The 100 best paintings in London: 50-41

WHEN? 1624
WHERE CAN I SEE IT? Wallace Collection  
I LIKE IT See also 'Girl at a Window'

Is that a gold rapier pommel protruding from the crook of your doublet, or are you just pleased to see me? Can there be a character in art history with more ‘hello ladies’ swagger than ‘The Laughing Cavalier’? A froth of lace and embroidered silk topped with a face you either want to kiss or slap, he stands, one expensively clothed hand on his hip, justly famous as a swaggering star of the Wallace Collection. Yet, he’s not really laughing (smirking, more like) and he’s not a cavalier, either. In fact, this rakish young man is thought to be a textile merchant. His clothing certainly has been given a great deal of thought and the fanciful motifs of its decoration are said to allude to the pleasures and pains of amour. A lover, not a fighter, then.

WHEN? 1987
WHERE CAN I SEE IT? This painting is part of the Tate collection but currently not on display. Check Tate Modern or Tate Britain to see when it will next be on show.
I LIKE IT See also 'Cage 1-6'

A schematised building – just a blue rectangle, really, with white marks representing the windows – is surrounded by dark geometric forms. What are they, exactly? Bow ties? Butterflies? Or perhaps simplified rooms seen in perspective? There’s an ambiguity in the work of this Dutch artist (born 1950) that, combined with a deadpan approach, puts him the same artistic family as a surrealist like René Magritte. Daniëls is a ‘painter’s painter’ – an artist widely admired by his peers for pushing the genre in new and interesting directions, yet who hasn’t had the commercial success or fame he perhaps deserves. That Daniëls suffered a brain aneurysm in 1987 and only recently began painting again just adds to his mystique.

WHEN? 1902
WHERE CAN I SEE IT? Tate Britain
I LIKE IT See also 'Nude Girl'

John painted many solitary women, but here we see the prototype: the artist as an isolated, rather sad spinster – an awful word, but appropriate surely to 1902, and to this austere figure, with her bright blouse muted somehow by dark, pensive eyes, black shawl and the jet brooch (mourning jewellery, perhaps?) at her throat. Still, there’s no mistaking her strength: those eyes pierce both the painting (after all, it’s her vision we’re viewing) and the future, where John would come out of the ‘female artist’ ghetto to overtake, in reputation, her more clubbable brother Augustus and many other contemporaries who benefitted less from being talented than from being male. Spinster, as a job title, is obsolete; painter is anything but.

WHEN? 1925
WHERE CAN I SEE IT? Tate Modern
I LIKE IT See also 'Weeping Woman'

Picasso's macabre, landmark piece appeared in a journal illustrating André Breton's manifesto ‘Surrealism and Painting’. It displays the angular, jagged shapes that he was more conventionally associated with, but also marked a shift in Picasso’s style, which, laden with surreal symbols, refer to the artist’s failing marriage and close friend Carlos Casagemas’ suicide.

WHEN? 1909-10
WHERE CAN I SEE IT? Tate Britain
I LIKE IT See also 'Self-Portrait'

‘Nude Girl’ is a paradigmatic portrait by this woman out of time. After attending the Slade, the only art school that would accept women in 1895, John lived a life of penury, squatting in London and sleeping rough as she travelled through France (taking time out to be Rodin’s lover). The nude girl of the title is a testament to John’s iconoclastic worldview, which morphed into a spiritual Catholicism as she got older. The young figure’s stare is questioning rather than naive. Her elongated body leads to large, almost masculine hands, while the colour of the background, the cloth on her lap and her eyes and skin are all pallid, only fractionally different in tone. There is no male gaze here. Rather, the girl looks back at the viewer, aware of their stare and its multiple implications.

WHEN? 1607
WHERE CAN I SEE IT? National Gallery
I LIKE IT See also 'The Supper at Emmaus'

Not one to suppress his appetites, the Italian painter and every-which-sexual was a friend to rent boys and prostitutes alike, and his violent streak led him, famously, to assault a waiter’s face for bringing him an artichoke cooked in butter instead of olive oil (honestly, though, what was the chef thinking?). Unsurprisingly, Michelangelo Merisi (as Caravaggio was born) had to flee Rome after murdering someone – over a woman, a tennis match, nobody remembers – and tried to endear himself to the residents of Malta before his temper got the better of him and they threw him out too. Amidst all this bridge burning, Caravaggio also managed to be one of the greatest painters of all time. For this work, done in the last few years of his life, he used his own likeness for John The Baptist’s severed head. Truly, the one thing Caravaggio was never accused of was subtlety.

WHEN? –
WHERE CAN I SEE IT? British Museum
I LIKE IT See also 'Portrait of Margharete de Geer'

This portrait of an Egyptian woman was unearthed in 1888 by the fabulously named Flinders Petrie (also the grandfather of modern archaeology). While Europeans struggled with, or just didn’t care for, perspective until it became wildly popular in the Renaissance, the Egyptians’ artistic output was already incredibly nuanced all those thousands of years ago. Unlikely to be one of the slaves that built the pyramids, the anonymous woman depicted is wearing jewellery in gold and precious stones, and fine purple cloth. What’s startling is how contemporary the portrait looks, with delicate shading on her bright clothing and sensitive details to her eyes and face. She just captures your gaze with her warm eyes and doesn’t let go.

WHEN? 1839
WHERE CAN I SEE IT? National Gallery
I LIKE IT See also 'Peace: Burial at Sea'

Turner’s most famous painting depicts the gunship ‘Temeraire’, a veteran of the Battle of Trafalgar, being towed by paddle steamer to its final berth in Rotherhithe to be broken up for scrap. It’s a work that stands as a summation of Turner’s great sea paintings – here is a relic of Britain’s declining naval power rendered as a kind of apparition, the fiery sunset behind it (Turner played fast and loose with the composition, placing a setting sun in what would have been an eastern sky) adding to its ghostlike appearance. A symbol of pride and of loss, its emotional impact endures to this day.

WHEN? 1819
WHERE CAN I SEE IT? Tate Britain
I LIKE IT See also 'A Cornfield by Moonlight with the Evening Star'

Appropriately for such a small work (it’s only inches high), ‘Ghost of a Flea’ conveys a feeling of imaginative concentration, of visionary intensity. Claiming to have witnessed a supernatural apparition, Blake depicts the insect’s spirit as a grotesque, vampiric man-monster, its tongue flicking horribly towards a bowl of blood. Whether or not you’re convinced by Blake’s story, the sheer horror of his painting is undeniable.

WHEN? 1768
WHERE CAN I SEE IT? National Gallery
I LIKE IT See also 'Mr and Mrs Andrews'

Wright’s masterpiece is an allegory of the Age of Enlightenment, with the glow from a scientific experiment outshining the lesser light of the moon, a relic from a more superstitious age, far off in the background. Yet you get the sense that Wright might not have been such a cheerleader for science if he could foresee the industrialisation that would soon transform the landscape of his beloved, native Derbyshire.