Character Studies: New Paintings by Jessica Helfand

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Character Studies New Paintings by Jessica Helfand

He was not over thirty. His eyes were very dark brown and there was a hint of brown pigment in his eyeballs. His cheekbones were high and wide, and strong deep lines cut down his cheeks, in curves beside his mouth. His upper lip was long, and since his teeth protruded, the lips stretched to cover them, for this man kept his lips closed.

Pointed chin, you’re attractive but don’t, I implore you, overdo that point. Hazel eyes, you persist in being hazel and I can’t blame you for it; but don’t retreat under my eyebrows with that excessive modesty. Mouth, you’re still my mouth, but so pale that I can’t resist rubbing those short, colorless lips with petals pulled from the red geranium in the window. (Incidentally it only gives them a horrid, purplish tinge that I promptly lick off.) As to you, my poor little white, anaemic ears, I hide you under my curly hair and secretly look at you from time to time and pinch you to make you redden. But it’s my my hair that’s the worst of all. I can’t touch it without wanting to cry. . . They’ve cut them all off, just below the ear — my auburn ringlets, my lovely, smoothly-rolled ringlets!

England.

Character Studies reimagines the faces of some our most beloved fictional protagonists as a collaboration with the authors who once created them. By introducing original character descriptions into AI and combining them with paintings, each portrait embeds its author’s voice as a core conceit, an opportunity to dramatize (and humanize) rather than optimize an imagined visual outcome. Included here are characters drawn from novels by Jane Austen, Theodore Dreiser, Henry James, Edith Wharton, and Virginia Woolf, among others.

Jessica Helfand (b. 1960) is an artist and writer. She grew up in Paris and New York City, and received her BA and MFA from Yale University where she taught for more than two decades. She is the author of numerous books on visual and cultural criticism, and was the first-ever recipient, in 2010, of the Henry Wolf Residency at the American Academy in Rome. A 2018 Director’s Guest at Civitella Ranieri and a 2019 fellow at the Bogliasco Foundation, Jessica Helfand was the 2020 Artist in Residence at Caltech. She lives and works in New
Jim Kempner Fine Art is pleased to announce Character Studies, an online exhibition of new paintings by gallery artist Jessica Helfand. The exhibition is on view through June, 2025.

All right. Close your eyes. Now open them. First time you see me. You just see me. What you would say I was?

She couldn’t say.

‘That is the whole blasted trouble,’ he said. ‘I don’t look like anything at all. Shopkeeper, lawyer, doctor, laborer, overseer — I don’t look like any of them.’

Regular features, open countenance, with a complexion! oh! what a bloom of full health, and such a pretty height and size; such a firm and upright figure. There is health, not merely in her bloom, but in her air, her head, her glance.

emma woodhouse Emma Jane Austen 1815

She was short, plump and fair, with a fine bloom, blue eyes, light hair, regular features, and a look of great sweetness; and before the end of the evening, Emma was as much pleased with her manners as her person, and quite determined to continue the acquaintance.

Her white skin had a singular look of being drawn tightly across her face; but her features, though sharp and irregular, were delicate in a fashion that suggested good breeding. Their line was perverse, but it was not poor. The curious tint of her eyes was a living color; when she turned it upon you, you thought vaguely of the glitter of green ice.

Constance, his wife, was a ruddy, country-looking girl with soft brown hair and sturdy body, and slow movements, full of unusual energy. She had big, wondering eyes, and a soft mild voice, and seemed just to have come from her native village. It was not so at all.

constance reid
Chatterley’s Lover
Lawrence

The red of the cheeks was covered with peach down; the down on the lips was only a little thicker than the down on the cheeks. The lips themselves were short and slightly drawn back over teeth of an exquisite and almond whiteness. Nothing disturbed the arrowy nose in its short, tense flight.

Her pretty little upper lip, on which a delicate dark down was just perceptible, was too short for her teeth, but it lifted all the more sweetly, and was especially charming when she occasionally drew it down to meet the lower lip. As is always the case with a thoroughly attractive woman, her defect—the shortness of her upper lip and her half-open mouth—seemed to be her own special and peculiar form of beauty.

maria bolskonaya War and Peace

Her chest soon began panting rapidly; the whole of her tongue protruded from her mouth; her eyes, as they rolled, grew paler, like the two globes of a lamp that is going out, so that one might have thought her already dead but for the fearful laboring of her ribs, shaken by violent breathing, as if the soul were struggling to free itself.

emma bovary
Madame Bovary

Jane Austen 1811

Miss Dashwood had a delicate complexion, regular features, and a remarkably pretty figure. Her face was so lovely, that when in the common cant of praise, she was called a beautiful girl, truth was less violently outraged than usually happens. Her skin was very brown, but, from its transparency, her complexion was uncommonly brilliant; her features were all good; her smile was sweet and attractive; and in her eyes, which were very dark, there was a life, a spirit, an eagerness, which could hardily be seen without delight.

A few years before, Anne Elliot had been a very pretty girl, but her bloom had vanished early; and as even in its height, her father had found little to admire in her, (so totally different were her delicate features and mild dark eyes from his own), there could be nothing in them, now that she was faded and thin, to excite his esteem.

elinor dashwood
Sense and Sensibility
x 16 inches
anne elliot Persuasion
Jane Austen
Mixed media and oil on canvas
x 16 inches

The dark pencilling of fatigue under her eyes, the morbid blue-veined pallor of the temples, brought out the brightness of her hair and lips, as though all her ebbing vitality were centered there. Against the dull chocolate-colored background of the restaurant, the purity of her head stood out as it had never done in the most brightly lit ball-room. He looked at her with a startled uncomfortable feeling, as though her beauty were a forgotten enemy that had lain in ambush and now sprang out on him unawares.

The House of Mirth
Wharton

No one who had ever seen Catherine Morland in her infancy would have supposed her born to be a heroine. They (Catherine’s family) were in general very plain, and Catherine, for many years of her life, as plain as any. She had a thin awkward figure, a sallow skin without color, dark lank hair, and strong features. She never could learn or understand anything before she was taught; and sometimes not even then, for she was often inattentive, and occasionally stupid.

She was small of her age, with no glow of complexion, nor any other striking beauty; exceedingly timid and shy, and shrinking from notice; but her air, though awkward, was not vulgar, her voice was sweet, and when she spoke her countenance was pretty.

catherine morland
fanny price
Mansfield Park
Jane Austen 1814
Mixed media and oil on canvas

The cold wind had swelled and reddened my hands, uncurled and entangled my hair, and dyed my face of a pale purple; add to this my collar was horridly crumpled, my frock splashed with mud, my feet clad in stout new boots, and as the trunks were not brought up, there was no remedy... so having smoothed my hair as well as I could, and repeatedly twitched my obdurate collar, I proceeded to clomp down two flights of stairs, philosophizing as I went.

A tall and as yet slight figure, surmounted by an interesting head and face—white skin, dark hair— he seemed more keenly observant and decidedly more sensitive than most of the others—appeared indeed to resent and even to suffer from the position in which he found himself. The beauty of his face and hands— the blackness and softness of his hair, the darkness and melancholy and lure of his eyes. He was attractive—oh, very. Beautiful, really, to her.

clyde griffiths

She was very beautiful, and even more than beautiful—strange

And the features were stranger and more monumental even than the substance in which they seemed carved by some sharp chisel, delighting in gradual hollowing of cheek and eye, in sudden cutting of bold groove and cavity of nostril and lip.

She had had many embodiments. Essentially she was perhaps of no tangible substance; a spirit, a dream, a frenzy, a conception, an aroma, an epitomized sex, a light of the eye, a parting of the lips. God only knew what she really was; Pierston did not. She was indescribable.

avice caro
The Well-Beloved

She was twenty-four as opposed to Frank’s nineteen, but still young enough in her thoughts and looks to appear of his own age. She was slightly taller than he—though he was now his full height (five feet ten and one-half inches)—and, despite her height, shapely, artistic in form and feature, and with a certain unconscious placidity of soul, which came more from lack of understanding than from force of character.

Her hair was the color of a dried English walnut, rich and plentiful, and her complexion waxen— cream wax—with lips of faint pink, and eyes that varied from gray to blue and from gray to brown, according to the light in which you saw them. Her hands were thin and shapely, her nose straight, her face artistically narrow.

She was not brilliant, not active, but rather peaceful and statuesque without knowing it.

lillian semple The Financier

She had insisted on a modern bed. Her tray was beside her and the quilt was littered with envelopes, letters and the daily papers. Her head was propped against a very small blue pillow; clean of make-up, her face was almost colorless, rose-pearl, scarcely deeper in tone than her arms and neck.

‘Well?’ said Tony. ‘Kiss.’

He had a nose like a shrike’s bill and a long vertical crease on either side of his mouth; his hair looked as if it had been permanently flattened under the heavy hat, but his eyes were what held her attention longest. Their settings were so deep that they seemed, to her, almost like passages leading somewhere and she leaned halfway across the space that separated the two seats, trying to see into them.

She was smaller and thinner than Lily Bart, with a restless pliability of pose, as if she could have been crumpled up and run through a ring, like the sinuous draperies she affected. Her small pale face seemed the mere setting of a pair of dark exaggerated eyes, of which the visionary gaze contrasted curiously with her self-assertive tone and gestures; so that, as one of her friends observed, she was like a disembodied spirit who took up a great deal of room.

Mixed media and oil on canvas

52 x 42 inches 2025 (detail)

bertha dorset
The House of Mirth
Edith Wharton

How very lovable her face was to him. Yet there was nothing ethereal about it; all was real vitality, real warmth, real incarnation. And it was in her mouth that this culminated. Eyes almost as deep and speaking he had seen before, and cheeks perhaps as fair; brows as arched, a chin and throat almost as shapely; her mouth he had seen nothing to equal on the face of the earth. To a young man with the least fire in him that little upward lift in the middle of her red top lip was distracting, infatuating, maddening. He had never before seen a woman’s lips and teeth which forced upon his mind with such persistent iteration the old Elizabethan simile of roses filled with snow. Perfect, he, as a lover, might have called them off-hand. But no—they were not perfect. And it was the touch of the imperfect upon the would-be perfect that gave the sweetness, because it was that which gave the humanity.

Madame Merle was a tall, fair, smooth woman; everything in her person was round and replete, though without those accumulations which suggest heaviness. Her features were thick but in perfect proportion and harmony, and her complexion had a healthy clearness. Her grey eyes were small but full of light and incapable of stupidity— incapable, according to some people, even of tears; she had a liberal, full-rimmed mouth which when she smiled drew itself upward to the left side in a manner that most people thought very odd, some very affected and a few very graceful.

It would never have been supposed she had come into the world in Brooklyn—though one could doubtless not have carried through any argument that the air of distinction marking her in so eminent a degree was inconsistent with such a birth.

madame merle
The Portrait of a Lady

jim kempner fine art specializes in contemporary paintings, sculpture, photography, and works on paper, with a special emphasis on contemporary master prints and outdoor sculpture. JKFA works closely with art advisors, designers, corporations and museums to expand and enrich their varied collections.

Located in the heart of Chelsea, the gallery’s three story, modernist-inspired structure–designed by architects Smith + Thompson–offers one of the few outdoor sculpture gardens in the area. The building is included in a number of books about contemporary architecture.

Their inventory includes work by artists such as Derrick Adams, Louise Bourgeois, Richard Diebenkorn, Helen Frankenthaler, David Hockney, Jasper Johns, Deborah Kass, Alex Katz, Ellsworth Kelly, William Kentridge, Jeff Koons, Robert Mangold, Robert Motherwell

Elizabeth Murray, Roy Lichtenstein, Robert Rauschenberg, James Rosenquist, Ed Ruscha, Paula Scher, Sean Scully, Frank Stella, Andy Warhol and Stanley Whitney.

Among the contemporary artists whose work they represent are Christopher Beane, Long Bin Chen, Jessica Helfand, Charlie Hewitt, Jay Kelly, Nora Ligorano and Marshall Reese, Jerry Mischak, David Mitchell, Robert Petersen, Tom Slaughter, Jim Watt and Boaz Vaadia.

A private dealer starting in 1987, Jim Kempner opened his Chelsea gallery, Jim Kempner Fine Art, in the fall of 1997. Kempner has published prints by Rinaldo Frattolillo, Charlie Hewitt, Robert Indiana, Paula Scher, Bernar Venet, as well as a portfolio of Gianfranco Gorgoni’s photographs of Robert Smithson’s Spiral Jetty among many others. His web series, The Madness of Art, is a comedic satire of the art world that is in its seventh season.

jim kempner fine art

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