Art Institute of Chicago — Chicago, IL, USA

He turned a square canvas onto its corner to hang like a diamond — not a one-off trick, he kept coming back to the format for years.

Took him something like two years, from what I can find — a pile of small studies done out at the park, then the big one built up indoors. The speckled border round the edge is his as well; he added it later so the thing wouldn't have to sit inside somebody else's gold frame.

The models were apparently his sister and his dentist, and it supposedly won him $300 and instant fame overnight. People still argue about whether he was making fun of farm folk or standing up for them — he insisted it was the second.

The woman in the chair was a pianist who ran with a crowd of painters, writers and musicians. Apparently he painted her many times and the two stayed close friends for years, even after her marriage ended.

The woman reading is Madame Hessel — according to what I've read, she was his art dealer's wife and one of his closest friends, and he painted her over and over for something like forty years. This is her on holiday at a house by the Normandy coast.

By 1913 Kandinsky had mostly let go of recognizable scenes, chasing what he called the "inner sound" of color instead.

The man in it was a rich young aristocrat with a habit of ordering paintings of himself — this was one of several he commissioned from the same painter, going by the museum's own notes. His father, I gather, had been a heavyweight in French law and politics, so the family was well used to being looked at.

It's the old Greek story — a princess chained to a rock as an offering to a sea monster, waiting on a rescue that's supposedly on its way. They say the painter spent twenty-odd years working in nothing but charcoal black before he let colour in at all.

This wasn't made to hang on a wall at all, apparently — it's a full-size design for a tapestry, painted so the king's weavers had something to copy. The set it belonged to went into a palace dining room. Cheerful stuff to eat your lunch under, I suppose.

This type of scene is called a bodegón — Spanish for pantry — basically a kitchen snapshot with someone working in it. According to the museum's own notes, the woman here was likely enslaved, part of a household connected to Velázquez's own family. Nobody's ever put a name to her.

For a long time this hung under 'unknown Sevillian painter' — only fairly recently did anyone decide it's an early Velázquez, from before he'd really found his style. The purple cloth is apparently a deliberate touch too, a color tied to preparation, since John's whole story is about getting the way ready for someone else.

Wikipedia says he spent his summers in a small Bavarian town, painting it over and over and brighter each time — and a couple of years after this he gave up painting recognisable things altogether.

Delaunay painted the Eiffel Tower more than two dozen times, splitting it into fragments and colour rather than showing it whole.

Malevich showed these without frames and wouldn't say which way up they went — he thought a fixed top and bottom was just another assumption people had gotten used to calling natural.

I couldn't turn up much on this exact one, but Mondrian returned to this same farm and its reflection again and again in these years, like something about it wouldn't let him go.

According to the museum's blurb, he specialised in painting things so real they fool your eye — burnt-down candles, battered lamps, stuff on its way to the bin. They say he stopped showing in galleries by 1890 and just painted for neighbours near his New Jersey home.

Gris was close with Picasso in Paris and got called his disciple early on — not exactly a compliment, from what I can tell, but he'd carved out his own geometric style by the time he painted this one.

Before he helped start De Stijl, van Doesburg apparently spent a stretch working through Cubism, breaking a room and a figure down into flat, overlapping planes like this one. It's one of the pieces people use to trace how he got from drawing people to painting nothing but lines and blocks.

They say Gris started gluing in real newspaper scraps around 1913, following what Picasso and Braque had already been doing — this one keeps a strip of actual print sitting right next to the painted glass. The oval shape wasn't the usual choice either; most still lifes from this crowd were square or rectangular.

From what I could find, the man with the beard was a sculptor, and a friend — apparently he sat for him more than once. They were both fairly big names in Switzerland around then.