Better Off Alissa Bennett

We're sitting in the sapphire-lit lounge of New York City's Algonquin Hotel, a fitting atmosphere to talk with Bennett, whose specific charisma can best be described as conspiratorial. Her dayjob is that she's a director at the Barbara Gladstone Gallery, but she moonlights as the co-host of Luminary podcast The C-Word with Lena Dunham, and has authored a series of gonzo trauma zines, published by Heinzfeller Nileisist that have afforded her the self-identified distinction of being a "historian of bad behavior." There's Bad Behavior (self-explanatory), Dead Is Better (paying tribute to fallen icons), I Expected Something Nice ("About disappointments...I think it's pretty good," she says), and Pretend You're Actually Alive ("About people with double lives...that one's pretty good, too"). Bennett's essays are first-person direct, perverse love letters to figures as tragic and desperate, conniving and misunderstood, as Milli Vanilli, GG Allin, Andrew Cunanan, infamous Hollywood madam Heidi Fleiss, and my favorite, Paula Abdul. "You were FREAKED, Paula," Bennett writes in her signature hysteric prose, reminding Abdul of a creepy bouquet of flowers she received from her stalker, American Idol contestant Paula Goodspeed: "but this poorly executed floral Trojan horse did not even begin to prepare you for what was coming. On November 8, 2008, Paula Goodspeed drove her devastated Toyota Camry to your house, parked it two doors down, and killed herself with a mega overdose of about 700 different types of medication."

I don't know Bennett's age but she has Gen-X energy, cutting a figure both unassuming and urbane. She dresses like someone raised on a culture diet of Melrose Place and John Hughes. Today she's wearing a striped cashmere sweater (vintage Balenciaga), an overcoat (Maison Margiela), faded jeans (GAP) and lived-in white sneakers (Keds). Her hair is coiffed to the side, a blasé redux of something a 60s socialite might have requested at Kenneth, and her earrings are chunky, vintage gold hoops. "I always think of my look as Jessica Fletcher from Murder She Wrote on a bike in Maine," Bennett muses. The comparisons don't end there: just like the fictional Fletcher, Bennett hails from coastal New England (Rhode Island), and is also a writer, trafficking in tales of murder, savagery, betrayal, desperation, and other felonious ventures of the down-and-out, once-famous, infamous, sometimes-unknown, probably-forgotten-about, better-off-dead, or banished-into-the-ethers-of-time.
"My general interest is that I'm obsessed with fandom," she tells me. "I'm always curious about how that brain circuit works. It's what you like about a person and what makes you relate to a stranger." She asks me if there's a celebrity death that truly shocked me, and we discuss, for a bit, Anna Nicole Smith. "Is she somehow you, but under different circumstances?" she asks. Smith was unapologetically herself and yet misunderstood, I say: a big part of fandom is the feeling that you understand someone better than everyone else does. "I agree," Bennett says. "Do you know what her favorite song was? 'Lady In Red!' That was her song that she danced to while looking for a rich husband!'"

Bennett's essays are filled with such vivid details, which she addresses to victims and perpetrators alike. Whether her recipient is dead or alive, she confronts them directly with their darkest choices, memories many people would understandably prefer to keep buried in the past. Whether it's a suicide victim, serial killer, adult film star, or Hollywood casualty, Bennett retraces each figure's steps with a forensic lust, often sourcing details from the abject fan forums and message boards of Web 1.0. "I don't know how much you frequent these fan forums online," she says, citing FindADeath.com as a personal favorite. "A thing that comes up again and again is that whenever a Brad Renfro dies or a Jonathan Brandis dies, the conditions of possibility for actually meeting that person are gone. You're ultimately blocked from meeting them and so it brings the fan and the object of desire closer, somehow. The death has a kind of accordion effect: women go online and pretend to have known these people and they write this very complicated fanfiction about them. People love to be friends with a dead person! Suffering makes people feel special. Tragedy, snobbery...it's very common." Is that what draws Bennett toward these dark corners of the Internet? "I don't think I'm a sufferer," she laughs, "just an enthusiast."

Bennett's fervor carries over to her podcast. On The C-Word, she and Dunham plumb the exploits of complicated women who, at one point or another, society has labeled "crazy." Subjects include Judy Garland, socialite-turned-plastic-surgery-curiosity Jocelyn Wildenstein, Mariah Carey, and notorious Blade Runner star Sean Young. Each episode is a researched, detailed dive that also comes teeming with innuendo. (The hosts offer disclaimers when their fascination leads them into conjecture or myth.) "I'm not necessarily against publishing things that are maybe untrue?" Bennett says with a shrug. "I mean, I think [journalists] should not, but the guy who publishes my zines, I told him, 'I want to publish rumors and gossip,' and I asked if he was afraid of any potential legal ramifications and he said 'If anyone sends me any kind of cease and desist letter I'm just going to email them a picture of Charles Manson.'" Still, each story—in the zines as well as on the podcast—presents a certain redemptive analysis of its subject. "When I make the decision to write about someone it's because there's something about them that feels familiar," Bennett explains. "The writing is the way in which I figure out that familiarity and where it lies. I'm very attracted to people who live relatively normal lives and then things turn just a couple of degrees off, and they start to make this radical series of decisions that propels them into infamy. It's because I can see myself doing these things: If things were a little different, that could be me. I think when someone falls in love with a crime they fall in love with a crime because they can imagine doing it."

In our current social climate, cancel culture looms like an ever-circling albatross—something Dunham knows all too well. This just makes Bennett's approach feel radically humanizing. "Downfalls are built into success stories because in America we have a bifurcated pleasure," she points out. "One pleasure is watching the ascent and enjoying the cultural material that comes from that, and the other is watching someone fucking self-destruct. It triggers some squalor fascination where we're very interested in squeezing the last drops of entertainment from the body, even if it's bad."
When Bennett first moved to New York City in 1996, she became a model, landing i-D covers and walking for Hussein Chalayan and Stephen Sprouse. She remembers feeling competitive, conjuring up Craig McDean photos of herself next to another girl with exquisite, Greta Garbo-like features on her phone. "This was my rival," she says of the Garbo girl. "She was just a little more special than I was."
Bennett has since been married and divorced, twice, to the artist Banks Violette. Now she's in a new relationship (with artist Leigh Ledare) and raising a 9-year-old son. When she's not writing and podcasting, Bennett spends much of her time working behind the scenes in the art world. In addition to showcasing artists like Matthew Barney, Richard Prince, Roe Ethridge, Anicka Yi, Anne Collier, Carroll Dunham, and Violette through Gladstone, Bennett has collaborated with Aida Ruilova, Sue de Beer, and Bjarne Melgaarde. ("Bjarne is the purest collaboration because he allowed me inside his work in a way nobody else ever did," she says.) The podcast has brought her a new wave of interest. Is it weird to be on the receiving end of attention once more?
"I've thought a lot about the corrosive qualities of attention in relation to other people's lives," Bennett tells me, eyes searching the blue-lit Algonquin room. "I've thought about it with artists, and then I've thought about it with tragic celebrities I'm obsessed with. I'm not an incredibly successful person so let's immediately frame this by saying I am very much a niche, subcultural interest until I write my Lifetime film." She sighs, kidding and not kidding. "When I was a model, I knew what it was like to do your best and for someone to say no. It's a stream of no's. And I thought, I'm not doing that to myself ever again. So I've been very passive and somehow things have just sort of come to me. I feel like a sleepwalker. You just close your eyes and go."

Patrik Sandberg is a writer, editor, and creative director in New York City. He co-hosts the podcast Not Really.