Ziwe’s Most Uncomfortable Interviews

Late-night sensation Ziwe Fumudoh is about to close out the second season of her hit Showtime talk show, Ziwe. The host made a name for herself by strategically entrapping her guests into admitting their biases about race, gender, and politics. Despite asking hard-hitting and blunt questions, she maintains a satirical and comedic tone throughout, all while wearing television’s best outfits. Because Ziwe doesn’t shy away from what many would consider taboo subjects, her guests are often stumped and unable to craft an intelligible answer. Those moments make for some of the most cringe-worthy interviews in talk show history. Out of the eighteen iconic episodes of Ziwe, here are the conversations that were so awkward we almost had to change the channel.

Michael Che

Recently on her show, Ziwe had SNL head writer and weekend update anchor Michael Che in the hot seat. She hardly poses a single question before he was stumbling over his words, fidgeting in discomfort, and trying to deflect with humor. No-nonsense Ziwe notices this and hits him with, “Do you usually patronize women like this or am I special?” He stutters before his defense (despite being a professional writer) is that he doesn’t even know what patronizing means. This is all followed by a painfully long-drawn-out silence that is only ended by Che needing to fill the room with his voice. Ziwe’s segment proved that Che’s the type of comedian that loves to dish it out but just can’t take it.

RELATED: Ziwe’s Confrontational Comedy is the Perfect Way to Challenge White Privilege

Phoebe Bridgers

In the early episodes of Ziwe, adored indie singer-songwriter Phoebe Bridgers made an appearance on the show. Though she’s an outspoken liberal and activist, the power of Ziwe is still able to trip Bridgers up. In a role play segment, Bridgers acts out a call to 911 to report that Ziwe has stabbed her. When the operator asks her to describe the assailant’s race, Phoebe states that she is Black. The show immediately turns into a musical number called ‘Phoebe Calls the Cops on Black People.’ The next segment is the singer reading out sentences like, “I will never get married in a plantation,” in ASMR style. After getting through a couple, Bridgers refuses to read the rest. A classic Ziwe awkward silence concludes the interview before they both smash ukuleles.

Chet Hanks

In this recipe for disaster, internet provocateur and nepotism baby Chet Hanks joined Ziwe for a hilariously uncomfortable interview. His appearance was in light of him randomly using a Patois accent and trying to instigate the movement ‘White Boy Summer’. While the idea of her whole show is to make her guests stir in discomfort, Hanks actually manages to make Ziwe uncomfortable by switching in between his normal and Jamaican dialects, freestyle rapping about having a three-way with her, and doing an unhinged Joker impression. His blissful ignorance actually makes Hanks immune to embarrassment, and he proudly takes her bait by repeating “social justice warriors can kick rocks.”

Andrew Yang

Ziwe doesn’t just invite pop culture figures on her show. One of her first interviews was with politician Andrew Yang during his bid for New York mayor, so it was likely an effort to appeal to young voters. His desire to be hip crashed and burned when he claimed that Jay-Z was his favourite rapper, then Ziwe asked what his favourite song was. Panic washed all over his face, and in typical politician fashion, he stalled answering by just repeating the question as if he was deep in thought. After a few beats, he raps a couple of lines of “Encore,” one of the most well-known songs by Jay-Z. Digging the hole even deeper, he goes on to name the rapper’s collaboration with Kanye West that he decided just to call “Bleep Word in Paris.” He should have stopped at “Encore.”

Fran Lebowitz

Author and New York legend Fran Lebowitz admittedly had no idea where she was or who she was with on the inaugural episode of Ziwe. The host immediately calls her out for trying to control the process of the show by refusing to do a walk-out introduction or play any games, “Is that standard for white women to come on a show and dictate how it’s supposed to go?” Lebowitz is known for her intellectual stoicism and social commentary, so she fires back with, “Only black women think white women are in charge of things.” Ziwe’s generation Z, modern politics mixed with Lebowitz’s old-fashioned, somewhat centrist views make for a perfectly engaging yet hard-to-watch interview.

Hannibal Buress

You’d think that Ziwe chatting with Hannibal Buress would be a simple one. They both have similar dead-pan comedy styles and understand the nuance of satire. However, Buress was clearly a little out of his comfort zone right off the bat. Like Michael Che, he started squirming a bit, and tried to make some jokes but essentially just wanted to deflect. He called her questions passive-aggressive and then put on sunglasses because he was “intimidated by the environment.” The best part of the segment is Ziwe’s utterly perplexed reactions to Buress’ behavior and calling him out on being a landlord.

Adam Pally

Last but certainly not least is one of the most uncomfortable interviews from the show. Comedic actor Adam Pally sat down and was immediately faced with a photo of him in cornrows. Rather than the defensive stance, Pally took the role of submissive. It was a wise choice on his behalf to just agree and echo anything Ziwe said. In the next segment, Ziwe gave Pally the task of reading out a monologue from The Color Purple. Agreeable Pally stuttered through the lines while looking to the camera crew for help. In many ways, Pally is the perfect guest for Ziwe. First, he’s a white man, but he’s also so passive that you can’t help but cringe when watching him fold under pressure.

If you can handle it, all of these awkward moments from Ziwe are available to watch on Showtime.