“I’m not a fairytale,” writes Caroline Calloway early in her long-awaited memoir, Scammer. “But I’m not a criminal either. I’m a writer.” By now Calloway is pure online folklore, a person we’ve heard about almost entirely second-hand. She’s been a fairytale, a criminal, an influencer, a party girl, a visionary and, of course, as most of us know her: a scammer. But, in her memoir, we finally have the definitive account of the life and times of Caroline Calloway.
To finally be able to engage with Calloway’s art is to see a very different side of her. Scammer is a delicious read – a Prozac Nation for the 2020s: parts salacious, profound, witty, harrowing. Calloway writes, “People already think there is nary but tinsel and fluff in my pretty, evil mind,” and by the close of Scammer, even the most cynical critic will be a card-carrying follower. I’m not saying Calloway is the second coming of Eve Babitz, but I’m not not saying that.
Referencing writers like Lorrie Moore and Elizabeth Wurtzel, it’s a memoir in love with its form. It sheds light on the side of Calloway we don’t know; the woman whose twenties were blighted by a destructive Adderall addiction and her father’s suicide. It is an unsparing rejoinder to her former friend Natalie Beach, who famously shivved her in her viral The Cut essay, I Was Caroline Calloway. And it is, above all, a tribute to her beloved alma mater, Cambridge, where Calloway was first noticed for her confessional Instagram posts.
This interview is – tragically – the moment I realise my laptop camera is irreparably busted, casting me in an overexposed glow. “You look like a drawing of a ghost of a Victorian orphan,” Calloway says as the call begins, and it almost kills me. Of course, she is the polar opposite; reclined elegantly on her balcony in Florida, Aperol Spritz in hand, she is living in glamorous exile. She blesses me with an introduction to Matisse, her precious Siamese cat, as he suns himself next to her.
In between trips to the post office to send out copies of Scammer, Caroline Calloway answers AnOther’s 50 Questions.
1. Where are you right now? Sarasota, Florida.
2. Can you describe the view from your balcony? Palm trees, water, a bay where there are sometimes dolphins. There’s a literal flock of flamingos nearby. It’s very camp, it’s very tropical, it’s very Florida-core.
3. What’s your favourite thing about living in Sarasota? How productive the isolation forces me to be.
4. How are you feeling today? Happy for the first time in eight years.
5. Do you enjoy doing press? I’m starting to. For a while, it was really unbearable.
6. Do you feel better understood? I think it will take time. I don’t think it’s something that can be solved in a night or a week or even a month. I think it will take having Scammer out in the world for a period of time to really feel understood.
7. What will you be doing after this interview? Going to the post office to send out the last of the Scammer galleys to reporters.
8. What are you wearing right now? I am wearing a Matilda Djerf tube top and Matilda Djerf blue pants, and comfy sneakers with fuzzy socks.
9. What did you learn from growing up in Falls Church, Virginia? That I want to leave Falls Church, Virginia.
10. Tell us a piece of Caroline Calloway lore we don’t already know. It’s a true testament to how much I poured every interesting detail about my life into Scammer that it’s so hard for me to think of anything that’s left. I meant to include this in the book but I forgot; the only time I ever thought to myself ‘is Natalie maybe a bad person?’ was this one moment.
We were talking about our favourite animals, and my favourite animal is the beluga whale because I think it looks like they’re always smiling and they’re really friendly to humans. If you drop your iPhone when you’re kayaking in a fjord in Norway, a beluga whale will dive down to retrieve your iPhone and bring it back. Natalie was like, “Oh my god, my favourite animal is a whale! I like orcas because they’re apex predators and nothing eats them, they just eat everything else”. I thought to myself, “That’s really fucking dark,” but then I was like, “No, she’s just a sweet girl!”
I never thought about it again until I found out she had been quietly hating me the entire time I’d been in love with her.
How are you feeling today? “Happy for like the first time in eight years” – Caroline Calloway
11. What qualities do you look for in a friend? I look for non-judgmental friends. I have to, because a lot of people who meet me have preconceived notions about my tar-black soul and the evil that lives inside me. I like people who are not dictated by shame, who are not influenced by how other people tell them to be or what the consequences of not agreeing with the status quo are.
12. Who would play you in the movie of your life? Emma Roberts, with Maude Apatow playing Natalie and Lena Dunham writing the script.
13. Who would you want to direct it? Also Lena Dunham? Yeah. In fact, she’s already written the script, I would just like her to direct it. I think she’s the perfect person to tackle the Caroline Calloway cinematic universe.
14. What’s your biggest vice? I drink too much.
15. What’s your biggest virtue? This hasn’t always been the case, but for the past year I have reorganised my life around a single priority, which is making books. Not just Scammer but Scammer and the books that will come after it. I think it takes a lot of dedication and chutzpah and hustle to be that single-minded and go after your dreams.
16. What do you want readers to take away from Scammer? I hope that it makes them feel less alone. That’s the reason I read and I think that’s the most beautiful thing a book can do.
17. What’s your favourite thing about the UK? Cambridge.
18. Do you have any regrets? Yes! Is that a joke? Of course I have regrets. I’ve done so many things wrong. But I think nursing regrets make for a very toxic and inhospitable interior world.
19. What’s the best thing you’ve ever read about yourself? There’s only been two reviews of Scammer so far. Rolling Stone said, and I bet I can quote this off the top of my head, “the writing itself is Swiftian – sapphic and layered and annoyingly clever, even if you try not to bob along to the tune.” And Celia Walden of The Telegraph said “I had to force myself to put Scammer down in the early hours. It’s brilliant.”
20. What’s your favourite Taylor Swift album? Ah! I’ve been waiting my whole life for someone to ask me this question during an interview. My favourite album is Midnights, actually.
21. I feel like I need to ask you what your thoughts are on the Ice Spice feature? The music listener in me … it wasn’t for me. The publicist in me was like, “Genius! 11/10! So smart.”
22. Do you have a motto in life? Where there’s a Callowill, there’s a Calloway.
23. What’s the important lesson you’ve learned? Failure isn’t failing, failure is not trying one more time. Obviously you can fail, I’m not advocating for toxic positivity here where everything is a success and you ignore reality, but failure is never permanent if you just try again.
24. Who’s the first person you show your writing to? An amazing up-and-coming writer from Cambridge. He got a Master’s at Oxford in Creative Writing and just won several fellowships to study Creative Writing at Columbia in New York. His name is William Hutton and he hasn’t released his first novel yet but someday I think it will be part of our lores that he edited my early books and that he was one of my first readers.
I also love sending my stuff to Sammy Koppelman – a Biden speech writer who went to Harvard; Mike Crumplar, a Hunter S Thompson figure who covers Dimes Square and downtown New York; and Zachary Fine, a Rhodes Scholar in Oxford.
25. What makes a good Instagram caption? Good writing.
26. If you could say one thing to 20-year-old Caroline, what would you say? I’d say, maybe think about that killer whale comment a little more … Um, they’re your favourite animal because they’re apex predators? It’s giving parasite … it’s giving uncomfortable foreshadowing.
27. Are you an early bird or a night owl? Absolute night owl. I don’t think I’ve seen what 9am looks like for several years.
28. What would you wear to the Met Gala? Turquoise and fresh flowers in my hair. A cornucopia of orchids.
29. What’s your favourite word? Every couple of months I come across a word that delights me to my marrow and I think to myself, I gotta write this word down cause someday someone is gonna ask me what my favourite word is. I can’t think of a single word I like in this moment. This always fucking happens to me. I don’t think I’ve ever read a book in my life. Words? What are words?
30. Um … what’s your least favourite word? Honestly, at this point I’m not even sure I speak English. I’m not sure how we’re having this conversation because I’m post-language. I have no opinion on words. I’ve never encountered words. I’m losing my mind trying to answer this question. I feel like a robot someone just splashed water on. I’m literally short-circuiting.
“Of course I have regrets. I’ve done so many things wrong. But I think nursing regrets make for a very toxic and inhospitable interior world” – Caroline Calloway
31. Which memoirs and writers inspired Scammer? I was really, really, really inspired by Carmen Maria Machado’s In the Dream House. It’s a very brilliantly structured book. Every chapter is her story as told through a literary trope. Obviously, I couldn’t copy that but I really spent a lot of time thinking about how you make a memoir unlike any memoir that anyone’s ever read before.
The other memoirist who really inspired me was Taylor Swift. When I went to the Eras Tour, she had thought of every little detail in order to make her fans happy, down to the light-up wristbands. I didn’t want to waste a single sentence. Oh, and Elizabeth Wurtzel, Sylvia Plath, Annie Ernaux and Tove Ditlevsen. Those six girlies together are my six favourite authors in the world and yes, I’m including Taylor Swift as an author. I’m sorry but we gave the Nobel Prize in fucking Literature to Bob Dylan not too long ago. If we’re doing that then Taylor Swift is a fucking writer, OK?
32. What’s your favourite book of all time? Scammer. I know I shouldn’t say that and there’s people who will read this and just find me insufferable, but I poured my heart and soul into that book. It’s the beginning of the rest of my life.
33. What did you learn from starring in the Nicole Kidman-starring 2007 film The Invasion? I learned that I didn’t want to be an actor. That was surprising to me at the time because I knew I wanted to be famous, and in 2007, the only way one did that as a child was to become a child actor.
34. Do you have a favourite scammer of all time? Maybe Anna Delvey.
35. What’s on your bucket list? Books that I want to make.
36. What was the last film to make you cry? Honestly, I’ve been working so hard in Florida I haven’t seen a movie in like six months.
37. Do you believe in love at first sight? No, but I’m not sure I believed in Adderall addiction until it happened to me.
38. What is the most spiritual or holy place you know? Cambridge at dawn.
39. Do you have a favourite bookshop in the world? One is the Haunted Bookshop in Cambridge; that’s what it’s called, I’m not disparaging it. Another is Three Lives & Company in the West Village. And now that I’m in Sarasota I should shout out to A. Parker’s Rare Books because if that little place shuts down I’m going to be shit out of luck.
40. Have you read the new Lorrie Moore book? No. I don’t actually know what it’s called.
41. What’s your most treasured possession? I was gonna say Matisse but he’s his own being, I would never call him a possession. He does me the honour of cohabitating with me and sharing our lives. But in the sense that if I could only save one thing from a burning building it would absolutely be Matisse.
42. How did you feel about appearing in The Cut for completely different reasons, as one of their modern ‘It’ girls? I was shocked and touched. Like, are we about to kiss, me and The Cut?
43. What are you working on? My next book. It’s called The Cambridge Captions. No one helped me make any of my content about Cambridge, I still own the full copyright, so I’m going to put them together in a book. I’m going to write caption-length stories about what was going on behind the scenes with each of the captions.
44. How often would you like to publish a book? Over the next few years I’m going to turn out books as fast as I can. I really want to get financially stable and save up as much as I can so I can pull a fucking Donna Tartt and disappear for five to six years to finally make And We Were Like.
45. Shag, marry, kill: Oxford, Cambridge, St Andrews? Kill St Andrews. Shag Oxford. Marry Cambridge – obviously.
46. What is the biggest misconception about you? That Natalie ever ghostwrote a single caption about Cambridge. It kills me when people say she was my ghostwriter because, at most, she was only ever my co-writer. No one in the public ever saw a single thing that we co-wrote together. The stuff that made me famous was me and me alone.
47. What would you say to the Caroline Calloway imitators of today? What I would say to them is honestly, thank you, everyone should be wearing fresh flowers in their hair.
48. What are you most proud of? Scammer.
49. Who is Caroline Calloway? You’ll have to read Scammer to find out.
50. Finally, did you enjoy doing this interview? Yes! I had so much fun.
Scammer by Caroline Calloway is available to pre-order now.