter of Otis Kaye's own initials, OK. How many times can you find those initials in this painting? Look at the extreme top left and top right. There they are all right, simulating a bit of ornamentation. But can we really be sure that OK means Otis Kaye? Perhaps he is merely reassuring us that things will be OK after all in this world of financial turmoil.

And what is the meaning of that thread which appears to hang from the nib of the fountain pen? And are we to take comfort in that tiny New Deal badge which is so close to the hazardousness of that riffle of playing cards? Or will tomorrow's newspapers repeat what the press cutting says which peers out so coyly from behind that majestic 500-dollar bill: STOCK CRASH?

ABOUT THE ARTIST Otis Kaye (1885?-1974) began to paint currency in 1917. His work appears in part to be an anachronistic throwback to other great American trompe-l'oeil painters of the 19th century, but Kaye injects into his work a 20th-century mood of urgency and anxiety.