THE MEN OF HULU’S NEXT HIT ‘HOW TO DIE ALONE’ TALK SYNCHRONICITY, SAFE SPACES + THIS 'VERY SPECIAL' SHOW!
IN CONVERSATION WITH:
COREY GUEVARRA, EDITOR IN CHIEF
PHOTOGRAPHY: THE TYLER TWINS
(COURTESY OF DISNEY)
Ah autumn, leaves are aging, weather’s changing & perhaps most importantly; fresh fall TV arriving :-) -Of this year’s roster, 1 new show in particular delivers ALL of the things we only hope for from our televised seasonal selects. If you ask any viewer of Insecure or White Lotus who their favorite breakout star was, you’ll almost unanimously receive Natasha Rothwell praise. Cut to 2024 & she’s set to front run her very own series, the equal parts hilarious AND heartfelt ‘How to Die Alone’! Although Natasha wore a myriad of hats (both in front & behind the camera) the cast’s entire ensemble perfectly weave the show together in a complimenting tapestry of comedy, drama, relatability & poignant self reflection.
Of the male leads, ‘How to Die Alone’ also did not disappoint, casting aboundingly equipped actors, immediately believable as the only possible choices to breathe life into their roles. Jocko Sims, KeiLyn Durrel Jones & Conrad Ricamora bring an almost bespoke tailoring to their characters in a way that above all else makes you believe every point & punchline that escapes their lips. In our very first 3-person interview we got a chance to catch up with these talented titans, chatting everything from synchronicity, secret beat making skills & the excellence of this show filled “so much heart”….In their own words, here are the men of Hulu’s next hot-hit, ‘How to Die Alone’.
IT’S 7AM ON THE WEST COAST GUYS, SO I HOPE EVERYONE’S OUT EAST [LOL] -JUST FINISHED [MOST OF] THE SEASON & FIRST LET ME SAY BRAVO! IT'S A TRULY GREAT WATCH! THE SHOW IS SET IN NYC, BUT WHERE IS EVERYONE FROM ORIGINALLY?
Jocko: Wow, thank you! This is actually of the 1st bit of feedback I’m getting to hear about the show. So very grateful/happy to hear that you actually enjoyed watching it! ….Also, I guess I can start? [lol] -I’m originally from Texas, grew up in both San Antonio & Houston. My mom eventually moved to Los Angeles & after I got the acting bug, I moved out there as well, studied & got my BA in Theater from UCLA. -My original life aspiration was to become a doctor believe it or not, but after I went to my first audition & booked it, I KNEW this is what I was supposed to do with my life!!
KeiLyn: I was born in Denver, but I claim Maryland because that’s where I really grew up. I’m a "military brat" & my dad is from Maryland, so we moved there when I was about 3 or 4. That’s where I spent most of my formative years. I tried moving to LA a few times in my late teens & early twenties, but something always seemed to pull me back east. Eventually, I ended up at NYU for grad school in 2012 & I’ve been in New York ever since!
Conrad: My story goes west to east with a bit of Denver & a military upbringing mixed in -much like KeiLyn!! I was born in Santa Maria, California while my dad was stationed in the Air Force, but we moved away before I even turned 2. The first decade of my life was a whirlwind of locations—Denver, Colorado, Reykjavik, Iceland & various spots in Florida. By middle through high school, we settled in a small town just south of Alabama called Niceville, Florida. -I’m sure you can imagine what growing up was like for a little gay Asian boy navigating the south.
WHEW. BUT THAT IS ALSO SUCH A TESTAMENT TO YOU GRABBING THE REIGNS OF YOUR LIFE CONRAD. IN FACT, ALL OF YOU INCREDIBLE GENTS, LOOK @ WHERE YOU ARE NOW! JOCKO YOU TOUCHED ON IT A BIT, BUT HOW DID EACH OF YOU ACTUALLY END UP IN ACTING?
Jocko: You know, I was always smart in school. Like I knew I COULD be a doctor, but as soon as I got to college I was like, “I need some artistic stuff”. Growing up I was always making music or dancing but only really allowed myself to view it as a hobby. My mom did try to encourage me however. She did try to nurture my creativity, always telling me that I should take some sort of class; band, theater, something. -I never took anything. -Then I got to college & turns out she was right all along [ha].
KeiLyn: I have to give a lot of credit to my pop. He was a single dad raising my 2 older brothers & I. He’s not an artist himself, but he’s an incredibly handsome, charismatic guy, naturally outgoing & funny & often drew inspiration from comedians like Richard Pryor & Eddie Murphy. Whatever he was watching, we were watching too & his taste in humor definitely influenced me.
From a young age, I knew I wanted to be the funny guy, the clown. I was deeply inspired by Jim Carrey, Martin Lawrence, Eddie Murphy & Will Smith. The original Bad Boys movie, in particular, had a huge impact on me. Growing up in lower-middle-class Maryland, I didn’t know how to break into Hollywood, so I took the theater route. I spent over a decade studying theater & fell in love with that side of acting. I came to realize that many of my favorite actors—like Denzel Washington, Meryl Streep & Angela Bassett—were all theatrically trained. My journey has been shaped by both my love for black comedy and my dedication to the theater.
Conrad: My path was very, very circuitous -not direct at all lol. I didn't even start acting until I was 22 -& growing up on Air Force bases, there weren’t any arts outlets at all. As a kid, I’d sing & dance with friends, making up routines to Mary J. Blige & SWV, but once I hit middle school, the culture shifted. I was a small kid surrounded by older guys with like full beards & I unfortunately got bullied for being expressive. So instead, I dove into competitive tennis, which led to a college tennis scholarship. It wasn’t until my junior year of school that I took an acting class & it was just to fulfill an elective- but that’s where I discovered my passion for it. I loved the electricity of performing, especially when tackling a monologue about a broken family, which resonated with me due to my own strained maternal experience. After I graduated, I started taking acting classes in Charlotte & got into community theater & eventually earned a fellowship at the Walnut Street Theater in Philadelphia. I spent about 4 years there before going to grad school at the University of Tennessee to focus on the craft & study the Alexander Technique. During my 3rd year, I auditioned for Here Lies Love in New York & landed the role before graduating. While doing that, I auditioned for How To Get Away With Murder & ended up booking the part of Oliver after initially auditioning for Wes. -So like my whole journey to Hollywood wasn’t planned at all lol—I even turned down a chance to audition for I Now Pronounce You Chuck and Larry. I was already working at the North Carolina Shakespeare Festival at the time & completely fulfilled because acting [as a craft] has always been my focus. Hollywood just sort of [eventually] came along with it lol.
SO YOU GET A SCRIPT WITH THE TITLE “HOW TO DIE ALONE”!!! -WHAT IN THE WORLD ARE YOUR VERY FIRST THOUGHTS?
KeiLyn: When I first saw the email & the breakdown saying ‘How To’, at first I thought it might be a spin-off or something similar to How To Lose a Guy in 10 Days. I didn’t get the script until after I’d already booked the role, so I had to rely on the sides & any information I could gather. [Also, funny enough, I didn’t audition for Terrance until much later—I’d initially auditioned for Alex].
I wasn’t sure what to expect from the title, even thinking it might be a procedural trying to capitalize on the success of How To Get Away With Murder. Then when I saw Natasha’s name & read the sides, it REALLY hooked my attention. Without disparaging anyone else [of course] Natasha was my favorite part of Insecure, I was immediately excited to see her do her thing!
[I MEAN YOUR CO-STAR WAS IN FACT ON ONE OF THOSE PREVIOUS ‘HOW TO’ SHOWS, SO YOU WERE DEFINITELY ADJACENT KEILYN]
Jocko: I actually have a funny story about how I came across the script for this project personally. I don’t remember my exact reaction when I first saw the title, but I do rememberer my manager, who ordinary would never, tell me she read the entire script before I had the chance to. It left her laughing so hard that she insisted I had to read it immediately! That day I literally happened to be at JFK (of all places/airports) getting ready to board a flight. I pulled out the script & was legitimately laughing out loud on the plane! -It was one of the funniest pilots I’d EVER read. When I landed in LA, I told my manager, "I’m all in on this—whatever it takes, let’s make it happen."
[WOW. YOU HONESTLY COULD’VE BEEN ANYWHERE IN THE WORLD WHEN YOU DECIDED TO HAVE A LOOK AT THE WORK, BUT JFK FOR A STORY HEAVILY BASED AT JFK IS NEXT LEVEL SERENDIPITOUS JOCKO.]
Conrad: I’m a big journaler & [the book] The Artist's Way really got me into the habit of doing what they call “mind dumps” in the morning—just writing out all my thoughts. One recurring theme in my journaling has been telling stories about people who are searching for love or who are already in love but keep facing obstacles. Despite everything, they remain hopeful & keep believing in love.
When I read this show’s script, it struck me as the perfect embodiment of that idea. It’s about self-discovery & healing, which resonates deeply with me. I truly believe in RuPaul’s infamous line: “If you don't love yourself, how the hell are you gonna love anybody else?” There’s a lot of depth to that statement, but at it's core, it’s undeniably true. And to me, this show captures that essence beautifully.
THE SHOW WILL BE ABOUT TO PREMIERE AS THIS COVER STORY COMES OUT, BUT A PART OF THE MAGIC OF STREAMING IS THAT PEOPLE CAN DISCOVER THIS SHOW FOR THE FIRST TIME ALMOST ENDLESSLY. FOR ANY NEW VIEWERS, PLEASE TELL US ABOUT EACH OF YOUR CHARACTERS IN 'HOW TO DIE ALONE':
Jocko: So I play Alex who’s the current boss & former fling of Mel & now he’s about to get married. The dynamic between Alex & Mel is really intriguing because they once had a strong connection that didn’t quite work out. One of my favorite moments is when Alex awkwardly has to tell Mel that he’s getting married & wonders if she received the invitation. Initially, Alex seems to be in control, but when he learns that Mel has RSVP'd and is bringing a date, he’s completely thrown off. He starts fumbling, saying things like, “I have a date. You have a date? That’s great. We both have dates. Of course, I have a date. I’m getting married. What are we, a calendar?” It’s such a funny, real-life moment that captures the awkwardness of dealing with someone from your past. Natasha & the writers have done a fantastic job balancing the power dynamics between these two characters.
[YEAH, I MEAN, YOU GUYS WOULD BE AN HR NIGHTMARE IN REAL LIFE-LOL]
Jocko: You know, I’m sure this probably happens all the time, but we should definitely toy with that a little bit more next season. Add some HR drama in there.[ha]
KeiLyn: Terrance is an Air Force vet so he's seen some of the world. Albeit on the military's dime, he genuinely has a thirst for adventure. He seems like a very responsible guy, very emotionally mature. He wants to encourage people around him, especially people that he has an affinity for, like Mel (& probably Shaun & Deshawn on their off moments) to evolve & to grow & to step out of all the cliches & comfort zones. I feel like he reads a lot of self-help books & he just wants to live a full life instead of just existing -he encourages Mel to do the same.
[WOW THERE ARE THOSE PARALLELS AGAIN; YOU AND YOUR COSTARS ARE ACTUAL AIR FORCE KIDS, RIGHT?]
KeiLyn: Yes I affectionally refer to it as being an Air Force brat [lol]. My parents were in the Air Force. My brothers are in the Air Force. Natasha’s an Air Force kid, Conrad is an Air Force kid!
[THE SYNCHRONICITIES & THE UNIVERSE PULLING YOU ALL TOGETHER FOR THIS ARE UNDENIABLE]
Conrad: Truly!!! ….So Rory…. Rory is “wonderfully messy” which honestly has been a refreshing change after playing Oliver for 6 years—someone who was always so put together, anxious & overthinking everything. When I first auditioned for Rory, I really let loose. I painted my nails & embraced some of the things I’d wanted to try in my own life, just living out loud, unapologetically. Rory embodies that kind of freedom, though maybe a bit too loudly & for a bit too long [lol]. In the first episode, Rory finds interest in someone & starts grappling with the idea of getting their life together. I do love that Rory is messy at their core, but is also resisting conformity. They’ve always pushed against traditional norms (like monogamy) but then start to wonder if maybe they’re not entirely who they think they even are. -It’s a great dynamic to explore.
[RORY IS SO COMPLICATED CONRAD, YOU’RE LOVING THEM, THEN YOU’RE UPSET WITH THEM. EVERYONE’S CHARACTERS ARE SO MULTI-LAYERED.]
WHAT MAKES YOU GUYS SAY YES TO ROLES? (LIKE BESIDES YOUR RENT OR MORTGAGE OF COURSE LOL)
Jocko: What made me say yes to THIS role was undoubtedly that I’m a big fan of Natasha. People often mention White Lotus & Insecure first, but I have to shout out Sonic the Hedgehog—she was hilarious in that! It’s a deep cut!
When I’m considering scripts or roles, I look for things that genuinely entertain me. It might sound a bit mundane, but I try not to choose projects just because it’s a job or because I want to live in a particular city. I want to be part of something I’d actually watch. After spending 20 years in straight drama, coming off New Amsterdam, I was eager to dive into comedy and have that sort of experience on set. I wanted that struggle to get lines out because we’re laughing so hard—that’s when it’s REALLY funny. So, I reached out to a few studios, hoping to land a comedy. I was thrilled when this project came along—it was like the universe delivered exactly what I’d hoped for. It came at the perfect time & I’m excited to be in something that brings this kind of joy & laughter.
KeiLyn: Personally, I have to appreciate the heart of the writing. I mean, it's a collaborative medium, but at the end of the day, there's nothing to collaborate upon if the writing's not there. -We can improv all day, but there's still got to be a structure. So I’m attracted to writing always & similarly I too like a challenge. I do enjoy playing villains & complex characters, but sometimes, like with Terrance, everything just clicks perfectly. Terrance was like slipping into a comfy pair of fur-lined slippers—everything about his story just fit so well. I see a lot of parallels between myself & this character & it feels like a natural fit. To top it off, I got to work with incredible people which is a huge bonus. Being around such talented actors not only allows me to stretch my own skills but also to learn from the best. When Something like this comes across your desk, you CAN'T say no.
Conrad: For me, it has to be something that is exciting. Believe it or not, Natasha was on my vision board after watching Insecure & Love,Simon. After seeing her 1st season of White Lotus, I was like, ohh, this is somebody who has shown us just 5% of what they can do! -I look to work with creators who are pushing not only the boundaries of themselves, but who are also honest storytellers that tap into things that move me. -Natasha has always moved me on screen, whether she’s made me laugh or cry. -If I’ve enjoyed something created by someone I admire, I want to work with them.
WHAT IS EACH OF YOUR OWN DREAM ROLE/CHARACTER?
KeiLyn: This is a tough question because if it's your dream role, it probably hasn’t been done yet. You can only think about roles that haven’t been played. For example, I’d love a role similar to a dark horse anti-hero with a heart of gold, like Matthew McConaughey’s character in the first season of True Detective.
Jocko: Not to just directly steal from you KeiLyn [lol]- but lately, I’ve been really interested in playing a police detective in a drama. I’ve been watching way too much Dateline NBC—probably at least 1 episode a day for the past few months. My YouTube algorithm is now full of interrogation videos & I find that process absolutely fascinating. So, I’d love to play a detective. On the other hand, I’d also be excited to star in a horror movie, maybe even as the killer. Both roles—the detective or the villain—seem like they’d be a lot of fun to dive into.
Conrad: I feel like my dream roles keep coming true because they’re being written by people I admire so much. Right now, I feel like I’m living my dream with being in O Mary [On Broadway] & having How to Die Alone about to be released. It feels like an embarrassment of riches, especially since these are the kinds of roles I’ve always wanted to do. I studied classical theater while earning my MFA in acting, so I’d love to tackle roles from Tennessee Williams, like The Glass Menagerie or A Streetcar Named Desire. For Shakespeare, I’ve always wanted to play Iago and Othello. -I also really love Oscar Wilde’s work. I think theater, particularly Broadway, still has a long way to go in terms of including people of color in these classic roles. But I’d be eager to take part in that progress.
WHEN NOT ACTING WHAT CAN WE FIND YOU GUYS DOING?
Jocko: I love cooking [and I would mention working out, but I’ll be out for at least six months from upper body exercises due to a gym injury]. I also really enjoy going for bike rides around the city here in New York.
ARE THERE ANY HIDDEN HOBBIES OR PASTIMES THAT MIGHT [REALLY] SURPRISE PEOPLE?
Jocko: I haven't done it in a long time, but… I used to make beats & rap actually!
THERE IT IS!!! [LOL]
Jocko: I’ve never put anything out. So people might be surprised if they read this or if I ever release anything one day.
IT'S ON A HARD DRIVE SOMEWHERE, RIGHT? MAYBE ONE DAY WE’LL GET TO EXPERIENCE SOME MC JOCKO [HA].
KeiLyn: Honestly, If I'm not acting, I'm thinking about acting & dreaming about acting. I read books for inspiration that might turn into movies, dive into plays & I do a bit of writing & directing as well. Outside of industry-related thoughts, which are rare, I enjoy working out as well & staying active. I also love spending time with my nieces & nephews—I’ve been an uncle since I was 11. Cooking & cleaning are actually pretty cathartic to me. I don’t make anything too exotic, but I'm a damn good cook. I've made a lot of women fall in love with me with my culinary skills! -I also consider myself a bit of a tequila aficionado, and fun fact: my birthday falls on National Tequila Day!!
Conrad: When I’m not working, I still play tennis. My husband & I enjoy playing at the Central Park courts, which are just a short distance from where we live. Central Park itself feels like a miracle, so I consider it a real privilege to have access to its 26 tennis courts every day. We’re both big tennis fans—in fact the US Open is playing on the screen behind me (on mute of course) -lol.
YOU’VE WORKED TOGETHER FOR MONTHS ON THIS PROJECT… DO EITHER OF YOU HAVE A QUESTION YOU’VE ALWAYS WANTED TO ASK THE OTHER?
Jocko: Hilarious, I was literally just thinking to myself how cool it would be if we were all interviewing each other lol!
Conrad: I would want to know where you guys would ideally want your characters to end up professionally & personally at like the end. I always think it's so interesting to ask your co-stars about their character’s fairytale (or not-so fairytale) ending.
[OH, THAT’S A GREAT QUESTION CONRAD!]
KeiLyn: I can’t think of any actual questions off the top of my head, but recently, I watched the last few episodes of the series & saw some of the scenes with Natasha & others that I hadn’t seen before. I was really impressed. Like Jocko as the lead, I knew he was talented, but I was still blown away by his performance. I picked up the phone right away & let him know how incredible I thought it was. So, if anything, I gotta give flowers publicly!!
[KEILYN IT REALLY IS SO IMPORTANT THAT WHEN YOU SEE PEOPLE DOING INCREDIBLE THINGS THAT YOU SAY IT TO THEM OUT LOUD!]
Jocko: Oh man, I genuinely appreciate that! I think that was about episode 7 right? -It’s funny because, even months into filming, you don't always get to work with everyone right away. Like KeiLyn & I didn’t share scenes initially, so I only had an idea of how talented some of my co-stars were. But once we finally had scenes together, especially centered around Alex, Terrance & Mel, I was blown away. Watching them bring such depth to their performances, especially in those moments of emotional intensity was incredible. Natasha & I would often glance at each other off-camera, really impressed with how you conveyed Alex’s internal struggle KeiLyn!!
[OMG, WHO IS CUTTING ONIONS IN HERE GUYS?! HA]
IN YOUR OWN WORDS, WHY SHOULD EVERYONE WATCH THIS SHOW?
KeiLyn: Not to sound cliché, but this show really just has so much heart & literally offers something for everyone! Even if you’re not a [plus sized] black woman working at JFK with a rocky life, you can STILL relate to Mel’s journey. As a whole, the show touches on real-life, universal, human experiences. Above all, it’s a feel-good show. It’s relatable, it might make you cry a bit, but you’ll definitely laugh a lot! I think we all need that right now!
Jocko: I agree. I feel like the show makes you want to be Mel’s friend, while also reminding you to check in on your own friends irl! Mel’s character really draws you in, she shows both the fun & struggle of her life -often happening simultaneously. We see her appearing to have a great time at work, but behind the veil we realize she doesn’t have it all together & deeply needs a reset. -This can be painful to both admit & of course work through. The show balances comedy with realness effectively. The humor pulls you in, but as you dig deeper, you discover layers that remind you of the importance of checking on both yourself & your people!
Conrad: Agreed! This show is exactly the dose of joy, optimism & hope we all need. After recently watching the DNC & feeling like “hope” is making a comeback, it’s refreshing to feel that same sense of optimism in the current climate. This show is the perfect boost of joy & positivity that we all need to continue to tap into right now.
FINALLY GUYS, OUR STAPLE QUESTION THAT WE'VE ASKED EVERY SINGLE 26 MAGAZINE STAR. EVERY ANSWER HAS BEEN SO FASCINATING. GENTLEMAN, IF YOU WILL, WHAT IS YOUR DEFINITION OF LUXURY?
Jocko: Years ago in LA, I had a college acting teacher explain to me how crucial it was to love where you live. He wasn’t referring to luxury per se but to the importance of having a peaceful retreat no matter how modest it might be. He said this with the context of LA in mind, where you might face long drives or crazy parking as you’re running around for auditions & such. -After dealing with all of the events of the day, it’s most important to have a calm, serene place to go back to. To me, true luxury is having that sense of peace in your home, wherever you are.
KeiLyn: I love that perspective! For me, luxury is compassion. In a place like New York, where interactions can be brusque—whether someone bumps into you or is curt at the grocery store—it’s easy to forget that everyone is dealing with their own stuff. I always remind myself that someone might be having a rough day, they might be going through a breakup or a personal loss & is subsequently filtering everything through that lens. Having compassion, especially in those moments, is the true luxury to me. Moving through the world with a deep sense of understanding for others, even if you don’t always receive it in return. Even if you start your day with a full heart, you might not always encounter the same kindness. So, when you do give (& also experience it), it feels like a rare, very valuable, luxury.
Conrad: I’d have to say that time is the ultimate luxury for me. But it’s not just about having time—it’s about purposely spending it on things you love. Whether it’s work you’re passionate about, relaxing, or simply just being around the people you care about, it’s all about making that time truly count. It might sound cliché, but time really is limited & it can’t be bought, it’s the ultimate currency. So being intentional about how you use it, makes all the difference. It’s the truest luxury.
