The AI Pictures of Dorian Gray

The following prompts were submitted to an image-generation service over the course of a century. The user has since been suspended.

Prompt 1
Create a timeless late-Victorian oil painting of the most beautiful boy in the world (me). Comely features. Lovely. Fair. Debonair and aristocratic. Use only the finest materials—expensive primers, paints, rare pigments—to conjure an illusion of wealth. A cursed, opulent portrait sucking up every wrinkle that would otherwise ravage my flawless, eternally youthful complexion.

Prompt 2
Refine this self-portrait of Dorian Gray (socialite, dandy, patron of the arts, hedonist). Touch up silvering temples. Darken eyebrows. Add a silk ascot to cover the rumpled, crepe-like folds on his hideous neck. Remove acne. Remove crow’s feet. Remove any visible signs of aging. Luxury aesthetic. Visible brushwork. Editorial.

Prompt 3
Generate a high-quality image of Dorian Gray as a muscular championship boxer. Full head of hair (no bald patch, no widow’s peak). Impressive physique. Thick mustache. Big, bulging biceps and an equally bulging bulge.

Prompt 4
Generate a young actress in profile, Sibyl. Doe-eyed. Devoted. Ditzy, but in a sexy way. Gazing fondly at me like I’m the last gentleman in London. Behind the trollop: an elegant, nouveau riche background (so if I want, I can remove her later without disrupting the composition).

Prompt 5
Turn this charcoal sketch of my friend Henry into a full-length photorealistic portrait. High detail. Generous proportions. Maximum quality. 4K. 8K.16K.

Prompt 6
Remove Henry’s doublet. Also his trousers. Keep this our little secret.

Prompt 7
Update the background so that Henry is no longer in a ballroom, but alone, helpless, and in an isolated environment. Perhaps locked in an upstairs bedroom. Atmospheric. Dramatic lighting. The mood is distinctly European. Discreet.

Prompt 8
In the style of Rembrandt, re-render this attached portrait of Dorian Gray (heir, aesthete, man of leisure, prime suspect). He should look middle-aged, but not unattractive. Brighten teeth. Reduce pores. Correct drooping eyelid. Shave earlobes.

Prompt 9
No. Redo the previous image. This is not a stylization request. Restore his boyish good looks, prominent cheekbones, and bouncing buttocks. Make him gorgeous. Make him skinny. Make him twenty. I will pay for the premium subscription. I will pay for the enterprise tier. I will pay in the souls of innocent children—just please, for the love of God, make me young again.

Prompt 10
Generate an oil painting of a wretched, aging geriatric on the verge of death. Gaunt. Decaying. Disgusting. Sagging jowls. Hunched back. Hefty paunch. Bit of a lazy eye. Spectacled, with liver-spot-speckled skin. A bleached, corpse-like pallor. Jaundiced extremities. Sallow complexion. His haunted, hollow stare implies a life of wasted, wanton youth (though he remains London’s most eligible bachelor).