Hey Leonardo! by Kate Knibbs
"He seems like a dirty freak in a class of his own"
This is the inaugural entry of Know-It-All, a zine about obsession and fandom. It’s written by and for people who like to read and watch and listen to stuff. In this essay, Kate Knibbs charts her lifelong compulsion to watch every movie Leo has ever been in. To order a print copy, reply to this email with your name and address and you’ll receive payment instructions.
As a pre-teen Titanic freak, the most dog-eared, raggedy paperback I kept on my middle-school bookshelf was called Leonardo DiCaprio: Modern Day Romeo. The extremely unauthorized biography outlined the contours of DiCaprio’s early life in gloopy prose geared towards a puberty-addled audience. (Typical line: “He flashed his winning smile.”) I think I read it thirty times. I borrowed my dad’s work photocopier to cobble collages of Leo from the glossy color photos in the book’s center. Using pilfered scotch tape, I hung these homemade tribute posters to Leo on random telephone poles around our neighborhood with my friend Jessica. An equally zealous Leo fan, she made sure the i’s in “DiCaprio” were dotted with hearts. No existing copies remain, but I still remember what I wrote in careful Sharpie bubble letters on top: “Best Actor Ever!!!”
My crush faded pretty quickly—by junior high, I was all about Russell Crowe in Gladiator—but my attachment to Leo the actor didn’t waver. I’ve never yet missed one of his films. (Except the nature documentaries he narrates. You have to draw a line somewhere.) He weathered one year of dual stinkers early on (The Man in the Iron Mask, Celebrity) and he’s been a bright spot in a few mediocrities—Don’t Look Up, I’m looking at you—but otherwise his filmography is unskippable. His movies largely range from solidly rewatchable (Blood Diamond, The Great Gatsby) to spectacular (Catch Me If You Can, Once Upon a Time in Hollywood, every Scorsese collaboration). I’ll watch him clack his overly long fingernails together as the disintegrating Howard Hughes in The Aviator any day of the week, the almost-three-hour runtime be damned.
Once Leo’s delicate YA beauty coarsened into a more fungible, everyday handsomeness, he figured out how to tap into a deeply pathetic quality he laces throughout his best performances. In Baz Lurhmann’s frenetic, sometimes glib The Great Gatsby adaptation, his Jay Gatsby cuts through the gaudiness with a sheer force of longing. He plays Gatsby as the class-jumping try-hard he is—not debonair so much as frantically performing an impression of debonair. In his most recent role in Killers of the Flower Moon, he plays one of modern cinema’s most thorough cowards as the blinkered dimwit Ernest Burkhart. He first made his name as a dreamboat; he’s since made his career playing dickheads, doofs, and dumbasses.
He also basically created the playbook for actors who want to leave their teen-idol status behind; without Leo seeking out auteurs and avoiding franchises post-Titanic, we might never have had Robert Pattinson or Daniel Radcliffe’s indie careers.
But, I must admit, there is another reason my Leo fascination endures: He seems like a dirty freak in a class of his own. It’s not just that infamous insistence on dating very young models, despite his own advancing age. Or the persistent rumor that he wears headphones during sex. Or the Pussy Posse. Or the incessant vaping. Or how he’s slowly morphing into Jack Nicholson in body, mind, and spirit. It’s all of it, together, amalgamating into a celebrity persona the likes of which we will never see again: The last uncancellable man.
Every paparazzi photo and bizarre rumor deepens his alt persona of spectacular weirdo. Will we ever see the likes of DiCaprio Freak Lore again? One of my biggest professional failures is that, when I worked at a podcasting company, I failed to convince my bosses to let me make my dream podcast, “The Pussy Posse Podcast.” There is no better map key to understanding pre-9/11 Hollywood culture than Leo’s infamous friend circle, a crew that included Tobey Maguire, Entourage’s Kevin Connelly, Mad Men’s Jay R. Ferguson, and magician David Blaine. With its rancid proto-Zynternet attitude, the Posse’s aura of entitlement made the Brat Pack look like Franciscan monks. Don’s Plum, the film the Posse made together and then jettisoned after they realized it was so offensive that it might derail their careers, is so baldly misogynistic, it’s kind of nuts that it hasn’t been resurrected by red-pilled incels. Hooligans!
The week that I’m writing this, tabloids published blurry paparazzi photos of Leo hanging out on his yacht in Sardinia, recovering from a jellyfish sting acquired during a dip in the Mediterranean. He looks totally unconcerned about cnidarian venom. He has a man bun and his vape and his phone, which he is looking at in most of the photos. He took two members of the Pussy Posse on the trip, along with his 26-year-old girlfriend.
This new batch of out-of-focus shots of our lad lounging in the sun, up to his old tricks, is the celebrity-culture equivalent of a nostalgia nuke. Swap the girlfriend’s face out with any of the previous girlfriends, and it could’ve been taken yesterday or a decade ago. There’s something comforting about Leo’s calcified, wholly unreformed party-boy persona. In his art, he stretches himself, striving for something new; in life, though, he’s a man from the past. He’s forever the prince of the city, a living relic, representation of a type of celebrity meant to be extinct. Proof, however louche, that not everything has to change. It’s this quality—this debauched mirage of continuity—that draws me to Leo, especially when I’m feeling adrift. I never talk to Jessica anymore. Leo lets us pretend we’ll never have to let go.
Kate Knibbs is a writer from Chicago.