The joke is met with subdued confusion, furrowed brows commingled with strained laughter. One guy manages an “oooof” out of appreciation for the sheer savagery of the jest, but it is clear that most people in the room do not understand its context: for Asians, even harmless queries about their ethnicity can be irrita­ting. As someone who has heard variations of the “Where are you really from” question a few too many times, I am delighted to see an Asian woman address the frustration of realising, over and over, that your ancestry generates more interest than your personality.

But Asian-American comedians who attempt racial jokes often have a harder time than those of other races, even in a city as diverse as New York. Stand-up comics divide performance spaces in various New York neighbourhoods into separate “rooms”. Harlem has the “black room”. Washington Heights has the “Hispanic room”. In the East Village, there’s the “tourist room”. Bushwick and Williamsburg co-own the “hipster room”; Park Slope’s “NPR room” beckons a similar but slightly older cohort, with steadier jobs and New Yorker subscriptions.

Yet the city that’s home to more than one million Asians has no “Asian room”.

In the past decade, the comedy scene in Asia has grown rapidly but it is still embryonic. Bold new comics struggling to navigate government censors and the taboo topics of sex and politics may envy their peers in America, where no joke is so offensive as to warrant punishment. Asian-American comics, though, face their own challenges in finding success: discrimination, parental resistance and the struggle to establish definitive cultural identities.

For years, Asian jokes have been mired in lazy and derogatory stereotypes. The “chink” gags; the small d**k gags; white dudes making punchlines out of Asian girlfriends, a phenomenon the comic Jenny Yang referenced in an Elle magazine column: “But what’s even weirder is when I put my fingers inside of her, I pulled out a fortune.”

Only recently have things begun to change. The cross-cultural success of stand-ups such as Ali Wong and Hasan Minhaj has revived the radical notion that Asians can, in fact, be funny. Last summer, the romantic comedy Crazy Rich Asians, Hollywood’s first studio film with an all-Asian cast in a quarter of a century, redrew the cultural landscape. With tens of thousands of sold-out showings and US$240 million in global ticket sales, the movie has led critics and consumers alike to reconsider the marketability of Asian lead actors and stories on screen.

“What I loved about Crazy Rich Asians is that it’s not a good movie,” says Bryan Yang, a Hmong stand-up who has written for late-night shows. “A lot of Asians thought that we had to make a good movie or we won’t get another chance.” The mediocrity of Crazy Rich Asians proved that Asian features, just like white and black ones, need not be excellent to succeed at the box office. Tellingly, the film also traffics in stereotypes: the overbearing tiger mother, the ingrained obsession with name and status, the ultra-rich’s affinity for knock-off designer handbags. But the fact that it’s made for an Asian audience constitutes a triumph in subversive comedy.

Increased representation on the screen has also elevated Asian humour from a mishmash of hackneyed tropes to more sophisticated twists on bizarre – and endearing – cultural quirks. At the Golden Globes, the Korean-American actress Sandra Oh prescribed pepcid to the cast of Crazy Rich Asians, a reference to the fact that Asians lack the genes to properly digest alcohol. When co-host Andy Samberg expressed confusion, Oh responded, quite delightfully, “Don’t worry about it; joke’s not for you.”

Meanwhile, several Asian critics penned think pieces addressing the regressive nature of comedian Ken Jeong’s Netflix special, which features no fewer than five references to his “tiny ding-dong” and some uninspired spins on the homonyms “Ho”, his wife’s surname, and “hoe”, the slang for whore.

In this climate, a group of young Asian-American stand-ups in New York are attempting to break through with provocative humour that speaks to the rich and often painful Asian immigrant experience. But unlike in Asia, the patrons at small club shows – the only realistic starting point for novices – are primarily white and male. For an Asian comic, personal stories have to be both funny and digestible to non-Asians.

“You can’t apply the scientific method in comedy,” says Fumi Abe, a seasoned stand-up who has opened for Ronny Chieng, of Crazy Rich Asians and The Daily Show. “But you have to strategise and ask yourself, ‘Does this punchline make sense to different people?’”

Building rapport is crucial when you can’t count on the audience to grasp obscure references without guidance, Abe continues. To grab the attention of the audience at the Comic Strip, an Upper East Side club popular with middle-aged Jewish couples, he opened with a relatable relationship joke. Once he had their attention, he began riffing on racial slights, such as the derogatory views some white women hold about Asian men.

For some Asian comics, the instinct at first is to draw as little attention as possible to their race.

“I think I made zero Asian jokes my first year,” says Alvin Kuai, who began performing stand-up at the same time as Watson. He says he didn’t want to be pigeonholed as a “minority comic” before he could develop his own voice. However, “getting better at comedy is ultimately trying to reach a deeper level of honesty,” he says. “If you’re trying to be honest onstage, race is a subject you can’t avoid.”

Kuai, 25, has short black hair and hooded eyes that convey a surprising amount of warmth when he smiles, which is often. Raised in the suburbs of Virginia, he had a typical Chinese-American upbringing that featured violin and piano, wushu (Chinese martial arts) and enviable grades in high school and college. But he’s also as charis­matic as most Asian kids who grew up with lots of white friends are; he probably spent less time than the average Asian youngster on trying to fit in.

When Kuai decided to start performing stand-up comedy three years ago, he was making close to six figures a year as a management consultant at McKinsey & Company, in Atlanta. For a while, he tried to work full-time and do stand-up at night, but he could barely manage to attend one open mic – informal live shows at small venues – every two weeks. Due to constant rustiness, he says, “I would bomb all the time.” So in February 2017, he quit his job and moved to New York, to pursue comedy.

His daily schedule now is no less hectic than was his 80-hour-a-week corporate job. From 8.30am to 4.30pm, he works as an office clerk in Midtown Manhattan – a day job to pay the bills. From 4.30pm to past midnight, he performs at least two sets around the city. (Altogether he partakes in about 30 open mics and booked shows a week.) At the end of a long day, he retreats to a Hell’s Kitchen walk-up that he shares with five other people. The six cramped bedrooms separated by paper-thin walls probably represent a fire hazard, he says.

“My parents hate me,” Kuai says, casually. “My dad actually tried to physically fight me.” Since arriving in the city two years ago, he hasn’t visited or talked to his parents.

Kuai’s older sister, Rena, saw the stalemate in her family as a microcosm of the generational clash within the Asian diaspora. Immigrant parents and their American-born children are chasing different versions of the “American dream”, pitting stability against passion as the key to a fulfilling life. She recalls her mother crying after seeing Kuai’s apartment for the first time. Although her father’s reaction was more aggressive, she says it was out of worry as much as disappointment.

“Our parents came to this country and had to work really hard to make sure we have a good life,” Rena says. “They just wanted him to stay on a stable path.” Her brother saw that as an invitation to give up on his dream. “[Kuai] told me, ‘If you have a backup, that just means you think you won’t be successful.’”

Kuai recently reconnected with his father by email, though they’re not yet on speaking terms. At times, he seems torn between telling his father about the hardships he has endured and wishing the older man would reach that understanding on his own. Kuai seems also to have accepted that he has chosen a thankless career riven with strife and isolation.

“Comedy is its own world and it pulls you in,” he says. “But I still have confidence that my relationship with my parents will be fine.”

Until the 1970s, virtually all the well-known stand-ups in America were white. Then a group of now-legendary figures – Redd Foxx, Richard Pryor, Eddie Murphy – crossed into the mainstream and put black comedy on the map. They delivered searingly funny yet honest material that captured the painful reality of being black in America and paved the way for modern stars such as Chris Rock and Dave Chappelle.

At that time, a number of Asian comedy groups emerged in the San Francisco Bay Area. Plenty of talent was spawned but no Pryor or Chappelle-like visionary who spoke defini­tive­ly about the Asian-American experience, sold out theatres and inspired a generation of Asian kids to become professional joke tellers.

In the 1980s, Henry Cho, a Tennesseean with Korean roots and a thick Southern accent, did find success upend­ing stereotypes in front of white audiences. Over a 30-year career, Cho, now 56, has performed on the Tonight Show and become a movie star. But even at the height of his popularity, he wasn’t able to engage with the Asian-American community.

“There was always a cultural and language barrier that kept that from happening,” Cho says. In 1990, more than half of the Asian-American population spoke only limited English, according to the Census. It was tough winning over a group of people who didn’t understand what he was saying, Cho says, so it made no sense, then, for a comedian to share with their audience what it was like to be Asian.

“Black comedians get to talk about it because their audiences are predominantly black,” says Cho. “Where is that support for us? We never saw that, and still don’t see it.”

It was Chappelle’s subversive humour that left the big­gest imprint on the Asian comics who came of age in the 2000s, including Watson, Kuai and a handful others inter­viewed for this article. As the Asian presence in comedy grows, Kuai hopes that his generation will follow the trajectory of black comics and more pointedly address misconceptions about their culture. The Asian diaspora has also changed markedly since Cho’s youth. Over the past 20 years, their population has risen by 72 per cent, according to data from the Pew Research Center. Some 70 per cent of Asian-Americans now speak English proficiently, though the figure fluctuates across ethnicities.

“I think there’s an opportunity to really go into depth about the racism that we face,” Kuai says. “The perception of us is rooted in stereotypes. A lot of people perceive us as being entitled, as having the same status as being white.”

But satire has hardly proved to be a silver bullet when it comes to combating racism. Black comics still face some of the same challenges as their Asian counterparts. Charles McBee, 36, writes for MTV and has performed at all the major clubs in New York. He says he won’t adapt his jokes but admits that entertaining white audiences can be laborious. Before telling a blackface joke, for example, he makes sure to touch on the history of the practice, to explain why it’s so problematic. But in black rooms, he says, “I can just go, ‘It’s crazy, right?’ And people will get it.”

Watson hasn’t always felt comfortable address­ing Asian stereotypes, partly because she is racially ambiguous. In fact, her almond-shaped face is such a harmonious blend of Western and Eastern features that she looks a touch Native American. Yet she introduces herself as a Japanese-American woman from Lakewood, Ohio; a “very white neighbourhood of Cleveland”. During the second world war, her maternal grandparents were sent to an American internment camp, prompting her mother to devote her life to the freeing of political prisoners.

In 1998, when Watson was 10, her Scottish father was arrested for burning an effigy of Chief Wahoo, the mascot of the Cleveland Indians baseball team, which many consider is racist towards Native Americans. In class, a teacher said the protesters were arrested but not held. Watson was a shy child and hated the spotlight, but she felt compelled to speak up: the protesters had actually been detained, for at least 24 hours, and she knew that because her father was one of them.

“Everyone started laughing at me, and I just turned very red,” Watson recalls. “Then I started laughing, too.” She didn’t know it at the time, but that was the moment that would push her towards comedy years later. “That was when I gave up ever trying to fit in or win a popularity contest,” she says, “because that just wasn’t on the cards, the way that my family was.”

The trauma and discrimination her family endured taught Watson about “all the bulls**t in the world”, she says. Yet she still felt she was “too white” to joke about certain aspects of Asian culture.

In 2018, a year after she began performing comedy, Watson became so fed up of having her identity questioned by both Asians and whites that she decided to forgo her Anglo-Saxon birth name (which she’d rather I not state) and adopt Yoshiko, her middle name. She says that doing so allowed her to take control of her own identity, and she likes that her full name describes who she is: half-Asian, half-Caucasian.

Even so, performing at shows with all-Asian line-ups, which these days often draw healthy Asian crowds, can be both empowering and unnerving.

“They’re so fun,” she says. She doesn’t have a trove of Asian jokes, but she feels emboldened to write ones for these occasions. And when people cheer, she wonders, “Is this what white comics feel like all the time?” Yet, “I still get nervous because I worry they’ll think that I’m clearly not full-Asian.”

As part of the otherwise muted celebrations for May’s Asian Pacific American Heritage Month, more than 100 young Asians filled the Upright Citizens Brigade Theatre, in Hell’s Kitchen, on May 10, to watch Asian AF, a variety show featuring performers and comics of Asian descent. The acts unfolded like a greatest hits album of diasporic jokes that only Asians would get.

AzN PoP!, an all-female parody band, sang catchy tunes about, among many other cultural offences, the emetic coupling of cream cheese and sushi. A collective jeer erupted when a projector streamed a video of actress Emma Stone gushing about how honoured she felt to play an Asian woman in the movie Aloha.

As the night progressed, it became clear that Asian comedy couldn’t be entirely divorced from politics, and maybe that’s not a bad thing. When headliner Ronny Chieng stepped onto the stage in a baseball cap and mustard tee, the crowd seemed to anticipate not only laughs but a catharsis of sorts. His climactic joke sounded less like a swipe at draconian parental expectations than a teaser of what could be possible for America’s fastest-growing racial group.

“Think of how inspirational it would be if we have the first Asian president,” he said, arms extended and hands balled into fists. “We could finally go up to Asian children anywhere in America and say, ‘Hey listen, buddy, you don’t have to be just a neurosurgeon any more.”