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Rembrandt’s Portrait of a Lady with a Lap Dog stands out in the AGO’s collection.Sandra Webster Cook

Hanging on a wall in New York's Whitney Museum of American Art is a portrait of Gertrude Vanderbilt Whitney in a moment of languid grandeur. Robert Henri painted the rebellious patron of the arts, sculptor and founder of the gallery in 1916. On a wall nearby is her niece Gloria Vanderbilt – no stranger to the lens of renowned photographers – captured by Gordon Parks in 1954. The two works are among more than 200, spanning the early 1900s to today, that are included in Human Interest: Portraits from the Whitney's Collection, which runs though Feb. 12.

In a timely exposition for our selfie-crazed age, the exhibition explores portraits in all their varying themes and mediums. In the show, familiar faces mingle with unknown subjects: artist Cy Twombly captured by fellow artist Robert Rauschenberg in Rome; Cindy Sherman's tragic society portrait series; works by photographers Robert Mapplethorpe, Man Ray and Richard Avedon, all of whom recorded the socially prominent on film. Each one, in the words of French poet and art critic Charles Baudelaire, "always appears to me like a dramatized biography."

For Alexandra Suda, curator of European art, and R. Fraser Elliott chair, Prints and Drawing Council at the Art Gallery of Ontario, a successful portrait captures two things: "What a person wants you to know about them and what the artist sees beneath that surface." Brenda Bury, Canada's preeminent portraitist who counts Queen Elizabeth II, Margaret Thatcher, John Diefenbaker and a plethora of well-heeled social doyennes among her subjects, says: "Looking at the portrait the viewer should recognize a fellow human. Machines, such as cameras, don't know the difference between the living and the dead," she says. "Painters are required to."

High society's link to portraiture is long established. "It was particularly important in 17th-century Holland," Suda says. "Establishing your social status through portraits by the artists Frans Hals [or] Rembrandt amongst others was key." By the 18th century, when wealth and power shifted and those with newfound affluence became a part of high society, portaiture became the most coveted luxury good. When photography democratized portraiture in the 20th century, the painted portrait took a dive. And when photography became mainstream, those who could afford it, went back to oil on canvas.

Included in the Human Interest exhibition are a series of screen-printed portraits of socialite and art patron Ethel Scull by Andy Warhol, aptly titled Ethel Scull 36 Times. Produced in 1963, they are among the thousands of Warhol pieces made of various social creatures during the artist's heyday. The prints were the ultimate status symbol of their time and remain collectible, even to buyers with no familial connections to the pop-art subjects.

The collection of the Art Gallery of Ontario is rich in portraiture. Among the works Suda finds most compelling is Portrait of a Lady with a Lap Dog by Rembrandt van Rijn, completed around 1665. "All of the attributes of the young woman's prominent social status are on parade – her luxurious dress, expensive jewellery and fashionable canine best friend," she says. Suda also points out the subject's far away gaze (a quality Cindy Sherman recreated in her 2008 society portrait series) and muted expression that she says, "make you wonder if she's happy or sad or even regretful?"

"Nobody gets painted if they are not liked by anybody – that's true isn't it?" says Bury. "You don't want a picture of somebody you can't stand!" Bury says the key transition in the medium that she has witnessed over the years is that her female subjects have evolved from ball gown-wearing hostesses to boardroom powerhouses. "I have noticed that the women are now of achievement too," she says. "It used to be that women were not the chairmen of boards, and now very often they are."

Little has changed about Bury's creative process, however. "People can only really do, let's say, five or six sittings," she says. "One does the clothes separately; if they are robes they leave them behind, if they are complicated evening dresses they leave them behind." Bury compares the exercise to an interview. "I said to the Queen, 'you must get rather tired of sitting for your portrait?' She said, 'the artists are not the most tedious people with whom I spend my time.'"

The one thing that Bury never does – and that many less-established artists do – is work from photographs. "The intrinsic value of a painting done by photographs is nil," she says. "[Painting from a photograph] is like comparing seeing a film with Angelina Jolie, with meeting her – these are two different things." Should you fancy yourself – or somebody you can stand – the subject of one of Bury's works, a formal family portrait in oils will cost anywhere between $15,000 and $30,000, while drawings or pastels are priced in the $3,000 to $6,000 range. Something to add to next year's holiday wish list, perhaps?

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