I’m Obsessed with This Painting of a Distressed Lindsay Lohan

Harley Wong
Aug 26, 2020 4:04PM

Sam McKinniss, Lindsay, 2019. Photo by Charles Benton. Courtesy of the artist, JTT, and Almine Rech.

When Lindsay Lohan was arrested and charged with her first DUI, I was almost 10 and a half years old. It was May 2007, and all my favorite starlets were spiraling. That February, Britney Spears had shaved her head, and by June, she was asking fans if she should title her then-upcoming album OMG Is Like Lindsay Lohan Like Okay Like, before settling for Blackout.

I consider myself adept at identifying LiLo’s impromptu paparazzi photoshoots in her car—from posing with Britney and Paris Hilton in 2006, in an image that the New York Post affectionately headlined “Bimbo Summit”; to being passed out in a gray hoodie in 2007, in a pose resembling Bernini’s Ecstasy of Saint Teresa (1647–52). However, the scene from Sam McKinniss’s painting Lindsay (2019) evaded me.

I felt a close affinity with LiLo ever since she starred in the Disney Channel movie Life-Size alongside Tyra Banks, and I saw my freckled face reflected back to me in 2000—before freckles were considered cool. I rooted for her through her rise and premature fall from Hollywood’s good graces, consumed by MTV’s and VH1’s play-by-play of her dysfunctional family drama and juvenile catfights with Hilary Duff, Scarlett Johanson, and Paris Hilton over some subpar boy. Instead of painting LiLo at the height of such tabloid infamy, McKinniss alludes to the accumulating rubble. In his pop-cultural spin on the venerated genre of history painting, McKinniss depicts the contemporary tragedy of Lindsay Dee Lohan.

Now in the age of himbos, I spent over an hour scouring the depths of abandoned celebrity gossip blogs triple-checking the source material for McKinniss’s portrait of a visibly distressed LiLo. With her disheveled hair and bright red lips fixed into a permanent sneer, the former child star is seen through her windshield gingerly grazing the steering wheel with a cigarette in hand. Through the lens of the relentless paparazzi, McKinniss meditates on the unseen but omnipresent forces responsible for the young starlet’s destruction.

With all the visual cues of a paparazzi shot, I mistakenly dated the scene in McKinniss’s Lindsay to the mid-2000s golden age of tabloids, characterized by gross invasions of privacy and paparazzi upskirt photos. (The latter led to Britney’s iconic line “They’re still gon’ put pictures of my derriere in the magazine” in her 2007 comeback single “Piece of Me.”)

To my surprise, the reference photo was actually taken on July 22, 2012. By then, Britney had already cemented her place as a pop music chart-topper with Femme Fatale, but LiLo’s notoriety had long faded. It was nearly a decade since she released her 2004 hit single “Rumors”—in which she cried, “Can you please respect my privacy?”—and her party-girl ways, magnified by intense media scrutiny, overshadowed her on-screen talent. Her filmography was marred by repeated flops, starting with Just My Luck in 2006, then Georgia Rule in 2007—which was eclipsed by production drama when a leaked letter from a producer compared her to a “spoiled child.”

In McKinniss’s painting, LiLo looks as messy as she did in the mid-2000s and not a day older, though here she’s depicted leaving the Chateau Marmont in West Hollywood, sans fender bender (yet she did get into one three days later). Earlier that month, she was sentenced to 90 days in jail for violating probation for a 2007 drug case. Photos of LiLo crying in court and close-ups of her manicured nails, which revealed the words “fuck u” painted on her middle finger, are now memorialized as memes.

McKinniss’s Lindsay debuted to the public in the artist’s solo exhibition “Jonathan Taylor Thomas” at JTT in February 2020. The Biebers (2020) hung on the opposite wall, depicting Justin and Hailey Bieber through a similar paparazzi lens. In it, the couple sits in their car’s black interior and look off to the side, dead-eyed. That canvas is more than triple the size of Lindsay, and yet contains none of the latter subject’s “it” quality, as if to say: They don’t make stars like her anymore.

Harley Wong