Not every plucky startup gets a fawning profile in The New York Times on launch day, but still fewer get a shout-out from Rupert Murdoch on his erratic Twitter feed. Art.sy, the long-time-coming digital art outpost, got both. The hugely hyped website promises to introduce users to art they’ll enjoy via a sophisticated recommendation engine; the Times placed Art.sy alongside Netflix and Pandora as a means for serendipitous artistic encounters. But what has excited Wendi Murdoch and the site’s many other starry investors (Eric Schmidt of Google, Jack Dorsey of Twitter) is Art.sy’s real business, mentioned only in passing in paragraph 18 of the Times piece: brokering sales between galleries and collectors. Will it work? Perhaps, though if they do succeed Art.sy will be the exception, as company after company has failed to drag the art world into the digital age.

At the core of Art.sy is an algorithm that assesses art via a series of properties. The fancy name for these properties is “genes,” but really they’re just tags, hand-affixed by a team of art historians. (Who said we were unemployable?) There are movements, nationalities, political and social orientations, and more subjective critical categories, such as “Artist as Ethnographer” or “Fact v. Fiction.”

In one way, this is refreshing: unlike its predecessors, and in marked contrast with the naive Silicon Valley consensus, Art.sy doesn’t make the mistake of believing that contemporary art can be boiled down to formal elements. A computer just can’t discern why an Yves Klein monochrome and a Blinky Palermo monochrome have nothing in common, or distinguish between an Andy Warhol flower painting and a Sturtevant appropriation of it. At the same time, the warren of art history grads hand-coding this thing gives the game away. What poses as machine intelligence is in fact a distinctly unglamorous form of curatorial labor—the Mechanical Turk of the art world.

Once you’ve logged in and begun to explore, the connections Art.sy draws can be mildly illuminating. But more often they’re frivolous if not downright insulting; upon viewing a Joel Meyerowitz photograph of a swimming pool, I was shown other images of pools. Things also get trickier when moving from artworks to artists. Jeff Wall, among the most significant artists of the last 30 years, has been given the labels “Manipulated Photography” and “Cinematic”—and thus his closest equivalent is Gregory Crewdson, a far less subtle and indeed less important photographer. I bow to no one in my adoration of Tacita Dean, a virtuoso of analog film—so apparently I should have a look at some unknown third-rate illustrator who also carries the genes of “Woman” and “Isolation/Alienation.”

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