Five Cringe Moments in the Career of Kanye West

Hey, y'all, thanks for tuning in to Cue Points. Before you take in this show, we want to acknowledge and stress that neither DJ Sir Daniel or Jay Ray support Ye's many anti black, anti Semitic and downright problematic behavior and comments that he's made over the course of his career in any way, shape or form, in fact, condemn this behavior. This show is meant as an examination of how we got to this point with Yay. Our thoughts on his legacy and some entertainment, nothing more. Enjoy the show.

Greetings. Welcome to another episode of Q Points podcast. I'm DJ Sir Daniel and my name.

Is Jay Ray, sometimes known by my government as Johnny Ray Kornegay iii. And unlike the person that we're going to talk about today, my name is the name that I was given at birth.

Well, okay, but let's just get to it, J Ray. There was a time. There was a time in hip hop history. Yes, kids, gather around. There was a time in hip hop history in the last century when there was a by the name of Kanye west that, you know, with his backpack and his bright polos and his clever rhymes used to bring us so much joy. And he was a bright and happy presence in hip hop, J Ray.

Yes.

But now in 2025, the mere mention of his name elicits size and heavy groans aside.

What.

What he do now, now. So, I mean, so for this episode, J Ray, we want to discuss, like, the cringiest moments that Kanye has given to us. I feel like he's given us more cringy hits than hit records.

Yeah. And what's the interesting thing about talking about ye in 2025 is that this pattern really started 20 years ago. So this is a very well seasoned pattern of behavior that. And I know that we'll talk about this later as we get into kind of the mental health of it all, but I think one of the things that we do. So this is me indicting us as, like, fans, is that this is the kind of stuff we like. We want people to grind, we want people to go against the grain, we want people to do all of the things, but we don't always recognize what that is and the cost of that thing. And I think that if we were paying attention in 2005 and in 2009, we would have said, get that man some help.

I'mma let me finish. And then, Jay Ray, you go ahead and start with the first one. The first cringiest moment of Kanye's history.

Yeah, yeah. I think the first one that we can pinpoint as a Cringy moment is, you know, the Hurricane Katrina broadcast, which we don't have to describe in too much detail on this, but what generally happened is there was a benefit for folks impacted by Hurricane Katrina, which for. What's crazy in 2025 to think about how big a deal that was when now there's been so many of these types. Things or natural disasters around the country, but in 2005, this was like, oh, my God, what? But. So there was a benefit, and there is yay up there with Mike Myers. Mike Myers was once a huge star, y'all. Just to keep in mind, we haven't seen him in forever.

He was big. Huge. He was Austin Powers.

He was Powers. So. And then Kanye did the George Bush doesn't care about black people thing. Now, what was crazy about that? So, see, here's how we, as fans, like, let that go. Be like, I mean, yeah.

Oh, you rocked with it. We loved it.

Yeah. That's a thing, Right?

You know what I mean?

Get him, Kanye. Tell him, Kanye. Right? So it was kind of one of those moments I do remember as a community, we were just kind of like, oh, that's so cool that he said that right there. Right there on national tv, on a benefit, Right?

And so he's him. As the young people say today. He's him. He's him. He's a revolutionary. A revolutionary. We. I mean, whatever label that the black community had, we were putting it on him. He is the next coming of Tupac. He is. He is the New Black Panther movement. He is. He is Wakanda Forever. Before we even knew about Wakanda Forever. He's all of those things.

Yeah, he's.

And he's. And he's lifted up because he's also surrounded by black excellence. You know, terms that we were using heavily back then. He was surrounded by black excellence. He was surrounded by, you know, all the tastemakers and the fashion designers, and everybody wanted to be around him. He's got the hottest chick in the game on his arm. Kanye was the. Was it. And I guess especially for a lot of young black men, he was just somebody to. To look at and to aspire to. And, you know, I mean, for some. Let's be real, he was somebody.

No, he wasn't. No, no, no, no, no. I'm agreeing. I'm agreeing. That side was more of a. Ooh. We have to recognize the signs. You know what I mean?

We weren't looking.

We weren't looking. And recognizing that stuff can be two things, right? Like that thing that he Said can be very much like, yeah, I definitely do that. And also recognize that I probably wouldn't have said that right there. Like, I probably wouldn't have said that right there. For a lot of reasons. Right? For a lot of reasons. It's not because I'm standing next to Mike Myers. It's not because it's on national tv. It's probably because we need to make sure that these people in New Orleans get what they need. You know what I'm saying? I don't need this moment to be about my foolishness now. I would have came right back out and been like, here's what I wanted to say. I didn't say that there because I needed these checks to keep flowing now. So saying all that to say, I know I don't wanna spend a ton of time on that, but that was absolutely the first glimmer of, like, for the world, this was like, for the world, this was a glimmer of cringe. And I think for black folks was like, yeah, more of that. And then we got more of that.

And then we got more. Yeah. It's hearkening back to what you said about what his mom said. My son could be self absorbed.

Yes.

And so what. What we're seeing now is that what we're starting to question is the. The motive behind things, the motivation. Is your motivation really about calling speaking truth to power, or was this a viral moment before we knew what viral was? Yes, this is a viral moment because we. I need it to be about me and what I'm thinking right now. Whatever, what I'm. What's going on up here has to come out. And you. Which is a disorder. Yeah, yeah, yeah, There's. That filter is not there. And we found out that in that moment. And then things progressed because one bottle of Hennessy changed the life of everybody at the MTV Music Awards in 2009. Specifically Beyonce. Yeah, Beyonce. What made that moment super cringy. And of course, I'm talking about the imma let you finish Taylor Swift moment, was he got up there again, questioning his motivation. He says, he said, I'm doing this because I believe Beyonce should have won over you, Taylor Swift, but go ahead and accept your little award.

Right?

But he got up there and made it about him.

Yes.

Even Beyonce was mortified. She was mortified in that moment.

That's why she went back in the house. That's why she went in the house. Beyonce was like, you know what? I'm not even coming out no more. That was a rough night for Beyonce. I'm not even coming out no more. Oh, yeah.

Cause that was the same night that Beyonce, with all her strength, tried to keep Lil Mama off that stage.

Exact same. Beyonce was like, you know what? Y'all got it.

No, don't go up there.

Y'all got it.

You know what? I didn't think about that. You're absolutely right. From that moment on, she was like, you know what? I'm not hitting up these award shows like I used to. And it again. What made. Again, to reiterate, what made that moment of cringe suspect was because now we're really starting to see a pattern. When he could have talked to. Hopped on the Breakfast Club the next morning.

Absolutely.

Sway, he could have gotten on his Twitter. He could have used his Twitter fingers and made that same comment about thinking that Beyonce should have won.

Yes.

But he got up there because knowing all cameras were going to be focused on him. Any bottle in. In hand.

Yep.

I'm gonna let you finish. Go ahead. So we have that moment in time.

This is a very interesting moment because I also think it foreshadowed Kanye's allegiance. Right. So this particular moment. So this is like, what, 2012, 2013. Kanye is being interviewed on Sway, and he is on the precipice of the Yeezy, you know, the Yeezys, like, dropping this brand, blah, blah, blah. And of course, Kanye, Ye is going, big brand connections, all of that. And so Sway, very astutely, as being like, black man, big brother, is very much like, well, why does it have to be this way? Because, you know, Ye was, of course, talking about how to, you know, sell this brand to customers. But there was all of this back and forth is, you know, the Adidas. So there was a big conversation. And so anyway, Kanye was kind of scoffing at Sway's suggestion to empower himself to kind of like, hey, you don't. You don't need these big brands. And then it became the you. You don't have the answer, Sway. You ain't got the answer, Sway. House. And it was the House way. You ain't got the answer.

He was literally. He was literally barking at that man. House way, right? What we. J. What we saw in that moment is what we. We saw a. A ramping up in real time. We saw him. His emotions. He became. He started spiraling, and he started ramping up in his. His emotions, and. And he started to become. He started to lose his ability to regulate himself, and he became dysregulated really quickly to the point where he started barking as Sway.

And you're like, this is Sway. This is way. And. And Sway to that point was really trying to be positive about. Like, listen, these are things that you can do. Like, you can. You know, you. You don't have. You don't need all of this other stuff. Like, you could not. Trying to have it. So I think this was also another moment of we get to see, like, no, this is. This is how this person sees themselves, how they see themselves in the world, how they see who's powerful. Right.

And it was the value that they associate.

Yes.

The value that he associates with name brands, clothing brands. Let's just say it. Whiteness.

Whiteness. Yes.

The. The value that he placed on that and how. And how it will work for him.

Yeah.

How it will elevate him was very, very important to him in that moment. And he just couldn't understand why Sway could not see that. And. But I think the. The most important part of that interaction and the best part of that interaction was that sway in a loving but very firm black man to black man. Like, hey, I don't know who you talking to right now, but you need to bring it down.

Down, Right? Yes, you.

I'm a man, just like you're a man. You are not gonna come on my show and talk to me.

My show.

No, we can agree to disagree, but this right here, this kind of interaction is not going to happen. And it was like he needed that moment because God knows how many people are telling him yes when they tell him, when they need to tell him.

No, no, a lot more. No, he needs a lot more no's.

He needed a lot more no's. And this black man who love him and has his own platform, but he's not. He's not as I guess you would. You know what, Bump that. Sway is as huge a star as Kanye is.

Yeah, he's an icon.

Yeah, he's an icon. He's a recording artist, radio, television. He's been on MTV for all of our lives. Sway is just as much as important to the culture as Kanye was.

Absolutely.

He let. He reminded him in that moment. And you can never tell me anything about Sway after that. Another moment where a black man, another black man, had to remind him because there was a lot at stake. There was a lot going on at stake in the world. We were on the precipice of the first 45 administration, and all of us as a country were in a panic. But here comes Kanye spewing all kinds of. Of nonsense, rocking the MAGA hat and you know, shout out to Van Lathan. Van Lathan was just recently on the Tory Park Tory show with Tory. And, you know, Van Lathan is a. I respect dude a lot that he was at. During his stint at tmz. He was, you know, he was there as one of the reporters, and he was, you know, giving his two cents on any of the matters that were coming up at the time. But, Lord, they had Kanye live in studio after Kanye had been going across the country just talking pure recklessness.

Pure recklessness. And I think this is also. I don't think that the media had caught up or any of us had caught up to just how bad it had gotten. And. And that's probably because ye would always have outbursts, and it'd be like, oh, he had an outburst. But, oh, here's the change. This is. This is. This is when we started to figure this out. He would have the outburst, but then that music would be hot. What started to happen was, oh, you're having an outburst, and this music ain't even hitting. Like, dude, you can't do both.

You not holding up your end of the bargain.

You not holding up your end of the bargain. Like, you sure this is America First First Amendment. You can have all of the free speech you want, but this music needs to be. Be hidden. And it's not.

You ain't got no gold digger, right?

You ain't got no gold digger in your Serrato. Listen. So that moment so specifically when Kanye. When Van completely lost it was Kanye literally said out of his mouth, a black man said that slavery was a choice. And I think the collective. Every Gen Xer and older millennial, because I realized that we have, like, there was some age stuff in terms of people how start. People start to respond. But we was given a, oh, hell nah, we don't do this. We're all in front of all of these white folks on national tv.

Rocking the MAGA hat, too.

And rocking the mag. I think he was. I think he was. I don't think he had gotten to the MAGA hat yet. I think the MAGA hat came later. But if he had the MAGA hat, y'all let us know in the description. But, yo, Sir Daniel, I specifically, I. There was a collective national black. No, this one can't do that.

At all. So, no, you're correct. He did not have on the MAGA hat in that TMZ moment. But you are. And you are also correct that collectively, we couldn't believe our ears. Collectively, we thought we. We just knew we had Lost this brother.

Oh, you can't.

Like, we gotta. We gotta get rid of all.

We gotta, like, cancel for real Kanye. Like, we gotta really cancel him.

And I think this was like, when cancel cancel culture. The term cancel culture became part of our lexicon. And we started, you know, using that, especially because he was heavy on Twitter. You know, he was. He was aligning himself with prep with 45 at the time. And he was just making all these erroneous statements. He was talking about Harriet Tubman. Harry ain't Harriet Tubman ain't never hurt you.

Harriet Tubman ain't never hurt you. And wouldn't have. Now homegirl would've had to leave you where you was at. And I think I will say that what was crazy for me, because I definitely got. Oh, no. I had been off the Kanye train for a minute, but I think it was easy for me to accept that decision. Now. What I found disturbing was how so many folks, people I know who are smart black folks, started to debate this point. And I'm like, you're like a smart person. But they were gonna ride with their Kanye and they were gonna debate. I understand where Kanye was coming from, really, because this was around the same time, too, when that crazy ass shirt started coming out. Where I am not. Was it the. I am not my ancestors. This is. I think this. This is a very similar time frame and where we had to get together and was like, baby, you certainly are not, because you ain't getting none of the stuff that they got done done. You are not them.

You told me not that. But you know what, Jay? When I think about it, and it's. I don't think it's any coincidence that all of these things happen at the same time. We. We were witnessing the radical. Is. We witnessed the radicalization of Kanye West. Right. And the weaponization of his celebrity.

Yes.

And so what that incoming administration sought out to do, they needed somebody to do. To do the heavy lifting for them.

Right.

And he. Little did he know, he volunteered himself for that, for that.

Put on red hat.

He was ready for it. Because again, they recognized. They probably saw. There's probably somebody that did a psychological profile on that young man. And I saw that he's got. He's got definite. He fits a profile of somebody who has lofty images of himself or lofty ideas about himself and things that aren't necessarily realistic. And they saw all of that, and they pinpointed it. They already knew, well, oh, what he likes. He wants to be. He wants to associate himself with whiteness he wants to align himself with whiteness. And so that's what we're going to do, is we're going to offer him whiteness and all the, the, the fringe benefits that come with whiteness. And he's going to be having the time in his life where he doesn't even remember the west side of Chicago. He doesn't remember that life. And so he's just going to, whenever he gets a chance, we're going to let him loose so he can do. He can do what damage he does, and we're just going to yank him back when we're ready. But it's. I think, yeah, I think we, we witnessed it. We did witnessed the radicalization of Kanye West's undiagnosed psychosis and his genius. They got him thinking. Remember when they thought. Got him to thinking that he could run for president in 2020. And it was such a pivotal time in that election. It was so late in the election, and we were already, as a country like, look, we don't need anybody coming in here rocking this boat, because we're all on the same page that we got to get him. We got to get 45 out of there.

Right?

We got to get 45 out of there. But what always happens is there's a divisive. There's always. What do they call those people who will go into the cointelpro, the people that. Into the, the freedom movements of the civil rights era, and they would spy and cause dissension.

Yes.

Report back. We had a real life COINTELPRO moment with Kanye west in 2020 when he decided he wanted to run for president with the bulletproof vests and calling press conferences and these weird, rambling, staged press conferences where he would come out. Is this when he was wearing the, the pooh shies and the, the masks covering himself?

No, this is, this is, this is prior to that, because I think that started to come. That started to come later because, you know, he started to devolve a, um. That was super cringe. The Kanye for president was cringe and weird. And you know what? This, this goes back to the man love a spotlight. The man ain't never met a spotlight that he don't like. And there's a time and a place for that. I get, I get in order to be. To command stages and to do all of these things as big as he does them, that's kind of the personality you have to have. But you also need people in your life that's like, you know what? Sit down. This is a Mess. You're being a mess. Actually, more than that. Well, let's get you some help. Let's get you into this doctor's office, please, and sit you down and get you what you need. I don't know what it is that you need, but you need something and you don't need to do this because watching him do them press conferences was tragic.

Here's the thing that really gets me, and I know people went up for it and they loved it, was when he came back with a 100 piece gospel choir behind him and a key banging away on a keyboard that was probably not even turned on and was giving y'all trap gospel and y'all were.

Just eating that stuff, that shit up. Listen, of all of the things that made me so angry because I'm like y'all. And what I know is he was going to these different cities. He would recruit these singers in them, them cities. And of course the singers would get excited because they like, oh my God, this might be an opportunity for me. They ain't make no money. They. They weren't getting nothing out of doing this stuff. And I'm like, this man is trolling.

Except for some nondescript, oversized, baggy sweatshirts that they could wear. He had them out in the desert looking like a cult. I really thought this was going to be the, the beginning of the cult of Kanye. And I really think that. I thought there was going to be a whole Branch Davidians situation where he was going to have a compound of people living with him. But for whatever reason, that fizzled out and that did not happen. But yeah, it, that to me, that's the, the manipulation. That's the manipulative part of him and the, the things that he's learned along the ways and how to, you know, I'm already being. My ego is already being fed and I can make people do things that they want to. I'm gonna go back and make y'all love. And if that means I'm gonna have to, you know, tug on you, emote tug on your emotional strings by make. Putting it into gospel music, that's exactly what he did. And, you know, God bless everybody that was into it and loved it, and they thought this was going to be the second coming. But I think you got spared. I think you got spared, your life was spared. You got spared from being incurring travel fees for going to a compound way out of nowhere. Your family was spared because they, they, you didn't get separated from them for months, even years, and got J. Ray he had a school. Imagine if school is still in function, but imagine if he had got his hands on young people.

The Donda Academy. The Donda Academy is called the. It's called the. The Donda Academy. So now this is a second thing that I just don't understand why people did it. The school closed abruptly in 2022. So it opened. It was opened in 2022. It was grand opening, grand closing. It opened in 2022, and it closed in 2022. Here's the thing. Here's the thing. I do not understand. I will never understand this. I do not understand why we keep falling for. When everybody's. When somebody's doing something bad, all of a sudden they go to Jesus. I. We see it in our personal. I've seen it so much in my personal life. I know what that is. Why in the world do people keep falling for that? I have no. No idea. Two, I do not understand why these folks with problems. We would send children to their schools to learn things. Yay. Is not an educator. In fact, he is all the things that are not education. Why would these people send your children to a school founded by him? I don't understand. I will never get it.

I'll never get it either. Which brings me to this point. We've been getting into the. The. The latest documentary by Questlove about Sly Stone and the question of black genius. Yeah, we've been talking about that ad nauseam. And that is a label that we threw at that young man at a very early age, early in his career. And I'm just wondering if. Are y'all. Are we. Are we like too free handed with the. The genius label? Like, you know. Yeah, he chopped up some samples. I mean, he really chopped up some samples. And he had, you know, he was. He's excellent. You know, the off the head freestyle game was on point. Loved all of that stuff. But was his genius, as we so called it, was that actually just him emotionally leaking on all of us?

O.

And we thought. Oh, and it sounded good. It sounded good. So we thought that was. Huh. This is good. This has a funky beat to it. And I can dance, so it's gotta be good.

I. I am not willy nilly with the term genius. Here's why I don't think Kanye is a genius. Here's why I don't think Kanye is a genius. I don't think Kanye is a genius because he's not good at finishing things. You know what makes Prince like, really like a genius. You know what makes Stevie Wonder a Genius. Because they set out to like do a thing and they finish the thing whether it is commercially well received or not. It got done. For the last three ish Kanye records, they've all been. Since that life of Pablo, people have literally said, I don't think this record is finished. And for the life of Pablo, it was evolving. Like he would update it and so the files would change, he would just change the thing. So it's not a complete project. You didn't have a singular thought that you were able to take through and, and, and yay. Has it really produced or written things for those records any years he's historically had other producers, had other writers who were helping to craft the things. That does not a genius make. Okay. You could be a visionary artist, you could be an amazing creative. Everybody is not a genius. We know why we keep calling him a genius. Cause that mofo keep calling himself a genius. And I'm looking at him and I'm looking at him like, I don't know no geniuses that be like, I'm a genius.

No sir. Now if you want to call a provocateur, sure, absolutely.

If you said I'm a provocateur, I'd be like, true. I agree. I believe you.

Letterman jacket with a big P on it. That's for provocateur. Absolutely. And as we wrap up this, this discussion, by in no means are we just dog piling on this young man. You know, we really would like for him to magically pull it together. I don't know, I don't want him to be another statistic. I'm not invested in him musically anymore.

Out.

Because I don't think he's invested in music. Just like J Ray alluded to. I don't think he's invested musically. He wants. Everything is self serving now. Whereas a genius has something that they need to give to the world, they.

Have to give it to the world.

It's like God driven in them that you have to put this out for the world to have and to hold. Whereas now we don't. Only thing we got are some like nondescript basic looking sneakers and some, and some what looks like prison uniforms for fashion. It's just not, it's not giving. It's not giving.

It is not giving. I think that's. It's not giving. As the kids, somebody needs to let him know. Somebody needs to say, baby, listen, I know, I know you've been running around telling the people that you a genius. It's not giving. It was cute. It was cute a decade ago. Now you're running around here with all of this other foolishness. It's not. It's not it.

Well, J. Ray, while we non geniuses over here at Q Points continue to do our show, what we do need is the listeners to continue to follow us and support us. So let them know how they can do that.

Absolutely. Yo, listen, if you can see our faces and hear our voices, we appreciate y'all so much. Go ahead and hit the subscribe button wherever you are so you get notified about new episodes of Q Points and you can do us a solid. This is absolutely free. You can share the show with your friends, family, colleagues. If you love Cue Points, chances are they will love Cue Points as well. And it helps to spread the word about the show. Visit our website@qpoints.com there you can sign up for our email newsletter. You can read our magazine Cuepoints Mag, and you can listen, listen and watch all of the old episodes of Q Points. There's a lot of them to tune into. There's a lot of content over there. And if you want to support the show, you can shop our store@storeqpoints.com you can get yourself some fresh gear and stuff. We appreciate y'all. We love y'all.

Like I always say, in this life, you have an opportunity. You can either pick up the needle or you can let the record play. I am DJ Sir Daniel.

My name is J. Ray, y'all, and.

This has been Q Points podcast Dropping the Needle on Black music history. We will see you on the next go round. Now, where the hell is my croissant?

Sa.