The Root’s Ahmir “Questlove” Thompson is 43 years-old (!), has been making music for three decades (!!), and has the privilege and perspective of years. He’s also willing to share it. In this case it’s in an ongoing series of six essays entitled “Questlove’s How Hip-Hop Failed Black America” for Vulture. It is one of the smartest things I’ve read on pop culture.
In particular, “Part III: What Happens When Black Loses Its Cool?” hit home because it suggests that, as it stands, Asian America will struggle to ever generate anything close to the kind of “cool” that’s come from black America. We’ll get to that in a sec, but first let’s let Questlove explain America’s black cool.
Cool doesn’t mean a lack of temperature, exactly. It doesn’t mean low affect or indifference. It means cool heat, intensity held in check by reserves of self-possession. Cool is social engagement masquerading as a kind of disengagement. As a result, in any display of cool, there is a slight hint of threat. What if the mask is lifted and the heat released? That threat can be physical or sexual or intellectual, but it’s always felt. Look: That person has power that he or she is not using. Think: What will happen if he or she uses it? React: I don’t exactly know, but I better keep watching to find out.
What’s striking is how little of Asian American culture embodies this kind of cool. Intellectually threatening? Nah. Physically or sexually threatening? Most definitely not. In part, Asian America’s got itself to blame because it’s worked hard to embrace dominant (white) culture and be anything but a threat.
Look no further than the model minority mythology which has at its core the concepts of “safe” and “non-threatening.” Questlove argues that black cool has always been in conversation with dominant (white) culture and that its cachet comes, in part, from white culture wondering what black culture will do next. Black cool came to be because it surprised and unsettled dominant (white) America.
In contrast, when Asian America embraced the confines of the model minority it said to dominant (white) America, “See, we’re just like you! We’re hard working, smart, quiet, educated, and succeed in ways that make you feel safe. We are what you say you wish other minorities would be.” In other words, in an effort to feel superior to other races and to fit into America’s dominant (white) culture, Asian America has inadvertently limited itself to a box built by dominant culture.
To see what I mean all you have to do is look at who’s generated Asian cool in the U.S. today. It’s people like PSY and genres like K-pop. It’s stuff like manga and anime. It’s movies like The Raid and directors like John Woo and Wong Kar-wai. What do these all have in common? All of them are not Asian American they’re just straight up Asian.  They are voices and genres that don’t really care what America’s dominant culture thinks. They create and succeed on their own terms and don’t live with an eye to what America’s dominant culture likes, respects, or wants. They don’t give a damn about being a model minority.
In contrast, Asian America has cared too much about dominant American culture to generate cool. Fearlessness is cool. Not caring if you fit in is cool. Defining your own success is cool. All that is the opposite of being a safe, unthreatening model minority.
That’s not to say Asian America can’t (or hasn’t ever) generated cool individuals or ideas, but its culture isn’t fertile ground for growing cool. Perhaps that’s because to generate cool as an Asian American you have to shake the shackles of two cultures: dominant American culture and Asian American culture. Take, for example, celebrity chef Eddie Huang. Whatever coolness he generates comes because he’s refused to live in the boundaries drawn up by both his parents (get a safe, “successful” career) and the surrounding American culture (be someone that makes us feel safe). As outspoken, unconventional, and hip hop as Huang says he’s always been, the man still became a lawyer and worked for a prestigious law firm before he had the courage to walk his own path. His story shows that bucking convention is doubly difficult for most Asian Americans. 
What will it take for Asian America to generate some cool? Look no further than the don of Asian American cool, Mr. Bruce Lee. Born in San Francisco, he forced American and Asian culture to deal with him on his own terms.  Like most of today’s Asian Americans, he didn’t fit in either the old or new world. In HK the local Chinese shunned him for being part white (German); Chinese Americans decried him for teaching kung fu to white people; white Hollywood dismissed him for being too Chinese. What he did, though, was embrace the rejection and choose his own path. He couldn’t ignore his complex heritage, but he did not pander to it either. He had the courage to be something that threatened all his cultures. By refusing to follow convention, he forged something new—kung fu, kick ass, martial arts cool.
And there’s the lesson. Cool isn’t the goal, it’s the byproduct. It grows out of not automatically doing what’s expected, but instead intentionally choosing one’s own path. If Asian Americans were to unapologetically embrace our American and Asian roots but refuse to be boxed in by either, we would be free to generate new, non-stereotypical identities.
It would mean not looking towards dominant (white) culture for affirmation or assimilation. America is big enough, individualistic enough, and diverse enough to forge our own identities. It will mean, also, rejecting the comfy model minority stereotype and the “acceptance” that it brings. In the end, cool will be a byproduct of being who we choose to be.
I don’t mean to say that all Asian Americans should try to be cool. We should, however, look to cultivate an environment where each person can choose what life they want to live and not be force each other to live an automatic, “safe,” and “just fit in” lives. That’s the self-possession and power that Questlove is talking about—choose your own adventure and cool may happen by accident.
1 Endnote ↑ Questlove then acknowledges there are different kinds of cool and that coolness in general has taken a hit because of things like “social networking, instant journalism, and a culture of humiliation.” Black cool has always been a conversation with the dominant (white) culture. He then asks, “But what happens when black (i.e. hip hop) culture is consumed and integrated into the dominant culture?” Just read his essay. It’s worth it.
2 Endnote ↑ This is pretty much the opposite of America’s black cool, where white America sensed the road to cool meant borrowing from domestic black culture (see, e.g. rock and roll). Unlike for Asians, white America hasn’t really looked towards the black continent (i.e. Africa) for black cool.
3 Endnote ↑ And let’s be clear. Huang’s parents were not happy when he told them he hated being a lawyer and decided to start a restaurant. Having walked away from a big law firm career myself, I can empathize.
4 Endnote ↑ Admittedly, Lee spent his first 18 years in Hong Kong, but his experience is instructive.
5 Endnote ↑ Note how American culture embraced “Asian martial arts” cool and turned it into a box/trap/stereotype for Asian Americans; sounds an awful lot like “hip hop” and “athlete” cool for black Americans, does’t it?