Top 20 Uncomfortable Moments on Ziwe

#20: Whitney Leavitt Interview

The interview with Whitney Leavitt, star of “The Secret Lives of Mormon Wives,” quickly became an exercise in trying to get a straight answer. Asked about the First Amendment, Leavitt veered into voting rights, prompting Ziwe to clarify the question. She also appeared unfamiliar with “stop and frisk,” which Ziwe also had to explain. Whenever the questions got pointed, Leavitt repeatedly suggested she would “call the press,” which sort of became a running joke. Then Ziwe asked how many Black friends she had. Leavitt’s answer, essentially, was “not enough.” The interview kept circling back to the same awkward problem: Ziwe asked simple questions, while Leavitt struggled to give simple answers. The result was painfully uncomfortable.

#19: Porsha Williams & the Underground Railroad

Anyone who watched “The Real Housewives of Atlanta” remembers the moment Porsha Williams thought the Underground Railroad was a literal underground train. It became one of reality TV's most infamous clips. So naturally, Ziwe brought it back up. To her credit, Williams had clearly done some homework; she explained the Railroad mostly accurately this time. She even promised she wouldn't say anything ignorant again, then immediately seemed to reconsider that promise in real time. Things unraveled further when the First Amendment came up and Williams drew a blank, prompting the show to deliver an impromptu civics lesson on air. Then Ziwe offered Williams the opportunity to say her final words on camera, which she used to throw shade at Ziwe.

#18: Roy Wood Jr. Questions His Nepo Baby Status

Nepotism sounds a lot less awkward when you call it a family business, and that was the argument comedian Roy Wood Jr. initially made. During his Ziwe interview, he defended passing resources and connections through generations, comparing it to a family-owned restaurant. Then Ziwe pointed out that Wood’s father, Roy Wood Sr., was a prominent civil-rights journalist who helped establish a path in American journalism. Wood pushed back, saying his father never simply handed him a career. But then he stumbled on the realization that he actually started at the same radio station where his father had worked. That seemed to stir up a minor existential crisis for the comedian.

#17: Vince Staples’ Musings

The thing about Vince Staples is that his voice is so measured and calm that you almost trust whatever he's about to say. Almost. During his Ziwe interview, Staples delivered some genuinely unhinged takes with the energy of someone reading a grocery list. Asked to weigh in on what had caused more harm to the Black community – drugs or processed sugar – Staples bypassed both options entirely and threw his own genre of music under the bus. Later, Ziwe asked which white people he would invite to the cookout. Staples sidestepped the premise and launched into a rant about homelessness. He also did well to mention how exactly he supports his friends who are unhoused.

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#16: Jaboukie Young-White's Draft Evasion Strategy

Jaboukie Young-White brought the kind of chaotic comic energy that makes a Ziwe interview dangerous. After discussing an awkward Sephora encounter, Ziwe asked him to demonstrate how he had walked into the store. His exaggerated performance prompted Ziwe to call it a “deeply offensive” portrayal. The conversation then moved to a hypothetical military draft. Asked how he would avoid serving, Jaboukie proposed leaning hard into his gayness and demonstrated what that strategy might look like. His commitment, paired with Ziwe’s straight face, made every second more absurd. It was hilarious, but also the kind of exchange that makes you wonder whether you should be laughing at all.

#15: Wanda Sykes Takes Every Single Piece of Bait

Ziwe's entire interview style is essentially an elaborate trap. Most seasoned entertainers walk in knowing that. Wanda Sykes, somehow, did not get that memo. Sykes talked about naming her fat rolls, and Ziwe noticed that the names sounded like those of white women. When Sykes revealed that one belonged to her late aunt, Ziwe bluntly suggested the aunt was not special. Amy Schumer became another pressure point after Sykes named her among her favorite female comedians. Throughout the interview, Ziwe kept returning to the choice. The interview grew even more awkward when Ziwe asked about Sykes’ wife and children, who are white. Every answer created another trap, and Sykes’ reactions made the tension impossible to miss.

#14: Kevin Hart’s Identity Crisis

From the very first question, Kevin Hart was already behind. Ziwe opened by asking him to state his race, gender, and pronouns, a simple enough request that somehow sent Hart into a prolonged spiral of visible caution. Then Ziwe brought up his 2019 apology video, in which he addressed past homophobic jokes. Ziwe asked, with complete sincerity, how many diamond chains a person should wear in an apology video. Hart walked right into it, answering earnestly before realizing what had just happened. Ziwe kept pressing the contradiction between accountability and image, and Hart repeatedly walked into the setups. Her precision in these moments is surgical, and Hart, despite his quick wit professionally, couldn't find the exit once.

#13: Law Roach Flips the Script

It was Zendaya who reportedly encouraged Law Roach to appear in this interview, and that might have been the messiest thing she's ever done. Roach arrived ready for combat. When Ziwe complimented his signature long black hair and asked to touch it, he immediately redirected the conversation by clapping back about Ziwe's own hair. Then, he revealed he'd worn a leopard-print top specifically to honor Ziwe's Nigerian heritage, a statement so left-field that Ziwe visibly short-circuited. She responded by jokingly demanding he issue a formal apology to the entire nation of Nigeria and all its people. The whole interview played out like two people trying to make each other flinch first. Law Roach mostly won.

#12: Plastic Surgery Consultation

Ziwe takes on the world of plastic surgery by going to the source. In an episode exploring beauty standards, she gets a consultation in the tradition of reality television. Her exchanges with the surgeon are cringe-inducing, from her use of baby talk to her request to have a backside like the one referenced in the Nicki Minaj song “Anaconda.” The peak of the discomfort comes when the surgeon uses an imaging system to scan Ziwe’s face and make hypothetical alterations. In its most uncomfortable moments, the segment illustrates the hypocrisy and pain of conforming to the beauty standard.

#11: Gloria Steinem on “WAP”

It isn’t everyday you hear an iconic feminist speak about “WAP.” When Ziwe interviewed Gloria Steinem, activist and leader of the American second-wave feminist movement, she brought up the Cardi B and Megan Thee Stallion hit. After asking a few questions about whether she believes Karens have a place in the feminist movement and how many Black friends she has, Ziwe turns to pop culture. Although Ziwe reading the explicit lyrics makes for an awkward moment on camera, Steinem actually rounds out the interview with a more balanced take on the song, pointing out that the writer’s intent behind the lyrics needs to be considered.

#10: Phoebe Bridgers ASMR

What does it mean to be an ally? Ziwe wants to get to the bottom of it with her guest, Phoebe Bridgers. She puts the musician on the spot by asking her to read several phrases, ASMR-style. For the entire interview, Phoebe is clearly choosing her words carefully. She is asked to whisper promises to do her own emotional labor and resist the urge to get married on a plantation. She doesn’t give her real PIN, despite Ziwe’s prompting. When she breaks to laugh, the discomfort of the segment is helped by an on-screen message. The tension is broken by the end of the interview, though, as Ziwe and Phoebe move on to smashing ukuleles together in a show of true allyship.

#9: EmRata Talks Empowerment

Ziwe wants to know what empowerment means to model, actress, and writer Emily Ratajkowski. Her answer — she doesn’t know. She admits she had to Google the definition, and offers up a vague statement as her findings. As the interview continues, Ziwe’s ribbing continues to strike lighthearted, yet still cringe-inducing, notes. Although the two are friends in real life and EmRata seems pretty in on the joke, viewers can still tell when Ziwe has her backed into a corner. The model knows her experiences aren’t comparable to Black women in history, and says so. But no matter how hard a guest works, Ziwe’s chyron operator works harder.

#8: Karen Focus Group

The name Karen doesn’t have the best reputation. To prove Karens are real people, Ziwe gathers four for a roundtable discussion about how the slang term makes them feel. The Karens are divided, but the show manages to get several vaguely unsettling soundbites from the participants by the end of the roughly four minute segment. The discomfort of the discussion is elevated by Ziwe’s widened eyes and looks into the camera after each take. She barely has to interject while the Karens bounce off one another. The focus group ends with some custom temporary tattoos and a pledge to be “Karen and proud.”

#7: Ilana Glazer on Climate Change

Global warming has a way of making people feel uncomfortable. In her interview with comedian Ilana Glazer, Ziwe amps up the cringe factor with a line of questioning about the climate crisis. Ilana comes out on the sun’s side, flatly agreeing with Ziwe’s call for an end to life on Earth. At some points, the comedian can be seen visibly squirming in her seat answering questions. The discomfort gets meta when they discuss how Ilana feels during the interview in relation to the looming threat of climate change. It all comes to an awkward head with an unfortunate game and a sad young child. Thankfully, viewers do get confirmation that there was no fracking in the making of “Broad City.”

#6: Eric Adams’ Interview Date

There is uncomfortable, and then there is whatever happened during Eric Adams’ interview. Throughout, the then-New York City mayor directed a steady stream of comments toward Ziwe about her appearance and outfit – comments that sounded like something you'd hear from someone who had seriously misread the room. Adams then pivoted to speaking about his own physique in flattering terms, which visibly made Ziwe bury her face in her hands. When Ziwe deployed her signature extended silence – a tactic designed to make guests squirm – Adams seemed encouraged by it and kept pressing forward. Watching someone mistake deliberate discomfort for heated tension, on camera, in front of an audience, is a specific kind of cringe that doesn't wash off easily.

#5: George Santos’ Controversial Appearance

Many questioned whether convicted fraudster George Santos deserved a platform after his spectacular congressional disgrace. Then the interview aired, and watching him dig deeper became its own form of justice. Ziwe ran through a lineup of civil rights and LGBTQ+ icons – Marsha P. Johnson, James Baldwin, Harvey Milk – asking Santos for his thoughts. His responses strongly suggested he had zero clue who any of them were. Then Ziwe asked him to name fellow congresspeople and identify which ones were frauds. Santos, seemingly unbothered by self-awareness, started naming names without hesitation. The absolute crown jewel of the segment, however, was Ziwe maneuvering Santos into saying “I con” on camera. That alone, made this entire interview i-conic.

#4: Interview with Adam Pally

“Deer in the headlights” doesn’t even begin to describe it. The look on comedian Adam Pally’s face for almost the entirety of his interview with Ziwe shows someone who is partly in on the joke, but mostly scared. Ziwe confronts him with the mistakes of his past, like wearing cornrows for a movie with Robert De Niro. She also makes him perform a monologue from “The Color Purple” and cast a hypothetical Frederick Douglass movie with a cast of white actors. He won’t admit that he is intimidated by her, but his comedic body language and darting eyes betray him until he’s eventually allowed to flee.

#3: Interview with Andrew Yang

Former New York mayoral candidate Andrew Yang stepped into plenty of traps in his interview with Ziwe. The whole exchange is a trip from one cringe-inducing quote to the next. He agrees to talk about ‘true stereotypes’ and even compiles a list. He says his favorite Jay-Z song is the “Numb/Encore” duet with Linkin Park. After being asked about Israel and apartheid, he declines to give a yay or nay opinion. The standout moment comes when he names his favorite subway station — even Ziwe seems to break character to question his answer. At the end of the interview, they each lean in for one final, awkward smile to camera.

#2: Grilling Hannibal Buress

Ziwe starts this interview by demanding a freestyle, and it goes downhill from there. The segment sources its cringe from the fact that comedian Hannibal Buress is a wealthy landlord. After a pointed question about gambling, Hannibal reveals the tactics he used to prepare for the confrontational interview. Unfortunately, his regimen can’t stack up with the reality of being interrogated by Ziwe. He has to put on sunglasses to withstand the discomfort. Even for a seasoned veteran of “The Eric Andre Show” and all of its surreal chaos, the tension on “Ziwe” puts Hannibal on edge.

#1: Chet Hanks’ Accent

Warning: it might take multiple sittings to make it through this interview. Ziwe’s talk with Chet Hanks, son of one of America’s most beloved actors, piles soundbites on top of one another that range from annoying to disturbing. He shares that he isn’t well-versed in the Jamaican Patois he adopted seemingly on a whim. Whether he’s voicing his thoughts on social justice warriors or the origin story behind “white boy summer,” his lack of awareness makes for easy pickings. At some moments, though, even Ziwe seems too stunned to speak in the face of such cringe.

Which moment made you want to hide behind a pillow? Let us know in the comments below!