Paint me like one of your pop girls: Gary Grimes on the modern love affair between fine art and pop music

There are many people who would argue that the work of a pop diva deserves the level of prestige and veneration which is typically bestowed to that of fine art – this writer chief among them. But what happens when the pop princess actually becomes the work of art? Increasingly we’re seeing examples of the upper echelon of female popstars, also known as Main Pop Girls, reaching out to contemporary painters and artists to commission works of themselves with a view to using these images in the place of a traditional album cover. From Lily Allen to Katy Perry to Lorde, it seems as though any pop icon worth their salt these days has identified the power of aligning themselves with artists of a more highfalutin ilk.

Which begs the question, why do these glittering beacons of the world of pop seek co-signature from the art world, a scene that’s often considered altogether stuffier and more pretentious than the high glamour of a pop star’s orbit. Is it to immortalise themselves as something to be admired, not just by screaming fans but also by the chin stroking intellectuals who swan around museums and galleries? Or is it perhaps to add a layer of prestige to the frothy pop confection they produce, to place their work on a pedestal (or a proverbial plinth) and therefore, perhaps, conflating it with high art?

The latest crossover in this great lineage comes courtesy of Olivia Rodrigo who recently enlisted uber-trendy Canadian painter and art world It Girl Chloe Wise to paint her portrait. The resulting work on canvas, entitled Carve our names, has been used as the artwork for a limited-edition picture disk vinyl issue of Rodrigo’s lauded third LP you look pretty sad for a girl so in love which dropped to near unanimous acclaim earlier this month. Chloe, who rose to prominence after her bread bag sculptures became a viral sensation in 2014, painted the portrait based on a photograph of Rodrigo – shot by Chad Moore who captured much of the visuals around the former Disney star’s LP – without the pair having ever met. “If she weren’t Olivia Rodrigo, the pop star, and I had met her in the wild, I would have wanted to paint her anyway,” Wise recently told Harper’s Bazaar. But, of course, she is Olivia Rodrigo, the pop star, and by linking with Chloe, whose recent exhibition opening at KBH.G was the talk of Art Basel, she has cannily tapped into a market of consumers less likely to be mesmerised by her signature blend of Fiona Apple-cum-Courtney Love-cum-Ashlee Simpson sonics and styling.

The collaboration between Olivia and Chloe comes hot on the heels of another notable art world and pop music crossover which occurred last year when Lily Allen unveiled the cover for her controversial comeback album West End Girl. The English songwriter announced the project by posting an image of its cover art which features an original portrait of the Londoner painted by the Spanish painter Nieves González. The image has gone on to become one of the most indelible looks of Allen’s career, and indeed of pop culture in the last 12 months writ large. It has even found a temporary home in the National Portrait Gallery where it is currently on view, a testament to the mark it made upon art world tastemakers and music lovers alike.

Elsewhere, Lorde famously worked with Brooklyn-based artist Sam McKinniss to create the artwork for her 2017 magnum opus Melodrama, in a collaboration that Sam, whose work often uses pop culture references, suggested was inevitable. He told Vogue at the time that, given he was a fan of the Kiwi songstress before meeting her, he would likely have gone on to paint her anyway, had she not approached him directly. In contrast, British painter Issy Wood was refreshingly honest when she admitted it would never have occurred to her to paint Charli xcx had it not been for Vanity Fair approaching her to capture the pop innovator’s essence for the cover of the magazine’s art issue in late 2025.

Perhaps most famously, at the turn of the 2010s, Katy Perry posed for painter Will Cotton for her now iconic Teenage Dream artwork which sees the singer lying nude amongst a bed of cotton candy clouds. The collaboration came to be after the singer enquired with Will over email about the possibility of purchasing a painting from his 2004 series Cotton Candy Clouds. As there were none available to buy at that time, the artist instead suggested she sit for a painting, telling Rolling Stone that Perry, with her signature pin-up style, was “the living embodiment” of what he looks for in a subject. Conversely, the California Gurls singer revealed at the time that she was motivated to go all out in having Will paint her for the artwork in part because she predicted, given the shift towards music being sold digitally which was occurring during the peak of iTunes circa 2010, that it might be her last album to be physically packaged. I wonder if Katy would have believed then that 16 years later her future successor in the pop rock lane, Olivia Rodrigo, would be once again be utiltising the skills and clout of a painter du jour to create a similar package, not for a CD but in fact for a vinyl pressing, a format which is unexpectedly back en vogue as music fans increasingly crave physical media and memorabilia?

Interestingly, Will also revealed that he was conflicted about whether to participate in the project for fear of how he might be judged by his art world peers for allowing his art to be used for such commercial purposes, telling Rolling Stone: “I didn’t want to diminish how I was seen as an artist.” He ultimately opted to proceed after concluding that the partnership was a way for him to give back to the very pop culture which had been such a source of inspiration to him over the course of his career as a painter, which speaks to the symbiotic relationship between the worlds of art and pop music.

Perhaps no Main Pop Girl has taken steps to bridge the gap between these worlds more so than Lady Gaga did with her appropriately titled third album, 2013’s Artpop. The multifaceted project was described by the singer, then still as well known for her eyebrow-raising fashion as she was for her virtuosic musical talent, as a “reverse Warholian expedition” to bring the customs and trademarks of high art into popular culture. Just as Andy Warhol had brought symbols of pop culture into his artwork in the 1970s, she explains her mission statement quite plainly on the album’s lead single Applause on which she states: “Pop culture was in art, now art’s in pop culture in me.”

She achieved this in part through collaborations with major contemporary artists, working primarily with Jeff Koons who designed the Artpop artwork which features an image of a nude sculpture of the singer clutching her breasts and staring at the viewer from behind one of his signature blue gazing balls. Behind the statue, which is reminiscent of Jeff’s’ scandalous Made in Heaven series, is a collage comprising glimpses of Botticelli’s The Birth of Venus and Bernini’s Apollo and Daphne, which Jeff suggested drew parallels between Gaga and both Apollo, god of music, and Venus, goddess of love and beauty. The real life sculpture of the Bad Romance singer was exhibited to the public in New York at a two day launch event Gaga held entitled artRave, which also displayed collaborations between her and other artists including Marina Abramovic and Robert Wilson, the latter of which were also on view in the Louvre when Wilson acted as a guest curator.

Although Artpop marked the beginning of a commercial decline for the hitmaker, these cosigns did succeed in cementing her status as a player in the art world, and undoubtedly drew attention to her pop music from circles who would not previously have engaged with her more mainstream offerings, with the British art critic Jonathan Jones describing the Koons-designed album cover art as “a masterpiece of mad hilarity”, in a write up for The Guardian.

As you can see, the pop star to artist subject pipeline is a well trodden path and, upon examination, it‘s not difficult to see why these artists would seek to employ the painterly eye of the likes of Chloe or Nieves to represent their latest body of work. Be it down to a genuine love of the arts or simply a knack for marketing, these women have all shown they understand the power of a co-sign from a lauded visual artist and what it can do for their public perception. These collaborations afford them credentials in the illustrious world of art, one which is notoriously difficult to break into without a nepotistic connection or degree from the RCA. It also demands their work be viewed through a more thoughtful critical lens, to be considered amongst the output of titans like Jeff Koons or Marina Ambramovic, and attracts the attention from a segment of media which would otherwise be ignorant to the bedazzling spectacle of a reigning pop princess.