Would John Singer Sargent paint Sabrina Carpenter?

Published by

Louisa Rimmer

01 October 2025

The year is 1908 and Nancy Astor is sitting very still. It’s been two years since she moved to Cliveden, the palatial house and estate overlooking the Thames that was gifted by her husband’s family. Two years also since she emigrated from America. Today, John Singer Sargent is painting her. 

A little over a century later, 2025 to be exact, Sabrina Carpenter, by this time a global popstar, releases her seventh studio album, Man’s Best Friend. Typical for a woman flaunting a successful career in the public eye (how dare she!) the album has received a mixed reception. It’s true that it is “not for the pearl clutchers,” as she warned in an interview with CBS, with all the laugh-out-loud innuendo and upfront declarations of horniness that her audience has come to expect.

Do you want the house tour? / I could take you to the first, second, third floor / And I promise none of this is a metaphor. With a chuckle, I can’t help but think of this line, one of Carpenter’s latest earworms, as I step over the threshold of Kenwood House. 

Inside the exhibition, Sargent’s oil paintings appear to be emitting an otherworldly glow against the dark interior of Kenwood’s music room. There is something both compelling and a little unsettling about the sense of vivid, breathing life that this gives Sargent’s subjects, coupled with the dynamism of his painting style. His 1898 portrait of Daisy Leiter is particularly striking. She is captured mid-gesture, engaged and open, gazing directly at the viewer, a glimmering shawl lifting with movement. Similarly, he depicts Cora Kennard, Countess of Strafford with nonchalant confidence, holding a string of pearls loosely in her lap. She doesn’t meet the viewer’s gaze, instead turning her head and smiling at something out of frame. Cora has a whole lot more to her, Sargent seems to imply, than can be captured here. She is an individual historical agent. 

The fascination with these ‘dollar princesses,’ so-called for the cash-for-class exchange associated with their transatlantic marriages, is mirrored in the twenty-first-century cult of celebrity. The ‘dollar princesses’ were subject to widespread criticism and stereotyping from both the American and the British sides, which they had very limited agency to resist.

In the era of internet virality and its globalised gossip, the same can often be said of the modern celebrity, particularly women. This was what Sabrina Carpenter discovered, perhaps not for the first time, when the artwork for Man’s Best Friend made headlines in June this year. The cover depicts Carpenter kneeling whilst somebody in a suit stands next to her and pulls her hair. The image drew controversy, including from Glasgow Women’s Aid, who accused Carpenter of pandering to the male gaze and playing into misogynistic tropes. On the flip side, the view that the artwork is tongue-in-cheek is not unfounded. Whilst the album’s cover and title reference the patriarchal degradation of women, Carpenter’s lyrics certainly don’t let men get away with it: “You think that I’m gonna f⸺ with your head? Well, you’re absolutely right” (Don’t Worry I’ll Make You Worry), “Stupid? Or is it slow? Maybe it’s useless? But there’s a cuter word for it… I know! Manchild…” (Manchild). The album can also be considered to be simply an expression of unabashed female sexuality and that the cover, in Carpenter’s own words, plays on “being in on the control, being in on your lack of control, and when you want to be in control”. Regardless, Sabrina gets the last laugh. She responded to this backlash with a rather emphatic “I can not give a f⸺ about it”. Much like Sargent’s ‘dollar princesses,’ this pop princess has sent a reminder that she too is an individual that cannot be so easily defined.

The ‘dollar princesses’ got the last laugh too. Perhaps many of them were beyond caring about public opinion, as The Helena Independent suggested on 1 March 1891: “The American women in London may be divided into three classes – those who are in society, those who would risk their chance of heaven to get there, and those who do not care whether they are in or out!” Indeed, many appear to have been too busy reaping the rewards of their new positions to have been bummed down. 

Edith, Lady Playfair was a keen golfer who split her time between Mayfair and St Andrews. Mrs Wilton Phipps was awarded the title of Dame for her work in local government. Daisy Leiter was a gifted horsewoman and an amateur pilot. Pauline Astor was a keen gardener who developed new strains of rhododendrons and azaleas in the grounds of her Surrey manor house. And Nancy Astor, in the years after Sargent completed her 1908 portrait, became the first woman MP. 

However, the moral murkiness of Sargent’s subjects is objectively far more sinister than Carpenter’s mixed messaging and to treat them as the historical agents that they are requires an acknowledgement of this. Whose expense are they laughing at? The wealth that earned Consuelo Yznaga del Valle a marriage overseas was derived from her family’s Louisiana plantation that was maintained by enslaved workers. Mary Crowninshield Endicott Chamberlain was a direct descendant of John Endecott, considered one of the Fathers of New England, who established the region’s central role in colonisation in the 17th century. During her political career, Nancy Astor supported a policy of appeasement towards Adolf Hitler. 

There is so much discomfiting complexity at work in Heiress: Sargent’s American Portraits. These women afforded vitality by Sargent’s dynamic style are also shaped by their own brushstrokes. They are powerful and confident and somewhat liberated. But they are also flanked with the troubling contexts that accompany such vast levels of wealth and privilege. It seems to me that Sabrina Carpenter too evokes a complex picture of womanhood in Man’s Best Friend. Emerging from all of the confused public discourse is only a reemphasis of what we cannot possibly know: Sabrina herself, wholly.