Isn’t It Funny? HALEY KALIL’S Unscripted Story

Photographer DRAKE HACKNEY @drakehackney
Stylist ZOE GOFMAN @zoegofman
Hair RUSLAN NUREEV @hairbyruslan
Makeup VANESSA MURO @vanessamuro_
Intern MADELEINE POEL @madeleine.m.p
Stylist Assistant CASSIDY WRIGHT @cassidywriight
Location AGENCY STUDIOS @agencystudios

Words by Delayne Willet

Haley Kalil has crafted her dream career from the concept of a fake boyfriend, inspired by her experiences with semi-fabricated real men while living in New York City. With over 20 million followers on Instagram and TikTok, her presence, characterized by auburn hair and a radiant smile, is ubiquitous across social media. Known as Haleyy Baylee, the comedian has established an empire doing what she loves most, making runways, red carpets, and front-row appearances commonplace. Despite growing up in rural Minnesota, far from the glamorous life she leads now, she prefers spending her days in her bespoke apartment, tripod set up, making her loved ones laugh.

Kalil sits in the ivory-toned kitchen of her Soho apartment—a place she credits with building her career. Her loosely secured topknot hangs from her crown, and her black pullover leaves only her fingertips exposed, which she uses to gesture intentionally and often. She is relaxed, expressive, and eloquent. Kalil is the epitome of an embodied woman, though she humbly denies it, serving as a fit and inspiring role model for young girls growing up online. Business owner, entertainer, comedian, model, and bioscientist are mere titles on Kalil’s resume, one that prompts some mental math to grasp how she’s accomplished so much by age 32. Having proven herself repeatedly, the savant is now ready to tackle Hollywood. The Sports Illustrated alumna and brain behind the popular “Billionaire Boyfriend” sat down with BASIC to uncover the charisma behind her character and the magic of Hayleyy Baylee.

In over three decades, you’ve lived many lifetimes and became accustomed to unexpected turns in your path. Did you ever imagine you’d be where you are now at this point in your life?

For me, this was all out of the blue. I grew up as the daughter of two engineers. My parents are very smart and were very focused on school. I’m a middle child with an older sister and younger brother. My sister is a lawyer and my brother is an industrial engineer. I went to school for biomedical sciences and psychology, with a minor in chemistry. Growing up, though, I was particularly interested in Saturday Night Live. I thought it was the coolest thing in the world that an adult could do that for a living. I remember asking my mom if I could be a stand-up comedian, but she said no, and that was the end of that story. Throughout high school and college, I focused on getting my resume ready for medical school. My best friend, whom I’ve been friends with since kindergarten, is a pediatrician. We were on the exact same path until she went to med school after graduation and I got married at 21.

As a med-school bound wife working in a Minnesotan bridal shop, what led you to the centerfold of Sports Illustrated?

During the time we were about to move to Charlotte—my husband had signed a new contract with the Panthers—Sports Illustrated held its first-ever open casting call on Instagram. I had always wanted to be a model but faced many rejections in Minnesota. With nothing to lose, I posted a video to my 400 followers, and Sports Illustrated ended up seeing it. While packing up my house for the move to Charlotte, I got a DM from the Sports Illustrated account inviting me to New York for a casting. My life changed dramatically. I went to New York with my stepmom and went through the entire process. I had never done a casting before, didn’t have an agent, and had never modeled. The entire competition lasted a year, and I ended up co-winning with Camille Kostek. That started my modeling career, going back and forth from Charlotte to New York with my husband.

How did being in the spotlight change your personal life?

After my husband finished playing, he was ready to start a family. I was not. We were best friends who got married young and realized we both loved and respected each other, so we got a divorce. We worked on ways to remain friends, and that’s exactly what we did. He’s now married with a baby and lives a very private life, unlike me. We’re very proud of each other. It worked out beautifully. I moved to New York permanently and began modeling. As we know, the industry is tough and very hard on your mental health. I was never someone who prioritized my looks, nor did anyone else emphasize them. Growing up, school was everything to me, not looks, and that took a toll. I fell into an eating disorder mindset, losing weight quickly, and went to extreme measures to cure my skin, which has never been the best. I was treating my body disrespectfully. I decided I wanted to move home, live with my family, and get a job in medicine. With two weeks left on the lease for the apartment my ex and I shared—one I couldn’t afford without him—Caleb Simpson asked to tour it. It felt like fate, or a God thing, the universe. That was in October 2022. Within five hours, the apartment tour had 55 million views. I remember sitting there thinking, oh my gosh, my stuff is in boxes, I’m ready to move home, I can’t afford this place, and now this is the only thing I’m known for! I bet on myself, signed the lease for another year, and started making content five times a day, every day, like my life depended on it—because it did. I really needed to turn this into a career. Within a couple of months, I could afford my apartment, and this became my full-time job. I’ve been doing it ever since and love it more than anything I’ve ever done.

The influencer and content creator space arguably exploded during the pandemic, creating an industry that didn’t exist in this way before. Did you have any desire to start creating content or get into the “influencing” space before your big break?

I spent COVID watching TikTok. I didn’t really post much, and when I did, it was as a model. My content was very different. It was just me being, I guess, pretty? That feels weird to say. I definitely don’t post like that anymore; it’s so out of character. I was just trying to do well at my modeling job and sacrificed who I was to do that, which took a toll on my mental health. The apartment tour happened in October 2022, and that’s what encouraged me to make a YouTube channel. That’s when I started posting comedy. I was later than the 2020 content creation spark. I never saw myself going into the world of influencing, nor do I consider myself an influencer. I am a content creator. I create comedy content. If I can give recommendations for the hair products I like or the makeup I use, I love if that influences someone because I want to support the products and share them internet-wide group chat. My mom never let me be a stand-up comedian, so this was the only way to do it. I wasn’t going to be on SNL, but I could make my own. Also, I was 29, which is a lot older than most people when they start. I thought, if there’s ever a way to get into doing comedy the way I want to, this is going to be my only and fastest medium to reach people. I was excited to start because I felt so boxed in by modeling that I was exploding with ideas.

You mention wrapping the harder-to-swallow parts of your messaging in the sweeter package of humor. While your content is fun, do you also use it to communicate a larger social commentary to your audience?

My whole life, growing up as a nerd, I was never one of the cool kids. I had to be funny for people to care, and I also used humor to cope. My whole family is very logical and unemotional, so one of the ways we cope with the harder things in life is through humor. For me, humor was always a way to express myself. I always felt like a message is better received when it’s funny. Growing up, I connected with creators like Jenna Marbles because she delivered her messages wrapped in comedy. Subconsciously, I began doing that—not even as a way to reach new people, but because it was my best way to communicate my feelings and the things I was going through.

Since this outlet can be a form of catharsis for you and encompasses much of your career, do you find it difficult to be trans- parent with your followers? How do you balance honesty with privacy?

I was making a video about this today. As a comedy creator, you don’t talk about your life as much. You have an audience where you feel like you know them, and they feel like they know you, but they know very little about you. People can tell if I’m going through things in my relationship because I’ll start posting comedy about it. People knew when I broke up with my ex because there was a sketch I did about that. It’s the easiest way for me to talk about the things I go through without it being heavy. There’s too much heaviness out there. I don’t want to trauma dump. I’d rather make people chuckle and, if they’re going through the same thing, help them understand. Being perceived is hard, especially by strangers. A world of strangers is even harder. People will take one look at you and put you in a box. I get it. I do the same thing. More than anything, this career has taught me to have a little more patience with people and a little more openness. A lot of people are not the way you initially judge them to be.

Do the characters you play ever mix with your real personality?

That was a learning curve for me. I wanted solely to play a character, but very soon it became clear that people thought I was the character I played. You get into murky waters because you assume people know who you are, but unless you’re telling them exactly who you are, how would they ever have a chance to know? Certain things you say can be perceived in so many different ways. I try now to show people who I am because the hardest part of perception is feeling misunderstood and not knowing how to communicate that. Once you hurt somebody’s feelings, the last thing they want to hear is how misunderstood you feel. That’s tone-deaf and awful. The things that I’ve been able to do because of my career are thanks to all the people who watch me and hit follow. I would not be here, even if I put in all this hard work, without the people who have supported me. Baseline, I owe them the world, and I want them to know the type of person they’re supporting. I want to be the type of person that people want to support.

You didn’t grow up with a focus on a career in entertainment. Now that you’ve developed this launchpad and a loyal fanbase, where do you want to take things?

All of this happened by chance. Some people use content as a jumping-off point to write a book or be in movies. All I wanted to do as a kid was be a comedy actor. I love what I do. I love filming stupid little videos around my apartment with my friends and family. If you spend a day with me, you’ll see me running around with my tripod, filming the wackiest stuff. It brings me so much joy. I can’t take days off because I genuinely enjoy it. I obviously want to see where it can lead. Now, it’s about saying yes to things that pop up. We’re working on a digital short show, but I can’t say much about it. I have so many ideas I’d like to integrate. Many celebrities have the backstory I have. They never realized they would be successful, doubted themselves, and it happened almost by chance because other people believed in them. I would love to show how real and down-to-earth so many of these people are. We never get to see it due to PR and media training. There’s something so valuable in raw and honest conversation. I would love to show that side of Hollywood. I never got to see it growing up, and the only reason I do now is because I’m stepping into that world. I’m here trying to do the best I can with my platform. I want to make it as entertaining and fun for everyone as possible. I’m exploring many different mediums right now, outside of social media.

“There’s something so valuable in raw and honest conversation. I would love to show that side of Hollywood. I never got to see it growing up, and the only reason I do now is because I’m stepping into that world. I’m here trying to do the best I can with my platform. I want to make it as entertaining and fun for everyone as possible.”

Knowing what you’ve accomplished in the social media space, I can only imagine the ripple effect you could inspire on a large scale. What would you like to see more of in the film industry?

Gen Alpha and Gen Z would love to see more of the people they see on their phones every day in the movies and TV shows they watch. Growing up, my beef with Hollywood was that it seemed like only the sons and daughters of people in Hollywood or trust fund kids ever broke through. It was such a guarded community that, growing up in Minnesota and not knowing anyone in the industry, I felt there was no possible way I’d ever be accepted into it. Nowadays, with content, you have creative minds from around the world. All you need is a phone. You now have an entire group of people who were once ostracized from Hollywood and who have so much creativity at their fingertips. I think we’ll see a huge upswing in the innovation of movies, art direction, and television. Obviously, Hollywood is the last to change, and they are still pushing back to this day. We are about to see incredible diversity in entertainment because talent doesn’t just belong to the classic Hollywood trope of the white upper-middle class.

Even in the three years you’ve been exposed to a larger audience, the landscape of media and access to it has shifted dramatically. Throughout your career, have you experienced a dark side to such reach?

I feel bad for the younger kids. It’s so overstimulating. Everything is at their fingertips: lies, truths, who knows. But I also think Gen Alpha is really good at decoding that stuff because they’ve had it in their faces their whole live. I do think it’s going to be really, really important to be a strong parent or mentor in this day and age to communicate to kids that they’re so much more than what they see online. I’m so lucky that my mom and dad are incredible. I sing their praises. They instilled in me the value of hard work and that what you look like, the money you make, and your worldly success mean nothing. It’s how you treat people that matters. Social media platforms also must take charge to create a safe place for kids. To protect this community, it will fall on the platforms and—unfortunately—the children themselves to cultivate safety and security. And creators. I have a lot of young followers and I know that, which is why I don’t swear. It’s not just because I want to be brand- safe, though that’s a perk. I get a lot of ten or 12-year-olds running up to me on the street, and the last thing I’d want is to think, oh my God, they saw that one video, or that I might have taught them a word they didn’t know. I try to be very responsible with that. You wake up at 30 and you suddenly understand. I’m way more patient now. We’ve all messed up so many times and we’ve all judged people. That knowing comes with age. I’m so grateful I started this at 29. If I had started at 18, I probably would be very different. My digital footprint is cringe, and I’m okay with it. It’s self-aware.

BUY ISSUE 27