In an era dominated by “blockbuster” exhibitions devoted to leading artists or major movements, it is brave to mount a show dedicated to trompe l’oeil. Historically, the practice of painting so realistically as to deceive the eye has been dismissed as artistic sorcery, an opportunity to show off technical bravura rather than make serious statements.

‘Escaping Criticism’ (1874) by Pere Borrell Del Caso

But the curators at Palazzo Strozzi have been fatally bewitched themselves. Illusionism, as trompe l’oeil is sometimes known, raises fascinating issues: how the eye distinguishes the real from representation; the relationship between art and science; consideration of socio-historical ways of seeing; an insight into the artist at play. Here however, such possibilities prove to be an embarras de richesse. Determined to cover all bases, the exhibition never fully engages with any of them.

It opens promisingly with “Escaping Criticism” (1874) by Catalan painter Pere Borrell del Caso. Showing a boy climbing out of a frame, it is a masterpiece of foreshortening and chiaroscuro which triumphantly passes the test of a true trompe l’oeil: you want to touch it just to check it isn’t really three dimensions.

Next to it stands a woman with a child in a pushchair, which on closer inspection turns out to be a hyper-realist sculpture by contemporary artist Duane Hanson. Concerned with the tension between image and reality, hyper-realism is arguably a postmodern equivalent of trompe l’oeil painting. The presence of Hanson’s work promises a fruitful cross-historical dialogue, yet this is not pursued.

Instead we are treated to a vast, ahistorical jumble of styles, epochs and mediums that includes not only painting and sculpture but also intarsia carving, illuminated manuscripts, furniture, waxworks and porcelain. Some are true illusions; many are not. Baroque anatomical waxworks, for example, possess a spooky realism but were designed more to shock and titillate observers than fool them. With so much on show that is so tenuously linked, the lack of chronology is a serious flaw.

Although irritatingly scattered about, one of the pleasures is a clutch of paintings by the French movement, Trompe-l’œil/Réalité, started by Henri Cadiou in 1960. Cadiou’s “The Tear” (1981) shows a perfect craquelure-textured replica of the Mona Lisa emerging from a paper wrapper, whose crinkles, tears, rips and adhesive tape are breathtakingly lifelike. The playfulness has an uncanny undertone: it is an expression of anxiety around the real as much as an affirmation.

Art’s ability to both celebrate and disconcert reality manifested itself in the classical era. A passion for naturalism, albeit idealised, was the signature of ancient Greek art. Yet the rapport between image and reality was fraught with conflict, causing Plato to condemn artists as dangerous peddlers of fantasy.

Such wary fascination with representation is summed up by an anecdote recounted by Pliny the Elder in which two ancient Greek painters challenge each other to a trompe l’oeil duel. Zeuxis paints a bunch of grapes so realistic that birds try to peck at it. But his rival Parrhasius trumps him by painting a curtain that Zeuxis tries to open to see the artwork he believed lay underneath.

Greek mimesis strongly influenced its Roman successors. Giving the illusion of extra windows, rooms, shelves and niches, trompe l’oeil was a key element in the decoration of Pompeian villas. Though the Florence curators highlight Pliny’s tale, the only ancient work is a shabby Pompeian still-life of dead game birds.

Along with linear perspective, trompe l’oeil disappeared in the Dark Ages and only reappeared – apart from a foray by the late Duecento phenomenon Giotto – in the Quattrocento. Italian painters had developed an understanding of geometry by then, while their Flemish counterparts were pursuing a passion for lavishly detailed interiors with vases, mirrors, books and scientific instruments often set in niches or on shelves.

These new techniques gave Renaissance maestri the tools to execute trompe l’oeil. Tucked away at the end of the exhibition are several Quattrocento gems, including a 1447-48 painting of St Mark the Evangelist by Andrea Mantegna showing the saint resting his elbow on a windowsill next to a tantalisingly tangible apple.

With the dawn of the Baroque, the genre came into its own as Catholic painters transformed churches and palaces into soaring, faux-architectural heavens. Trompe l’oeil was equally widespread in the Protestant north. An exquisite example by the 17th-century Dutch artist Barend van der Meer depicts a bunch of grapes in the foreground of a niche with a butterfly – a typical trompe l’oeil trick – perched on the edge.

As the home became an emblem of prestige, wealthy householders commissioned artists to pay homage to their possessions. Particularly marvellous is the “Cabinet of Curiosities” by 17th-century Flemish artist Domenico Remps, a cornucopia of insects, scientific instruments, cameos, engravings, paintings and a creepy, coral-sprouting skull – an elaborate vanitas which both celebrated the earthly world and exposed its inevitable decay.

In an era which saw representation of human figures as the highest form of art, why did painters choose to execute these lowly subjects with such painstaking detail? Were they just playing? Or did they have a premonition of a postmodern preoccupation with image and image-making that trompe l’oeil permitted them to explore? For all its frustrations, let’s hope this show is the first of many on an intriguing genre.

Continues until January 24