The New Republic has a very good take on Art.sy and the limitations of online art discovery by Jason Farago:

 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.”

Art.sy and the Myth of the Online Art Market (New Republic)