One of the best nights of Jimmy O. Yang’s life came after he had completely bombed a stand-up set. This was back in summer 2021, one of his first shows post-lockdown, and he was performing at the Hollywood Improv, the legendary comedy club and a stage he’s killed several times over.
For whatever reason, he was off his game. The jokes just weren’t landing. And to add to the pressure, he was running through some of the material for his follow up to 2020’s Good Deal, his debut comedy special that had, over the pandemic, become popular on ComedyTok.
“I thought I had the worst set on the planet,” Yang tells me.
He walked off the stage and tried to shake off the bad vibes. Yang still had another set to perform later that night, so he went to the bar to blow off some steam.
That’s when a vision appeared before him, wearing a backless bodysuit.
“Her back was out!” Yang tells me, with the excitement of a teenage boy. “She was wearing these green pants and I’m like, This is the hottest back I’ve ever seen.”
The owner of the hottest back that Jimmy O. Yang had ever seen turned out to be Brianne Kimmel, a venture capitalist with a portfolio worth $40 billion dollars, who just so happened to be in the audience that night. “I didn’t even want to go out,” Kimmel says, recalling the evening. “But my friends were like, No, you have to start getting back out there again.” Jimmy was entranced (“she was just as hot in the front!”) and mustered enough courage to go talk to her. They agreed to hang out.
For their first date, Kimmel booked a table at the Cara Hotel, one of her go-to spots not far from where she lived. As luck would have it, the hotel was even closer to Yang. “It was so damn close I walked there,” he says. The night led to a second date, which led to a third.
By date three, Yang said he was ready to make things official, which caught Kimmel off guard. “I thought that was so on brand for Jimmy—and so shocking for me as a girl in 2021!” Kimmel says. But Yang’s gambit worked; they’ve been dating ever since. “I just think it’s very hard to find in modern times,” she tells me. “For us, there’s never been any games.”
Overhearing her narrate the couple’s meet-cute, Yang breaks into a sheepish smile: “Hey, I know what I want!”
It’s a sunny Saturday morning when I pull up to Yang and Kimmel’s stylish Hollywood Hills home. Yang greets me at the door in a slouchy Billy Joel-Stevie Nicks concert tee, registering less like the wisecracking man-child he’s played in various roles and more like a serene dad who spends his weekends at Home Depot. He’s excited to show me the Tiki bar, an interior design project that the couple built together. Later, as I sit in front of one of those kidney-shaped pools with an elevated jacuzzi, he brings me a pot of tea, made from mint he picked out from their garden.
It’s a compelling portrait of modern domesticity: a millennial power couple who share a great aspiration to go full retiree. “Everywhere we go, we’re the youngest,” Yang says proudly.
“I mean, I’m Ukrainian,” Kimmel says, sharing a metaphor for why the pair work so well together. “I hand-make dumplings as well.”
The house has all the hallmarks of an A.D. House Tour—the airy living room, the mid-century furniture, a massive kitchen island seemingly plucked from a Nancy Meyers movie. But the centerpiece of the kitchen is a massive painting of Jimmy as Jian Yang, the clueless and diabolical Chinese app developer he played for five seasons on Silicon Valley. The painting depicts Jian Yang watching a pile of garbage burn while a godlike Erlich Bachman—the Hardy to Yang’s Laurel—looks on as an apparition in the smoke.
“That was my college,” Yang says of the HBO comedy that made him a star. “They always say, George Clooney got rejected on 17 pilots or something to that effect. Silicon Valley was my first show. How lucky was I?”
Initially, the Jian Yang character was just supposed to be a three-episode bit part on the show’s first season. But Yang proved a natural scene-stealer, adding specificity and depth to a character that seemed to have been written as a one-note joke. Soon, he became a series regular. And in the last season, he became the surprise series baddie, the final boss.
“To do the kind of comedy we were going for on Silicon Valley, the actor has to get the joke but also be able to play the drama of the scenes without ever looking like they’re trying to be funny or reaching too hard for the comedy,” Silicon Valley creator Mike Judge wrote to me in an email. “Jimmy was really great with all that, and always dialed in a subtle nuanced performance. I’m not surprised at all that he’s able to do dramatic roles.”
Post-Silicon Valley, Yang quickly proved to be an actor with range, vacillating from bread-and-butter comedy roles in films like Crazy Rich Asians to surprise turns in dead-serious thrillers like Patriot’s Day. By the time he landed a role in Space Force, the Netflix comedy series that starred legends like Steve Carrell and John Malkovick, he had grown from someone who set up punchlines to someone with a real narrative arc.
In 2021, he had his first shot as a romantic lead in Love Hard—the Cyrano de Bergerac of Netflix Christmas rom-coms—opposite Nina Dobrev. Love Hard was anything but typical, and had a somewhat tricky premise: here was a dweeby Asian guy catfishing a white woman from across the country. But the film turned out to be a huge hit. In the tradition of great rom-com parts—Julia Roberts’ scheming saboteur in My Best Friend’s Wedding, Tom Hanks’ double-crossing capitalist in You’ve Got Mail—Yang was able to transform a dubious character into someone you genuinely root for. The high degree of difficulty didn’t ever really phase Yang; through some alchemy of pathos, comedic timing, and charm, he made an online scammer almost forgivable.
In summer 2021, just as vaccines were rolling out and the world was slowly opening up again, Yang took stock of his life and went full Marie Kondo on the parts that no longer worked.
The threat of the pandemic, of living on borrowed time, was clarifying. Yang wrote an email to his agents and managers about what he wanted for the next chapter of his career.
“I want to do something that’s meaningful to me, to the community, something that’s subverting expectations,” he said in the email. “I want to kick ass in something without anybody laughing. I want to die in something without it being funny.”
A few months later, an audition for a lead role landed in Yang’s inbox for Interior Chinatown, the series adaptation of Charles Yu’s National Book Award-winning novel about the Asian-American experience, executive produced by Taika Waititi.
Yang was on the road touring, so he set up cameras in his hotel room for the screen test: “I forgot about standup and got into character for Willis Wu”—Chinatown’s protagonist.
And? “He honestly blew me away,” says Yu, who was on the video call with Waititi. “We’ve seen Jimmy be really funny. We knew that he’s very talented. But he brought a depth and an emotion to even just a Zoom read.”
Yang got the part.
“Sometimes, you’ve got to speak it into existence, even when nobody believes you at that point,” Yang tells me. “You’ve got to believe it in yourself.”
Interior Chinatown represents possibility for Jimmy O. Yang—a chance to be taken seriously, to have the sort of career-redefining role that might dictate how we look at him moving forward. To be a person of color in America is to know that while it’s nice to be liked, to be appreciated, to be laughed at, it’s even better to be understood, to be listened to, and most importantly, to have a seat at the table. “I have the ambition to do all these things,” Yang says.
Like a lot of comedians, Yang sees his standup comedy as part performance, part therapy. And unsurprisingly, his new Amazon Prime stand-up special Guess How Much? draws heavily from his relationship with Kimmel, using everything from feet hygiene to their differing love languages as material.
In the special, he also announces himself as her “sugar baby.”
“I think it took her a while to get used to it,” Yang says. “But I’m like, ‘Babe, my intention is always love, okay?’ At the end, the joke’s not on her. The joke’s really on me.”
“I’ve given keynotes at 30,000 people conferences—which is somehow not embarrassing at all,” Kimmel says. “But here, in a room of 30,000 people laughing, it’s a lot…. I love seeing Jimmy talk about his personal life because you see a lot of nods, and you might see an older couple hold hands after he says something. There’s these little moments where you’re like, ‘Oh, wow, the things that he’s saying might be embarrassing for me as a person, but a lot of people are nodding, and so we’re all on the same boat.’”
Of course, when you use your relationship as source material, it becomes fair game for gossip hounds. Recently, the Instagram account DeuxMoi—a restaurant-obsessed Perez Hilton for the Gen Z set—ran an item on the couple: “Saw Jimmy O. Yang at Mirame in Beverly Hills on Fri night. He walked by holding hands with a gorgeous blonde that towered over him. Honestly good for him lol”
Initially, the pair found the DeuxMoi post funny, sharing screenshots on their accounts. Later, they realized there was a lot to unpack there. “Once again, the joke’s on me, right?” Yang says, talking about the emasculated image of Asian men in American culture. “Oh what, I can’t go out with a tall blonde model? That’s surprising for you?”
His first comedy special Good Deal faced those kinds of issues head on. In one joke, he talks about how the work of representation never ends—not even when you’re in bed with a girl, grappling with racist stereotypes. “She was like ‘Jimmy, I’m just glad the stereotype’s not true. You don’t have a small penis.’ I’m like, bitch! You understand you just insulted my entire race of people?!”
A beat.
“But thank you.”
Yang’s cheerful demeanor is one of the keys to his comedy, which covers everything from race dynamics to microaggressions to who gets to be seen as American. He’ll play the role of the harmless, happy Asian, and then he’ll shank you with a dagger of a punchline.
“I think part of what makes his comedy unique is that he moved here from Hong Kong at the age of 13, so he has the perspective of an outsider looking at America,” Judge says. “But he’s also appreciative of the country and isn’t always looking for ways to slam it. I think he also moved here early enough to feel like he’s part of both cultures, so he can make fun of Asian culture as both an insider and outsider.”
Yang’s family emigrated from Hong Kong to Los Angeles in 2000, when he was just 13. His father was a successful businessman who thrived in the medical equipment business, while his mother (who was always “too ambitious to be just a housewife”) was the general manager of a luxury menswear boutique in Hong Kong. To move to America with dreams of better opportunities for Yang and his brother, his parents gave up successful careers and a comfortable life.
In Los Angeles, Yang’s father landed a job as a financial adviser at Merrill Lynch. But the role was commission-based and he didn’t have a network, so the family struggled financially. Growing up, Yang remembers arguments between his parents about mounting credit card debt. Two years after the move, Yang’s mother—who didn’t comfortably speak English and was unable to work—decided to take a job offer in Shanghai, resuming her successful career in retail.
That effectively broke up their nuclear family, something Yang took especially hard. After graduating with an economics degree in 2009—and following in his dad’s footsteps, landing an internship at Smith Barney—the young Jimmy O. Yang decided to try standup comedy.
“It’s a different point of view,” Yang says. “Me coming to this country when I was 13 is different from Ali Wong growing up in the Bay Area. It’s different from Ronny Chieng coming here much later in life from Malaysia and Australia, and Jo Koy being half-Filipino.”
That perspective is interesting when seen in the context of an early controversy in his career, particularly Jian Yang’s heavy fresh-off-the-boat accent on Silicon Valley. Yu remembers the first time he saw the series. “Honestly, I was like, who is this? A little bit like, woah, that’s a strong and very specific accent that he’s doing.”
On his 2020 special Good Deal, Yang said: “I don’t know what the disconnect is. Like if a white actor does a British accent, he’s a thespian. He wins an Oscar. If I do a Chinese accent, I’m automatically from the old country.”
For his part, Yang says that because he moved here as a first generation immigrant with an accent, Silicon Valley felt like playing an earlier version of himself. “I was a lost and confused immigrant like Jian Yang,” he says.
“Moving to a new place at whatever age, to whatever continent, there’s some trauma that comes with that. It’s like a part of you is gone… I don’t know how the brain works but a lot of times, I forget my memories from zero to 13. It’s like I was reborn when I was 13 in America.”
He often thinks about what he would’ve been like if the family had never moved to America: “Maybe if I was in Hong Kong, I would’ve just been happy working at Morgan Stanley.”
His mom moving home played a big role in him becoming a standup comedian. “When I was 15, 16, I didn’t have the knowledge and the faculty to understand, ‘Oh she’s a modern woman. She’s so brave,’” he says. “I think I was just like, ‘Yo, my mom left. What the fuck?’ There’s probably a bit of being lost—and a little anger even—that probably propelled me into doing standup and having the fortitude to be out every night to do that.”
You don’t have to suffer to be a poet, the poet John Ciardi once said, since adolescence is enough suffering for anyone. It’s enough suffering for comedy too. In his mother’s absence, Yang’s father demanded that the teenage Jimmy have dinner with him every night. Sometimes, hanging out at a friend’s house, Yang would decide to stay a little longer and skip dinner. His father would call. “Do you think I’m dead?” Dad would ask him. “Why do you disrespect your father like that?” In his 2018 book How to American, Yang wrote, “I was the only thread in our family that he could hang on to.”
Somehow, the emotional burden of keeping what was left of their family together fell on his shoulders. “When I was in college, all I wanted to do was go out,” Yang tells me. “But now I get it. I’m like, ‘Dude, my dad felt even worse than I did.’ I was glad I was there for him.”
Eventually, when Yang was in his twenties, his mother came back to the States. “I was still a bit headstrong,” he admits. “I still had a wall built up… But now I think as an adult, being old enough to have that empathy, really helped me heal. All I want is to be a good Asian son.”
Today, he says he has much more understanding and empathy for his parents, for what they were up against and what they had to sacrifice. “Maybe my growth was stunted a little bit because of that, but I get it,” he says. “I don’t blame him and I don’t blame my mother. It’s just how immigration works… It took me many, many years as an adult to understand her decision. It’s turned into an admiration for my mother.”
Yang and his mother have worked over the years to repair their relationship. Today they even share a dog, a “spoiled pug” named Toffee. “That dog actually helped repair everyone’s relationship,” says Yang. “My relationship with them, their relationship with each other…
“So yeah, my advice? Get a dog.”
There’s a moment in Love Hard when Nina Dobrev’s Natalie tells Yang’s Josh that the reason he’s having trouble dating is because he’s hiding his strengths. “And what strengths are those?” Yang as Josh asks. The scene is written as a turning point in their relationship, but that line—when seen in the context of Yang’s career and all the stereotypes traditionally associated with Asian men—somehow collapses the moment, reckoning with Yang’s own potential as a leading man and the odds stacked against him.
In this next chapter of his career, it’s a question directors, producers, and casting agents will be asking themselves, as he swings big and goes for roles and projects that they may not think Yang is a natural fit for.
“I would love to work with—I mean, the no-brainers, man,” Yang tells me. “Chris Nolan. Tarantino, the Daniels, Spielberg—all of those guys. Or Ruben Östlund, or many, many talented, newer directors also. And Damien Chazelle, P.T. Anderson, Wes Anderson… I would love to be in that conversation instead of just, ‘Hey, he’s the funny Asian guy,’ or, ‘He’s the Asian actor.’”
For so long, Hollywood responded to calls for diversity with what Hilton Als called the myth of The Only One—space for only one Black comedian, one Asian actress, one queer actor. That put an undue amount of pressure and attention on the efforts of the ones who did make it. “There is no way to win,” Lucy Liu said in a recent interview for The Cut.
Yang’s generation enjoys the privilege of reaping the benefits of the battles Liu and her contemporaries fought for the community. And for Yang’s generation, the myth of The Only One is dead. “There’s not just one white leading man. There’s Matthew McConaughey, there’s Tom Hanks, there’s Matt Damon, whoever—and why not for the Asian community?
“If I really get competitive, I should get competitive with Ryan Gosling. I should get competitive with Austin Butler, Tom Hanks, or Michael B. Jordan as well as Steve Yeun. And you are talking to the most competitive person! I still have that in me. But it’s like, man, let’s look at the bigger picture. We don’t have to just be competitive with each other.”
After the success of Crazy Rich Asians came a flood of Asian-American and Asian-fronted projects in Hollywood. In 2021, for example, Henry Golding starred in Snake Eyes, the third instalment in the successful G.I. Joe series, and Gemma Chan led the all-star ensemble of Marvel’s Eternals. Both projects underperformed primarily because they were released in a world still grappling with Covid, but bottom lines don’t always have asterisks.
The Filipino-American comedian Jo Koy, a friend of Yang’s whose Easter Sunday was trumpeted as a historic Hollywood project for the Filipino-American community upon release last year, knows this firsthand. “The door’s open, but there’s still this whole proving situation that we have to get through,” Koy says. “We just gotta continue to keep it open. And it’s hard, man. I’m not going to lie. It closes real fast and we just gotta keep knocking that shit open, bro.”
It’s why Yang is determined to foster a community of support. “If Beef is awesome, Interior Chinatown could be awesome also,” Yang tells me. “If Crazy Rich Asians does well, then they’ll green light a couple more movies that will give us the opportunity to shine also.” And it’s community that’s given him a road map for the future.
In 2019, Yang set up a production company with fellow Asian-American creatives in Hollywood. The group originally started as a social club for like-minded friends to get together to eat crab, so they decided to call the company Crab Club. The goal, Yang says, is to become “an A24.” (In 2021, Crab Club signed on to write The Great Chinese Art Heist for Warner Bros., based on a 2018 GQ article, with Jon M. Chu attached to direct.)
“It’s great to do important projects, but these important projects have to be entertaining. One of my favorite films this past year was Triangle of Sadness,” Yang says, referring to Ruben Östlund’s Palme d’Or winner. “I think that’s why Crazy Rich Asians did so well. It was a watershed moment but it was so freaking entertaining. I’m not watching it like I’m watching some of these Oscar screeners, like a film studies class.”
A day after I visited the Yang-Kimmel residence, I met with them for their shoot at a restaurant in Los Angeles that had once been in Chinatown—the Roman Polanski classic, not the series. With its blood-red leather banquettes and stained-glass windows, it’s a natural signifier of Old Hollywood opulence. Today, though, it’s owned by Koreans, and serves Korean-style fried chicken. As Kimmel is getting prepped, Yang asks the styling crew to take in her beauty. “Look at that!” he says. “Doesn’t she look so good? Doesn’t she look beautiful?”
“Oh my god, you sound like a dad!” Kimmel responds, laughing. “That’s a very dad thing.”
Among the team assembled for the shoot is William Pepper, Yang’s 23-year-old Chinese-Vietnamese assistant and social media manager. Pepper got the job by cold DM-ing Yang in 2020, telling him Yang should activate his TikTok because clips from Good Deal were going viral.
Surprisingly, Yang responded and gave him a shot. “He grew my TikTok from nothing to almost four million followers,” Yang says. Pepper was on a pre-med track, but he secretly always wanted to be a comedian. A year later, Pepper moved from Arizona to Los Angeles to work for Jimmy full time.
Pepper says that when he first told his parents about his dreams, his dad told him, “Son, I know you have this dream but it’s not going to happen.” For people like them, he reasoned, it’s impossible to make it in Hollywood. But working with Yang has transformed Pepper’s life: Whenever Yang is on tour, he’ll sometimes let Pepper open for him. Just throws him out onstage with little to no warning. “First time he did it, it was 30 minutes before the show,” says Pepper, “and Jimmy just said, ‘Go ahead and do five.’”
“When [my parents] saw me on tour with Jimmy, they were like ‘Okay you can make enough to pay rent,’” Pepper says. Recently, Pepper himself booked an Amazon commercial as a talent. “Now my parents are all in.”
As Pepper and I chat, Yang reenters the room in shades and a sheer Saint Laurent by Anthony Vaccarello top, looking like the second coming of ‘90s Leslie Cheung. He’s never worn clothes this daring before, and Yang seems to relish playing the role of the peacocking rock star.
But it’s just an act. Later, crouched in a red leather booth, he tells me about a dream he has for himself. “I tell my girlfriend, I have this funny fantasy,” Yang says. “When I get old, I just want to sit in disguise at a comedy club bar. Nobody knows who I am but I’m paying attention. If a new talent [kills it], someone who has the grit and fortitude, someone who really wants it, I want to make some calls and help that guy out.”
“That,” he says, “is what I really want to do.”
PRODUCTION CREDITS:
Photographs by Christian Soria
Styled by Rachael Wang
Grooming (for Jimmy) by Hee Soo Kwon using La Mer
Hair (for Jimmy) by Will Carrillo using Balmain Hair Couture
Hair and makeup (for Brianne) by Diana Larionov using Hourglass Cosmetics
Tailoring by Yelena Travkina
Special thanks to The Prince, Los Angeles