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Ziwe built a reputation on turning celebrity interviews into cringe comedy gold, and these moments are some of her most painfully funny yet deeply awkward. From evasive answers and social misfires to bold questions that leave guests visibly sweating, this countdown revisits the exchanges that had viewers laughing, gasping, and squirming in equal measure.
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00:00just to clear the air oh to clear the air earlier oh yeah i definitely did not do that for
00:04clout
00:04welcome to ms mojo and today we're counting down our picks for the most notable z-way
00:10interviews and segments that turned awkward exposing or flat-out painful to watch
00:21number 20 whitney levitt interview the interview with whitney levitt star of the secret lives of
00:27mormon wives quickly became an exercise in trying to get a straight answer asked about the first
00:32amendment levitt veered into voting rights prompting z-way to clarify the question um the importance of
00:38the first amendment um it's very important we all have our right to vote and um
00:50yep she also appeared unfamiliar with stop and frisk which z-way also had to explain
00:56whenever the questions got pointed levitt repeatedly suggested she would quote call the press
01:01which sort of became a running joke so if miranda got arrested for exercising her constitutional right
01:07to protest how would you use her your fame i would call up the press i would make sure they
01:13followed
01:13me to go bail her out of jail got it it'd be headlines everywhere got it yeah got it whitney
01:19saves the day then z-way asked how many black friends she had levitt's answer essentially was
01:24not enough leila she's half black got it maybe you after this z-way i don't know that's really good
01:34vibes got it three people wow and that's great so three so yeah we're we're friends the interview
01:42kept circling back to the same awkward problem z-way asked simple questions while levitt struggled
01:48to give simple answers the result was painfully uncomfortable what do i want to say that's catty
01:53oh oh i can't say that
02:05number 19 portia williams and the underground railroad anyone who watched the real housewives of atlanta
02:12remembers the moment portia williams thought the underground railroad was a literal underground
02:16train well there has to be an opening for the railroad at some point because somebody's driving
02:21the train it's not electric like what we have now it wasn't a train maybe it became one of reality
02:29tv's
02:30most infamous clips so naturally z-way brought it back up to her credit williams had clearly done
02:36some homework she explained the railroad mostly accurately this time conceptually what is the
02:42underground railroad well it's a network it's not a real underground it's my actual train and i have
02:47learned that over the years and it's network for what exactly we're moving slaves yeah yeah i understand
02:54it now she even promised she wouldn't say anything ignorant again then immediately seemed to reconsider
03:00that promise in real time things unraveled further when the first amendment came up and williams drew a
03:06blank prompting the show to deliver an impromptu civics lesson on air it's very important i can
03:12tell you oh it is oh i listen i would not be proud to be an american without it oh
03:16yeah yeah and why is
03:18that let me tell you something z-way if you don't know the first amendment then you shouldn't be
03:23protected by it then z-way offered williams the opportunity to say her final words on camera
03:27which she used to throw shade at z-way i just want to say that from black woman to black
03:32woman
03:33i appreciate you you are a light that flickers but you are amazing in your own right and you are
03:43gorgeous where you stand number 18 roy wood jr questions his nepo baby status nepotism sounds a
03:51lot less awkward when you call it a family business and that was the argument comedian roy wood jr
03:56initially made why is it nepotism if the person is rich but like if it's a plumber and it's like
04:02jimmy and sons plumbing no one no one gives a f*** that jimmy and his sons are in fact you
04:09would
04:09rather it yeah you'd rather nepotism during his z-way interview he defended passing resources and
04:15connections through generations comparing it to a family-owned restaurant then z-way pointed out that
04:21wood's father roy wood senior was a prominent civil rights journalist who helped establish a path in
04:26american journalism no it makes sense that you as also a nepo baby would come out in defense of nepo
04:31babies am i a nepo baby i mean your father paved the way in american journalism okay all right you're
04:38fine but my dad didn't give me no hook up on that though like well wood pushed back saying his
04:43father
04:44never simply handed him a career but then he stumbled on the realization that he actually started at the
04:49same radio station where his father had worked that seemed to stir up a minor existential crisis
04:54for the comedian i started at the same radio station my father started you did are you serious
05:00yeah but my father no that's excuse me my pops let me say it like that when you say pops
05:06it don't
05:06sound nepotistic number 17 vince staples musings the thing about vince staples is that his voice is so
05:13measured and calm that you almost trust whatever he's about to say almost autism that's just life
05:19man it's creativity we're selfish as human beings we want mozart but we don't want a little drool here
05:25and there what's wrong during his z-way interview staples delivered some genuinely unhinged takes with
05:33the energy of someone reading a grocery list asked to weigh in on what had caused more harm to the
05:38black
05:38community drugs or processed sugar staples bypassed both options entirely and threw his own jar of music
05:44under the bus and so is this an anti-hip-hop and rap psa no not as long as i'm
05:51doing it got it but
05:52know you're selling the poison later z-way asked which white people he would invite to the cookout
05:59staples sidestepped the premise and launched into a rant about homelessness he also did well to mention
06:05how exactly he supports his friends who are unhoused i give them money for their drugs
06:12for their drugs come on i'm hungry for black tar heroin vince things are about to get even more
06:22uncomfortable but at least the mizmojo 24 7 live stream is always a safe space scan the qr code on
06:28your screen to join for non-stop entertainment i think it's good that you're giving back to your
06:32community i don't know so long i want it back for sure number 16 jabuki young white's draft evasion
06:41strategy now lavender marriage would you ever 100 i honestly maybe would prefer that and who would you
06:47marry kristen stewart she gave this talk recently about like the state of film and i was like that's so
06:54hot you like when women wax poetically about a dying industry i'm into that jabuki young white
07:00brought the kind of chaotic comic energy that makes a z-way interview dangerous after discussing
07:05an awkward sephora encounter z-way asked him to demonstrate how he had walked into the store
07:09his exaggerated performance prompted z-way to call it a quote deeply offensive portrayal and how did you
07:16walk into the store like this hello sephora employees i'm here for a fierce cover-up you see
07:25these eye bags i need them covered up and that's sort of it the conversation then moved to a hypothetical
07:33military draft asked how he would avoid serving jabuki proposed leaning hard into his gayness and
07:39demonstrated what that strategy might look like his commitment paired with z-way straight face made
07:45every second more absurd it would be crazy if i had to do something to get into the military sergeant
07:55oh oh it's mighty hot in here sergeant is it okay if i take this off it was hilarious but
08:02also
08:02the kind of exchange that makes you wonder whether you should be laughing at all when do i get to
08:06meet
08:06the other troops and that's how you dodge the draft uh-huh number 15 wanda sykes takes every single
08:19piece of bait z-way's entire interview style is essentially an elaborate trap most seasoned entertainers
08:26walk in knowing that wanda sykes somehow did not get that memo you know he apologized he did he did
08:33eventually he did apologize do you forgive him of course okay of course and we love that in the black
08:40community because no one wins when the family feuds right exactly sykes talked about naming her fat
08:46roles and z-way noticed that the name sounded like those of white women when sykes revealed that
08:51one belonged to her late aunt z-way bluntly suggested the ant was not special you didn't
08:56say you're putting down you're putting down my aunt who's passed away one of my you know favorite
09:00aunts now you really really why don't we all die your aunt's not special
09:09you're nuts you know that amy schumer became another pressure point after sykes named her among
09:15her favorite female comedians throughout the interview z-way kept returning to the choice
09:20you refused to name five black friends but you're you rushed to name amy schumer oh wow
09:28okay oh i have one amy schumer okay it fell out of your mouth amy schumer did i say amy
09:34schumer
09:34so five black friends you don't have the time for the interview grew even more awkward when z-way
09:42asked about sykes's wife and children who are white every answer created another trap and sykes's reactions
09:48made the tension impossible to miss should we unpack the fact that you're the only black person in
09:53your nuclear family we can do that i take care of white people that's what i do all right is
10:02that
10:02what you want me to say z-way is that it number 14 kevin hart's identity crisis from the very
10:08first
10:09question kevin hart was already behind z-way opened by asking him to state his race gender and pronouns
10:15a simple enough request that somehow sent hart into a prolonged spiral of visible caution like
10:21what is the correct way i okay thou uh am i black you tell me kevin that's what i'm saying
10:30i don't know
10:30what's right anymore this is not a trick question then z-way brought up his 2019 apology video in which
10:38he addressed past homophobic jokes z-way asked with complete sincerity how many diamond chains a person
10:44should wear in an apology video hart walked right into it answering earnestly before realizing what
10:50had just happened and how many diamond chains should one wear in a front-facing apology video
10:55well if it's the right source of diamond chain you only need one because the quality should
11:02none are you flexing on these brokies at home z-way kept pressing the contradiction between
11:08accountability and image and hart repeatedly walked into the setups her precision in these moments is
11:14surgical and hart despite his quick wit professionally couldn't find the exit once what's your favorite
11:20letter in lgbtqia the definition of it and what is the definition the fact that you would want me to
11:29answer that says a lot about you it says a lot about you number 13 la roach flips the script
11:36what's your
11:37favorite celine dion song my favorite i mean my heart would go on oh yeah just like my career
11:45i wish i could say the same for yours
11:51it was zendaya who reportedly encouraged la roach to appear in this interview and that might have been
11:56the messiest thing she's ever done roach arrived ready for combat when z-way complimented his signature
12:02long black hair and asked to touch it he immediately redirected the conversation by clapping back about
12:07z-way's own hair oh my gosh like jimmy fallon oh my gosh wow yeah now let me touch yours
12:14okay
12:16totally different feeling
12:21oh you want to play then he revealed he had worn a leopard print top specifically to honor z-way's
12:28nigerian heritage a statement so left field that z-way visibly short-circuited she responded by
12:34jokingly demanding he issue a formal apology to the entire nation of nigeria and all its people
12:40i apologize nigeria because i thought that this print represented your culture
12:47and the animals that you keep in your homes sorry nigeria the whole interview played out like
12:56two people trying to make each other flinch first la roach mostly one i thought i was paying homage
13:02the fact that you assume that all nigerians have a leopard in their house is crazy what do you have
13:08in your house a kitchen oh number 12 plastic surgery consultation z-way takes on the world of plastic
13:16surgery by going to the source in an episode exploring beauty standards she gets a consultation
13:22in the tradition of reality television and you look even more hot than you are now you look like
13:27a supermodel her exchanges with the surgeon are cringe inducing from her use of baby talk to her
13:33request to have a backside like the one referenced in the nikki minaj song anaconda i want to like a
13:39big
13:39fat ass like nikki minaj she has this line she goes big fat ass the peak of the discomfort comes
13:46when
13:46the surgeon uses an imaging system to scan z-way's face and make hypothetical alterations in its most
13:52uncomfortable moments the segment illustrates the hypocrisy and pain of conforming to the beauty
13:57standard looks like you but better i guess me but better i don't think there is a better but i
14:03really
14:03no me no no me but better no number 11 gloria steinam on wap it isn't every day that you
14:11hear an
14:11iconic feminist speak about wap when z-way interviewed gloria steinam activist and leader
14:16of the american second wave feminist movement she brought up the cardi b and megan the stallion hit
14:21have you ever heard the song called wap by cardi b and megan the stallion yes no i haven't after
14:26asking a few questions about whether she believes karens have a place in the feminist movement and how
14:31many black friends she has z-way turns to pop culture there's some in this house there's some in this
14:37house although z-way reading the explicit lyrics makes for an awkward moment on camera steinam
14:42actually rounds out the interview with a more balanced take on the song pointing out that the
14:47writer's intent behind the lyrics needs to be considered do you feel empowered as a lady no no
14:54no but it but it depends who wrote it number 10 phoebe bridgers asmr what does it mean to be
15:01an ally
15:02z-way wants to get to the bottom of it with her guest phoebe bridgers she puts the musician on
15:07the
15:07spot by asking her to read several phrases asmr style i will do my own emotional labor i apologize
15:15for all racism for the entire interview phoebe is clearly choosing her words carefully she's asked to
15:23whisper promises to do her own emotional labor and resist the urge to get married on a plantation
15:27she doesn't give her real pin despite z-way's prompting no you're supposed to say the number
15:34six six six six when she breaks to laugh the discomfort of the segment is helped by an on-screen
15:40message i'm not gonna read that one
15:46uh wow the tension is broken by the end of the interview though as z-way and phoebe move on
15:53to
15:53smashing ukuleles together in a show of true allyship okay oh my god oh my god easy see harder
16:01oh my god
16:05number nine emrata talks empowerment z-way wants to know what empowerment means to model actress and
16:11writer emily radakowski her answer she doesn't know she admits she had to google the definition
16:17of empowerment and offers up a vague statement as to her findings so what exactly does empowerment
16:22means to you i don't know what empowerment means i had to google the definition of empowerment as
16:28the interview goes on z-way's ribbing continues to strike light-hearted yet still cringe inducing
16:34notes although the two are friends in real life and emrata seems pretty in on the joke viewers can
16:39still tell when z-way has her backed into a corner i'm sorry i guess i'm not a good friend
16:43i guess not the model knows her experiences aren't comparable to black women in history
16:48and says so but no matter how hard a guest works z-way's chyron operator works harder we um
16:55both empower women to make things and make money and build brands and you know do that kind of stuff
17:06number eight karen focus group the name karen doesn't have the best reputation
17:12to prove karens are real people z-way gathers four for a roundtable discussion about how the
17:18slang term makes them feel the karens are divided but the show manages to get several vaguely unsettling
17:24sound bites from the participants by the end of the roughly four minute segment do you think karen's
17:29lives matter i think that karen's lives matter because if karen's lives don't matter no lives matter
17:37the discomfort of the discussion is elevated by z-way's widened eyes and looks into the camera
17:42after each take i find it offending because her name isn't karen right so now we're being racist
17:49she barely has to interject while the karens bounce off one another the focus group ends with
17:55some custom temporary tattoos and a pledge to be karen and proud
17:59karen and proud number seven elana glazer on climate change climate change has a way of
18:07making people feel uncomfortable in her interview with comedian elana glazer z-way amps up the cringe
18:13factor with a line of questioning about the climate crisis elana comes out on the sun's side flatly
18:18agreeing with z-way's call for an end to life on earth death to all earthlings yeah at some points
18:25the comedian can be seen visibly squirming in her seat answering questions the discomfort gets meta
18:31when they discuss how elana feels during the interview in relation to the looming threat of
18:35climate change i'm yeah like painfully uncomfortable like now very much like now it all comes to an
18:44awkward head with an unfortunate game and a sad young child thankfully viewers do get confirmation that
18:51there was no fracking in the making of broad city clearly our production didn't frack but were we
18:57shooting on fracked land probably number six eric adams interview date every stop is the right stop
19:04if it's used correctly because when you're on the train with that beautiful outfit you have on thank you
19:10and all of a sudden you see someone hanging out there hanging out there and they have a bulge on
19:14their
19:14side and not the bulge that others would talk about oh wow there is uncomfortable and then there is
19:20whatever happened during eric adams interview throughout the then new york city mayor directed
19:26a steady stream of comments towards z-way about her appearance and outfit comments that sounded
19:30like something you'd hear from someone who had seriously misread the room you want to look like
19:35this and you're gonna have somebody walking down the block with you keep referring to my appearance
19:39i can't you you took time to dress up to look nice you know as well as i do you
19:44appreciate the fact that
19:46i'm acknowledging how well you are put together let's change the subject adams then pivoted to
19:52speaking about his own physique in flattering terms which visibly made z-way bury her face in her hands
19:57when i get out of the shower and take a look at myself and my six packs and the firmness
20:02of my body
20:03i'm living the 65 life if you'd like to show your six pack please when z-way deployed her signature
20:11extended silence a tactic designed to make guests squirm adam seemed encouraged by it and kept
20:17pressing forward watching someone mistake deliberate discomfort for heated tension on camera in front
20:23of an audience is a specific kind of cringe that doesn't wash off easily you know i don't think
20:32people realize what's in a person's eyes oh gosh number five george santos's controversial appearance
20:40rosa parks believe it or not is one of my favorite political figures why wouldn't i believe that
20:45i had a portrait of her in my office i think that speaks for itself how else are you like
20:50rosa parks
20:51i i used an analogy i'm not like rosa parks come on many questioned whether convicted fraudster
20:58george santos deserved a platform after his spectacular congressional disgrace then the
21:03interview aired and watching him dig deeper became its own form of justice z-way ran through a lineup of
21:10civil rights and lgbtqia plus icons marcia p johnson james baldwin harvey milk asking santos for his thoughts
21:17his responses strongly suggested he had zero clue who any of them were james baldwin huh james baldwin
21:25who the hell is james baldwin who's james baldwin harvey milk i have no clue who that is okay what
21:34about bowen yang doing an impression of you on snl i think he deserves an egot then z-way asked
21:40him to
21:40name fellow congresspeople and identify which ones were frauds santos seemingly unbothered by self-awareness
21:47started naming names without hesitation dan goldman he doesn't pay his rent dan good dan
21:54dan is owing 180 000 worth of rent right now on his 45 000 monthly rent which is what most
22:02americans
22:03make a year the absolute crown jewel of the segment however was z-way maneuvering santos into saying
22:09icon on camera that alone made this interview iconic can you also say that you're an icon i know you're
22:17the
22:17icon no you're no you icon you're iconic icon icon girl girl boss don't say icon again icon you con
22:26number four interview with adam pally deer in the headlights doesn't even begin to describe it
22:32the look on comedian adam pally's face for almost the entirety of his interview with z-way shows someone
22:38who is partly in on the joke but mostly scared z-way confronts him with the mistakes of his past
22:44like
22:45wearing cornrows for a movie with robert de niro was it worth it absolutely not nothing nothing
22:51i've ever done was worth that she also makes him perform a monologue from the color purple
22:55and cast a hypothetical frederick douglas movie with a cast of white actors this game is very hard
23:03i feel like i shouldn't be playing it he won't admit that he's intimidated by her but his comedic body
23:10language and darting eyes betray him until he's eventually allowed to flee do i intimidate you
23:15adam no no i like i like being with you number three interview with andrew yang former new york
23:22mayoral candidate andrew yang stepped into plenty of traps in his interview with z-way the whole
23:27exchange is a trip from one cringe inducing quote to the next he agrees to talk about true stereotypes
23:34and even compiles a list he says his favorite jay-z song is the numb and encore duet with lincoln
23:40park
23:41can i get an encore do you want more but it was like that was uh him and i think
23:46it was a duet right
23:47after being asked about israel and apartheid he declines to give a yay or nay opinion again i just
23:54want peace in the region i'd like so many other new yorkers and other people around the world the standout
23:58moment comes when he names his favorite subway station even z-way seems to break character to
24:03question his answer okay what's your favorite subway station
24:08it's my stop so time square i've been in your favorite subway station is time square
24:13at the end of the interview they each lean in for one final awkward smile to camera
24:19number two grilling hannibal burris z-way starts this interview by demanding a freestyle and it all
24:26goes downhill from there feeling real calm got it adderall coursing through my veins okay shout out
24:32the segment sources its cringe from the fact that comedian hannibal burris is a wealthy landlord
24:38after a pointed question about gambling hannibal reveals the tactics he used to prepare for the
24:43confrontational interview to prepare for this i rented a soundstage and had five women sort of look
24:52like you just uh say passive aggressive things to me unfortunately his regimen cannot stack up with
24:58the reality of being interrogated by z-way he has to put on sunglasses to withstand the discomfort
25:04even for a seasoned veteran of the eric andre show and all of its surreal chaos the tension on z
25:10-way
25:10puts hannibal on edge that's actually literally not how buildings work really really number one chet hanks's
25:18accent warning it might take multiple sittings to make it through this interview z-way's talk with
25:24chet hanks son of one of america's most beloved actors piles sound bites on top of one another that
25:30range from annoying to disturbing he shares that he isn't well versed in the jamaican patois he adopted
25:37seemingly on a whim a couple two tree tigs whether he's voicing his thoughts on social justice warriors
25:45or the origin story behind white boy summer his lack of awareness makes for easy pickings can you tell
25:51us how that's different from the past 400 summers in american history i guess not i don't know at some
26:00moments though even z-way seems too stunned to speak in the face of such cringe hashtag cheddars
26:09which moment made you want to hide behind a pillow let us know in the comments