UNTIL VERY RECENTLY, the character of Long Duk Dong in John Hughes’s 1984 movie “Sixteen Candles” was a kind of stock figure who stood in for our culture’s perception of the Asian man in America. He was an exchange student of ambiguous origin living with the white Baker family. We first meet Dong, who is played by the Japanese-American actor Gedde Watanabe, after he hangs his head over a bunk bed in front of Samantha, played by Molly Ringwald. “What’s happen’n, hot stuff?” he asks her, in a thick, placeless accent. A gong sounds. Ringwald’s face registers disgust. Later, in another scene, Dong is facedown in the grass, still intoxicated from a party the night before. He looks up at his American host family: “Ohh, no more yanky my wanky! The Donger need food!”

Laughter ends, but it can be hard to shake whatever false truths are bound to a joke. When the comedian and actor Ken Jeong jumped out of a car naked in the 2009 comedy film “The Hangover,” his flaccid penis got a laugh. Jeong later defended the scene, saying in an interview that it was his suggestion, his decision and his penis. But weren’t they — weren’t we — laughing at his expense? Did it not reinforce what we as a culture are taught to think of Asian men generally?

The heart of comedy is the element of surprise, the way a joke can weave around a room, tell the sympathetic story of someone’s life and then suddenly turn and slap you in the face. The deftness of a comedian lies in his ability to judge the severity of the joke’s transgression — of knowing when and where to cross the line. A good joke can end a quarrel; a bad joke can get someone kicked out of the party. A great joke, however, is inseparable from its ability to subvert, to say the unspoken or unspeakable. When we laugh at the joke, we laugh despite the discomfort. We laugh knowing we’ve just witnessed a taboo dash across the room like a streaker on a soccer field. Comedy gives us permission to let an unspoken thought free.

When I speak to Booster about his humor, I perceive that he feels a sense of responsibility — if not to carry the oppressive, overwhelming burden of representation, then to question the foundation upon which certain stereotypes are built, stereotypes that he has employed in his own routines. He tells me that as his career grew, he started performing more and more to predominantly Asian audiences. His jokes began to change. He says, “I used to have jokes that talked about how it’s funny that I’m adopted and yet I’m still a bad driver. It must be genetic.” When I looked up his older clips, I could see that Booster was already pulling apart the joke — separating his personal incompetence behind the wheel of a car from the stereotype of bad Asian drivers. Here he is in 2017: “But actually, you guys, that might have more to do with being gay and sleeping with men than it has to do with being Asian. Something about being lied to my entire life about what six inches look like — now my depth perception is [expletive].” The audience laughs uproariously.

A great joke is inseparable from its ability to subvert, to say the unspoken or unspeakable.

“I am a bad driver,” Booster tells me. “That’s not me making that up.” But it didn’t sit well with him to perpetuate a tired stereotype. “Every time I get honked at by a person, it comes from a real place of turmoil. My brain is like, ‘I’m confirming a stereotype right now for a person.’ And that is a weight white people don’t have to carry around.”

The actor and comedian Jimmy O. Yang, who plays the mercenary Chinese app developer Jian-Yang in the HBO series “Silicon Valley,” says that comedy was where he found a sense of belonging as an immigrant from Hong Kong. Humor allowed him to access a deeper sense of self-awareness, and telling jokes allowed him to find people who were trying to translate their experiences as he did: “In stand-up, honing material gets more specific and more truthful. In the very beginning, it’s just about me jerking off, right? Then it became about me being Asian — very broad, dumb jokes. Stereotypes that were not specific to me.” But Yang soon began to subvert the jokes, to question assumptions about his identity and his experiences. “When I was growing up,” he tells me, “I was super stereotypical. I played the violin. I was pretty damn good at math. I played Ping-Pong competitively, all that stuff. But those things weren’t stereotypes when I was growing up, because I grew up in Hong Kong. Everybody was Asian. That’s just what everybody did.” I bring up a bit I had seen from one of Yang’s sets from 2014 that evoked clichés of Asian masculinity. In it, he jokes about how, when he goes to the beach, he gets mistaken for a girl from behind. Then he embellishes it: “And from the front, I look like a hot Asian chick!” Yang acknowledges that it was self-deprecating. He adds: “But at the same time, how does me looking like an Asian chick matter? Am I really making a comment on Asian masculinity, or am I making a comment on how society views Asian people?”