The Complicated Philosophy of Jay Smooth

A cultural critic and multimedia savant breaks up with his radio show after 30 years

Illustration: McDavid Henderson

In July, on Friday the 13th, Jay Smooth, a 45-year-old cultural critic, video blogger, and DJ was preparing to host another edition of Underground Railroad, his two-hour hip-hop and culture show on WBAI, the New York affiliate of Pacifica Radio. That evening, he wore a light red button-down shirt and glasses with currant-colored frames; his hair had been buzzed so short that his head was almost bare. The son of a white Jewish mother and a black father, Smooth describes himself as having an “ethnically ambiguous” appearance—strangers have mistaken him for Arab, Latino, and white. He hurried into the WBAI office, on the third floor of Brooklyn Commons, a “radical movement-building space” in Boerum Hill, arriving at the station’s single studio, where four black-and-gray IKEA bath mats help muffle sound and a cluster of red Christmas lights indicate when an anchor is on-air.

You may not have heard of Jay Smooth, but his career has influenced the way a lot of journalists—as well as people outside of media—think and talk about music, culture, and modern life. He started his show in 1991, when he was 18 years old, which makes Underground Railroad the city’s longest-running music program. (“I am the composer, arranger, and conductor of the Underground Railroad,” he’s told listeners.) Since then, fans have tuned into 99.5 FM to hear hip-hop interspersed with Smooth’s riffs on the news of the week; in recent years, listeners could reach him during the show via an online chatroom while he had intimate conversations with DJs and artists such as TLC, A Tribe Called Quest, and The Fugees—many of whom he first interviewed when they were in the early stages of their careers.

Smooth’s ability to listen, analyze, and react—both in conversations about hip-hop and in national discussions about race—has propelled him into a rare kind of internet virality. In the summer of 2008, a few months before the election of Barack Obama to the presidency, Smooth uploaded a video to YouTube called “How to Tell Somebody They Sound Racist.” In a close shot filmed in black-and-white, Smooth, wearing a T-shirt, addresses his audience against a hip-hop backing track. “Everybody’s talking about race right now,” he says. “And when everybody’s talking about race, that means sooner or later you’re going to need to tell somebody that they said something that sounded racist.” In just under three minutes, he smartly sums up how to understand the difference between “what someone did” and “what they are.” He explains, “If that dude really is racist, you want to make sure you hold him accountable and don’t let him off easy.” Over a decade, the video has racked up more than 1.26 million views and is now required viewing material in some college classes.

Smooth’s ability to listen, analyze, and react—both in conversations about hip-hop and in national discussions about race—has propelled him into a rare kind of internet virality. 

As the audience for his work grew—he also maintains a blog, Hip Hop Music, and a video site, Ill Doctrine—so did demand and attention from prominent media outlets. He was hired to produce videos for XXL, a music site; Fusion (now Splinter News); and Race Forward, a nonprofit racial justice organization. Smooth was featured on NPR’s All Things Considered, spoke as a panelist on All In with Chris Hayes, interviewed Drake for a revealing feature in The Village Voice, and appeared on Totally Biased with W. Kamau Bell. In November 2011, he gave a TED Talk at Hampshire College called “How I Learned to Stop Worrying and Love Discussing Race.” In it, Smooth told the audience how frustrating conversations about the subject can be. “Race is a social construct that wasn’t designed to make sense,” he said. The rules of conduct “were shaped to defend indefensible acts,” he went on. “Being a good person isn’t a fixed characteristic—it’s a practice.” In 2016, Smooth began booking paid speaking engagements, often on topics related to race and politics.

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Through all his other endeavors, Underground Railroad remained Smooth’s home base, a “secular church,” he says, where he and his friends could gather every week. It also remained a labor of love, since Smooth and his colleagues were never paid for their work at WBAI. The station prides itself on serving communities typically overlooked by commercial radio stations, which means that, although the programming is high-minded, it has a tiny audience compared to those of other broadcasters. This has left it struggling financially. Today, the station receives monthly donations from listeners, but its level of funding is relatively low.

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On July 9, The New York Times reported that Leonard Lopate—who had been terminated in December 2017 from his show on WNYC following allegations of sexual harassment—had been hired at WBAI, for a paid position, to host a new daily talk show. The idea, managers said, was to attract wide financial support.

It wasn’t until a few days later that Smooth heard the news, just hours before he was scheduled to go on the air—his timeslot was 10pm to midnight. Lopate’s hiring made Smooth nervous about the direction in which WBAI would be headed. “I think it’s a terrible idea,” he told me that evening, his face scrunched with concern. Smooth seemed introverted and nervous—a stark difference from his personality on the radio and in videos, where his voice booms with confidence. He said that he wanted to figure out if the decision to hire Lopate should prompt him to speak out—to management, to his listeners, to other people at the station—and he wanted to make sure he had all the facts. With only a few minutes before his show was supposed to start, Smooth sought answers.

Wandering outside of the studio, he found Berthold Reimers, WBAI’s general manager. The choice to hire Lopate boiled down to money, Reimers confirmed. “How about we take sponsorships and don’t hire Leonard Lopate?” Smooth asked him. “Well, bring me the sponsorship and let’s do that,” Reimers replied. (Reimers declined to comment on this exchange.)

Soon after, in a stairwell, Smooth bumped into a gathering of producers, many of whom, like him, had been hosting shows for two or three decades. Mimi Rosenberg of Building Bridges, a show about labor and community affairs, told him about a list of names she’d been gathering for a letter protesting the hiring. It was now just past 10pm; Smooth’s start time had come and gone. He signed Rosenberg’s list and walked down the hall before realizing that his booth was empty and he was broadcasting dead air.

Before he adopted the name “Jay Smooth,” John Randolph was a shy kid from the Upper West Side of Manhattan. Born in 1972, his mother—a jazz pianist who made her living as a legal secretary—and his father—a poet who worked as a receptionist at Friends Seminary, a private Quaker day school—split when he was four. Randolph’s life was divided between his mother’s neighborhood, which was rapidly gentrifying, and Harlem, where his father had a low-rent apartment.

For most of his childhood, in public school, Randolph participated in a gifted and talented program. In eighth grade, he won admission and a full scholarship to Fieldston, a private school that caters mostly to the children of New York’s elite. His experience there was excellent academically, but he also understood that it was a place of great privilege. “It’s a rich, white, liberal school where people can definitely be deluded about how pure and virtuous that makes you,” he says. Randolph attended at the same time as Soon-Yi Previn, Sean Lennon, and Maggie Haberman, but his friends were mostly other boys who were also minorities, scholarship recipients, and graduates of the same gifted program. Randolph wasn’t bullied “in the traditional sense,” he says, but he felt invisible on the margins. “I was known as the kid who always looked at the floor and never talked,” he recalls. “I believed that I was a freak that would never connect with other kids.”

For Randolph—deeply thoughtful, often reserved—hip-hop offered an escape in words. He memorized lyrics and found their hidden messages. He fell in love with records like 8th Wonder by The Sugarhill Gang, The Message by Grandmaster Flash and the Furious Five, as well as artists like Run DMC, Rakim, and Big Daddy Kane. “The beat that they’re rapping over is a scavenger hunt,” Smooth said in 2013 during a talk at the XOXO Festival. “An endless world for me to lose myself into when I was growing up.” By the late 1980s, hip-hop was becoming popular in the mainstream white world, too. “There was a sudden point when every kid at Fieldston was blasting Kool G Rap out of their Saabs,” he recalls.

The music of the South Bronx was also the perfect haven from what was a difficult childhood—Randolph’s father had mental illness and suffered from alcoholism. “What I had modelled for me growing up is, whatever positive regard you get for yourself in the world, that’s a facade that you’re successfully keeping up,” Smooth says.

In 1989, at 16, Randolph needed a job. A McDonald’s rejected his application. His mother, a longtime listener to WBAI, heard Anthony J. Sloan, a producer and arts director, announce on the radio that the station was hiring production interns. In addition to producing the evening news, Sloan was also behind Randolph’s favorite programs: Creative Unity Collective, a black political sketch comedy show, and bi-annual specials dedicated to Prince. Randolph prepared a voice audition. “Reading something off a piece of paper happened to be something I was really good at,” he says.

He was hired. Sloan, responsible for teaching Randolph how to do his own engineering and cut his own tape, says that his student transformed like Robin Williams’s character in the 1987 movie Good Morning Vietnam. “It was just like that,” he recalls. “On the air, Randolph sounded like a 35-year-old. He didn’t sound like a kid.” Sloan, who would attend Randolph’s graduation from Fieldston, quickly saw how thoughtful this “older spirit” was, as well as his dedication to hip-hop. “He was calm, collected, and carried himself in a mature fashion. There was no messing around.”

“This regime of constant trolling, bullying, and gaslighting challenges me to figure out what I can best contribute.”

After several months, Randolph—by then 17—wrote a proposal for a hip-hop show so impressive that management initially thought that it was ghostwritten by Sloan. The timing was also good; WBAI had been looking for ways to expand its audience. “I wanted to do something that correctly represented the music and culture,” Randolph says. Commercial hip-hop radio stations like Hot 97 didn’t exist yet; to hear the latest music, fans had to go to stores and buy records, or hear tracks at dance parties. “I wanted to live up to the same standard of all the underground shows that I grew up on,” he says. The leaders of WBAI gave him the go-ahead.

Underground Railroad debuted on February 3, 1991, during Randolph’s senior year of high school. (“If I was choosing a name now, I’d probably say that it’s kind of presumptuous for me to imbue this project with everything Harriet Tubman did,” he says.) His stage name came from something his father said in response to hearing one of his pause-button mixtapes: “The boy’s smooth.” Sloan executive produced the program in its first year. “There was no nervousness,” he recalls. “I think he had it from the beginning.” (Starting in the early 1990s, Glenn “G-Man” Holt joined Smooth as an occasional co-host of Underground Railroad, until he died, last summer.)

Since then, Smooth has had to find ways to earn a living. He was a counsellor and assistant teacher at a group home for kids up in Westchester; he took some dot-com jobs—first in customer service, then in programming—and he played online poker. In 2007, he landed an interview facilitator position at StoryCorps, a nonprofit that records pieces from the lives of people “of all backgrounds and beliefs.” The job helped Smooth realize that he wanted to do creative work that could develop the skills he had learned from radio into a new kind of storytelling—first person, straight-to-camera essays.

Around this time, Smooth shared an apartment with Jason Reynolds, a StoryCorps colleague. Reynolds remembers his roommate shooting and editing in his room for hours. When Smooth was done, Reynolds was astonished—there was a dramatic personality difference between the timid person he knew and the assertive character he saw on-screen. “It was like Clark Kent and Superman,” he says. “It was amazing.” These videos would become Smooth’s first posts to Ill Doctrine.

It didn’t take long for video to become Smooth’s medium of choice, a new place to confront offensive rhetoric and racist speech. “One of my favorite things about hip-hop is its everlasting love of language,” he says in the introduction to a video on the problematic use of the phrase “no homo.” He continues, “One of my least favorite things about hip-hop is our everlasting fear of being gay.” In another video, about respectability politics, Smooth lays out the problem with advocating that systemic injustice against black Americans can be solved through changes to their own behavior (often suggested as insulting counsel, like “pull up your pants”): “Advice that’s valid in the abstract but totally useless in context.” He’s also done media criticism about Bill O’Reilly’s anger over Nas and spoken out about domestic violence in the hip-hop community.

For Smooth, video blogging was also a way to become more comfortable with himself. Before he started Ill Doctrine, he didn’t have any mirrors in his apartment except one, in his bathroom. “I didn’t have it inculcated in me to care about or like my physical appearance,” he says. But he is conscientious about how his work is received—creating videos, in particular, can be a high-stress undertaking—so adjusting his facial expressions and body language on camera became a natural part of the production process as he strove for perfection. His video-making was successful enough to earn him money, although, given his inclination toward independence, he has not always enjoyed working in partnership with media companies. “It dilutes and distorts the process, even if they’re not making specific demands,” he says.

Smooth has also struggled with the dynamics of television news panels. “With very few exceptions, no one can really go on one of those shows and genuinely listen to a question—listen to it—and give a genuine answer,” he says. “It’s very difficult to have a real, intellectual, curious conversation.” In 2015, during an appearance on All In with Chris Hayes to discuss a Starbucks campaign called #RaceTogether, Nancy Giles, a CBS journalist, teased Smooth about the “brother-like” way he talks. “I’m a rap guy,” he replied, and then flashed her a tight smile. She accused him of co-opting certain “black” mannerisms. In response, Smooth blurted out, “I’m actually black, but you assumed otherwise, and this is the sort of awkwardness we can look forward to in Starbucks.”

After the show aired, Smooth became a trending topic on social media. The attention upset him, and he channeled those feelings into a video: “It was the longest 30 seconds of my life.”

On that July night at WBAI, after rushing into the booth, Smooth started the episode of Underground Railroad, belatedly, with “Stand!” a 1969 song by the rock-soul-funk band Sly and the Family Stone. (“In the end you’ll still be you / One that’s done all the things you set out to do.”) After playing a few songs and talking about politics in Europe, he made note of Lopate’s new show. “On the topic of taking a stand,” he said, “I do not want any sort of silence on my behalf to indicate any sort of support or acquiescence to this decision.” He took a deep breath, then told listeners that he was “vehemently opposed” to WBAI’s decision. He expressed hope that Lopate’s hiring would be reconsidered.

It wasn’t. On July 16, Leonard Lopate at Large premiered. A few days later, Smooth informed WBAI management that he was leaving, less than a year before his 30th anniversary at the station. He announced his decision on Twitter with a screenshot of his Facebook profile, showing his change of employment status at WBAI: July 1989–July 2018.

On a rainy evening two weeks after his last show, Smooth and I met up at a coffee shop in the Dumbo neighborhood of Brooklyn. In ending Underground Railroad, Smooth said, he felt obligated to live up to his values. Confronting WBAI’s management “set in motion a process that led to me choosing to leave the station right then and there,” he explained. “When you’ve put your heart and soul into trying to make something work and built all these deep friendship and connections in this place, it takes a lot to reach the point where you just say, ‘I think I just gotta cut this off and walk away.’”

Smooth found solace in friends and supporters, who include notable journalists like Ta-Nehisi Coates, hip-hop luminaries like Just Blaze, DJ Jazzy Jeff, and Chuck D, and comedians like Aamer Rahman. His father’s health has improved, and they are now on good terms. But in the days after he pulled Underground Railroad, he felt unmoored. Jiun Kwon, his partner of many years, had died in 2015; at her memorial, he’d said, “I feel like I don’t know what to do now because she was the person I wanted to talk to about everything every day.”

With Underground Railroad no longer in his life, the gap had him wanting another creative outlet to engage him in conversations on hip-hop and social justice. Early this year, he hosted a media literacy series for Crash Course, a popular educational YouTube channel with more than 8.2 million subscribers. Recently, he has been creating audio Easter eggs called “Secret Transmissions”—podcast episodes he produces and uploads to sites like Mixcloud and HearThis.At.

Smooth remains popular online—he has tens of thousands of followers on Twitter, Facebook, and YouTube, where he posts videos like his conversation with Tarana Burke, the creator of #MeToo. He earns money through a Patreon, a crowdfunding platform designed to provide creative people with recurring financial support, and through his speaking gigs. Yet keeping up with news, especially the Trump administration, is not easy for him. “This regime of constant trolling, bullying, and gaslighting challenges me to figure out what I can best contribute and what is the work that I can maintain in a healthy way for myself,” he said. He’s careful not to call himself an activist, though he aims to provide “a support system for people who are out there doing the work and trying to push forward,” he explained. “I hope to make videos and do other work that you can use as a reference.”

Smooth told me about his father, whose demons and circumstances had kept him from making the most of his creative talents. With that in mind, Smooth is proud of where he’s landed today—rather than bylines in certain publications or benchmark YouTube subscription numbers, he largely measures the success of his work by being able to do what his dad didn’t.

I asked Smooth if he had plans to quit media and try something new. He laughed. “That’s always a looming possibility in my mind,” he replied. But taking on any kind of full-time employment is something he would do only if it were the right fit. “It’s not just about having some noble ideas, it’s about my fragile psyche,” he explained. “It’s enough of a struggle for me to believe I should be putting myself out there. I’m not selling my life path as something that is or should be replicable, but it’s just, it was the path for me.”

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Karen K. Ho is freelance business, media and culture reporter, as well as a former Delacorte fellow, based in Toronto and New York. She is a former Delacorte Fellow at CJR. Follow her on Twitter @karenkho.