Collectors are paying top dollar to be painted by famous artists—even if it means looking silly or grotesque. How an unflattering image became an art-world status symbol. Via WSJ.

Greek businessman Dakis Joannou was posing for a portrait by artist George Condo when he noticed a tuft of hair sprouting from the side of his head on the canvas. He interrupted the painter.

“I’m not worried about the teeth sticking out of my cheek, but I am worried about the hair sticking out of my face,” Mr. Joannou told him.

With a few brush strokes, the artist, who is known for painting surreal faces with screwball features, limited the hair to traditional spots just over the ears of the 71-year-old collector. The work by Mr. Condo, whose canvases typically command $450,000, now hangs in a privileged spot by a fireplace in the living room of Mr. Joannou’s Athens home. It’s one of three portraits Mr. Condo painted of the collector, who appears alternately with lime-green ears, a bulbous blue clown nose and an endless chin. Mr. Joannou owns them all.

The portrait has long been a symbol of the relationship between an artist and a patron. Throughout most of art history, commissioned portraits ennobled their subjects—showing them surrounded by symbols of wealth and virtue, perched regally on a steed or even transported into a New Testament scene. The artist, who depended on the patron for money and support, was typically happy to oblige any demands.

Today, portraits may be deliberately ugly, filled with palpable angst or defiantly abstract. The works are more about scouring the psychological depths or playing with the concept of portraiture than about illustrating a patron’s smooth likeness.

These portraits reflect a shift in the power dynamic between collectors and artists. Contemporary art stars are wealthy and famous in their own right. Many of them view commissions as favors, not a necessary part of business. And collectors are willing to play by portraitists’ rules for a canvas they think will reveal something profound about them—or demonstrate their special relationship with a sought-after artist.

Here are some sample portraits from our collection. Do the Ugallery pieces reflect this trend?:

Alan Taylor Jeffries “The Stranger”

Jeanette Jones “Mango”

Scott Bergey “Andrea at the Kunsthaus”

Kimia Kline “Alice”

Sharla Hammond “Untitled (Man)”

Kelly Hutchison “Pope of Trash - John Waters”