Recap: Kid Cudi on Creative Trust, Criticism, and the Meaning of "Pursuit of Happiness"
28m 25s
This episode explores the art of collaboration through a deep conversation with Kid Cudi, co-created with Morgan Stewart. It highlights how a seemingly chaotic first session—starting with rejection of a studio and a long car ride—became a vital emotional foundation. The journey in the car fostered genuine connection, enabling Cudi to write vulnerable lyrics, like the spoken-word bridge in "Saltwater," which reflects on his late father. The episode emphasizes trust, risk-taking, and emotional openness as essential to meaningful artistic growth. Cudi’s confidence develops through repeated attempts, supported by his collaborator’s belief in him—even when he doubted his own ability to sing in challenging keys. The show also reveals how collaboration can transform not just music, but personal identity and resilience. Cudi’s long career, marked by self-doubt and early failure, fuels his relentless drive to become the "best version of himself." His work ethic and openness about mental health make his journey both inspiring and human. The episode concludes with a powerful reflection on how art transcends criticism—what matters is authenticity and effort. Whether a song is praised or not, creating with full intention means the work cannot be ignored. Ultimately, the narrative celebrates collaboration as a process of growth, trust, and shared vulnerability, showing that true artistry comes not from approval, but from authenticity and perseverance.
I'm like, "Yeah, motherfucker, two days to write something you don't like." I love it. I go to sleep and night loving that shit. Like, "Yeah, motherfucker, guess what? You go right about me." Did I make something that someone approves of or did I make something that cannot be ignored? If it's something creative that's coming out of you in earnest and you put your all into it, you fucking did it. For the first second to be "Fuck this," I hate the studio I'm leaving. But I was like, "Oh, God, this, this literal visionary writer." And now I have to just sit in a car awkwardly. What if we don't get along? -Right. -I had to trust you. -Yeah. -Because there were a lot of times where I was like, "I don't know if I can sing that. You'd be like, "I think you can." -Yeah. -You know, and I'm like, "I don't know, man." And that's pretty high. He's like, "This tried." -Yeah. -And I would try it, and I would nail it. I don't think we would have written something that vulnerable if we hadn't had the hour together in the car of not writing. I think it was all meant to be in a great lesson of, like, just fucking go with the flow. -Yeah. -Your chances of something special happening are much higher if you don't say no to whatever the journey of the collaboration might be. Hello, ladies, gentlemen. And everyone in between, this is "Unfamous." A podcast where we talk about the art of collaboration and the untold and unsung and unfamous stories of how your favorite pop culture moments get made. This is a very little special series of episodes. I am sitting here with my collaborator on this podcast, co-creator Morgan Stewart. Today we are going to recap my conversation with the one and only brilliant kid Cutie, who is lucky enough to call him my friend and also lucky enough to call him my co-writer. Morgan, what are some of your favorite things from our kid Cutie episode? So I really love how he's talking about going from, like, very, like, singular artists to collaborating on something that just pushed him into a new direction. Like, he wasn't afraid to push the boundaries and also his voice and talking about how much he learned there. But we'll start with how you kicked off your first ever session with Kid Cutie. Okay, cool. I mean, I'll never forget our first moment writing together. We walked into a studio on the west side and he walks in and you're like, I don't like this room. Fuck this room. And I was like, oh, God, okay. 'Cause all about the fun sway, you know? Like, it's kind of like the vibes. Old school studio where, like, there's this huge live room that we're not gonna write in. 'Cause I'd be crazy to sit in a little circle and hold hands, I mean, could be fabulous. But it was like just a long, narrow room and you were like, no, fuck this. Let's just go back to my house. And I was like, okay. So we just, and you don't live close. - No, it was a fucking journey. It was a fucking journey. It was like from Hollywood back to Calabassus or something like that. It was like, long. - Doing, like, rush hour times. - Literally. - Then we just, like, sat in your car for at least minimum an hour to get back. And it was worth it though. - It was worth it. 'Cause then, like, we actually got to know each other a little bit before we just started writing a song. So it was, like, an accident, like, a perfect mistake of, like, fuck this studio. This is uncomfortable. Let's just drive for an hour. - Yeah. - And then start writing. And it works out great. He's so respected and loved as a songwriter as, like, a singular, as you mentioned, a singular, sort of, visionary writer. That was nervous to meet him and write with him for the first time. And for the first second to be, fuck this, I hate this studio. I'm leaving. It was, I didn't really say it as much in front of him, but I was like, oh, God, like, this, this, literal, like, visionary writer. And now I have to just, like, sit in the car awkwardly. - Right. - Yeah. - What if we don't vibe, and we're, like, stuck in this car, and then we have to go do a session. 'Cause when you're writing and music is playing, it's a lot easier to distract each other from, like, who we actually are. - Right. - When you're sitting in the back of, like, a fucking SUV, with his assistant, and you're just, like, making small talk, I was definitely nervous. - Oh, yeah. Which we all know, he's, like, such an easy guy to get along with, but it's very fun. - Yeah, but, yeah, at the time. But I think, if that was me in that situation, I also would have gotten in the car because I would have been, like, listen, even if this session doesn't work out, at least I'd have, like, an insane story for myself. - Yeah. - Like, that would be an adventure. I mean, you easily could have been, like, fuck this. - Like, this is pre-schedule, yeah. - Yeah, I'm not dealing with this, whatever. And he also could have been, like, I hate this room so much. Like, we're just canceling. Like, I don't even care. But, like, you guys still went for it. I know that out of that first session, the first song he wrote was Saltwater. Do you think that song would have come out, in the same way that it did, had you just stayed in that original studio? - You know, I don't, I don't think we would have written something that vulnerable, if we hadn't had the hour together in the car of not writing. I don't think that he would have been willing to, 'cause if you listen to the song "Saltwater," he talks in the middle of the song. He, like, taught in the bridge is him talking mainly to his dad, who has passed away. No matter how many joints he would have smoked, I don't think he would have been free enough to, like, write this whole spoken word piece as, like, almost like a letter to his dad. - Yeah. - Your chances of something special happening are much higher if you don't say no to whatever the journey of the collaboration might be. - Yeah, and then actually leads really well into our next clip, which is about how he's known for smoking weed, his cutie hum. And then also just kind of, like, changing up the process of collaboration while somebody is trying something new and pushing the boundaries of, you know, their vocal capabilities. - Cool. - Really? (laughing) You know what I mean? Like, oh yeah. - I mean, people love it. - Yeah, people love it. - The cutie hum. - But this album in particular, like, the things that were demanded to be vocally, were just like nothing I've ever experienced before. - Right. - You know what I mean? So I needed to really hone in and kind of trust the process. I had to trust you. - Yeah. - Because there were a lot of times where I was like, I don't know if I could sing that. And you'd be like, I think you can. - Yeah. - You know, and I'd be like, I don't know, man. That's pretty high. He's like, just try it. - Yeah. - And I would try it when I would nail it. - Yeah. - And you'd be like, see how fucking told you? - Yeah. - You know? - Well, it's always, I think for me, it's in whether it's writing, whether it's getting someone on the mic, whatever it is. It's always like, I'm always just like, it's just music. So let's just try it in the higher key that you feel like might be too high. Just try it. And if it's too high, we just lower the key. It's no stress. Then most of the time, you'd sing it in the original key and we would all applaud. - Yeah. And that was a beautiful thing where I would, they would always leave. - I was just gonna say, we would get kicked out. - They always left, right? He says that kicked them out. Well, I guess I did. I didn't say I wanted to clear them. 'Cause I was nervous. I was nervous, right? 'Cause this is all new things for me. But they would leave and then they would come back and we would all listen to playback. And like, that was always the best part for me. Like watching Justin, like sit there on the couch and just be like, woo! (laughing) Like, go crazy, it's shit. And like, really loving it. And over time, like, my confidence gets stronger and stronger. Each song, my confidence, got stronger and stronger. - Yeah. - Yeah. - Simply because I had the support from you, everybody in the room that was working on the music. And it was just, it was so beautiful. I hadn't experienced anything like that in my career, man. - The last thing he said is so cool. Like, I haven't experienced anything like that in my career. I mean, he's been killing it. His first hit was what, 2007, 2008, somewhere in there. Like, he's almost at 20 years of killing it and to like, be able to push yourself after all that success, I think is so awesome for lack of a better word. Like, to still wanna try new things. And what's crazy about this too is I think it's great as if you're trying to listen to this to learn about the art of collaboration. He loved the cheering and the woos after he was done. If you did it early on, I learned quickly. Like, he felt like being cheered on too soon was fake. - Honestly, I would feel the same. - And he's like, this is not good yet. You're fucking lying to me. - Right. - And what is really amazing to see is that he wants to put in the work and know that it's at least decent before anyone comes in and listens and cheers him on. Where some singers, they wanna be cheered on the entire time. - Tell me I'm great. - Tell me I'm great. 'Cause I don't think that's right or wrong, it's just how each person goes. But I learned with Cudi really quick that like, he wants to be given space to do it on his own and then wants the feedback afterwards. And what was also really cool is that me and Jimmy just went to see his show. and. The one new song he does do, Mr. Miracle, is the most range melodically, and to see when it gets to that chorus, no need to lie, I think he hadn't even talked about it in this, you might have a clip of, it wasn't the biggest era of his career, this album that I worked on with him, but to see that like giving that sort of bigger, anthemic melody that he got to sing in the middle of this show, the whole audience was singing along, even though this era wasn't that massive, for that song that we were something about, like hearing the whole audience sing this more rangey melody for him. You could tell that even though that audience isn't thinking that way, it's more of a subconscious thing, but it was a really important part of the show to have that range be pushed for him. - Yeah, that's, yeah, that's a good point to bring up. He also in the show, we don't have a clip, but I think it was for Speeding Bullet to Heaven, he talked about how it took people a long time to catch on. Katy Perry even brought up, you know, some of like her songs "Deep in the Catalog" are now flying up, they were never even singled. - Yeah. - Like they're going viral right now. She has several, same thing with him. I think when that album of yours that you worked on with him came out, was it Maui Wally that all of a sudden was? - A song from 20 years before goes viral. Like yeah, him promoting a new album, somehow pushed people to some random song from a mixtape. - Yeah. - It wasn't even an official release. That actually perfectly leads us into the next clip, which is about what happens when a song leaves the artist and takes on a life of its own. - When the remix happened, it flipped the whole thing. - That feel it. - Yeah. - Like it became like, oh, this is a song we get fucked up to. Like he's talking, he's talking about drinking a drive and yeah, this is song you drink a drive to, you know? And I was like, you know, I was like, no, no, no. That's not what this point of the song was guys. I was meant to show you, like, this is recklessness. - Yeah. - You know, but over time, I learned to embrace, 'cause I saw that the remix was bringing people joy when I was performing at my shows. That was always a moment. - Yeah. - I mean, that song, I always have to have in my set. - Yeah. - Like I always have to pursue, always, always. - Such a good song. - Yeah, people look forward to coming to my show and having that last moment at the end of the shows where the fucking confetti comes down, the fucking balloons. - Yeah. - And everybody's singing pursuit of happiness and just raging and having a good time. And we're all fucking happy. - Yeah. So because of having this conversation with him when me and Jimmy went to the show, I was like, waiting for this moment and he ends the show with it. The whole time, I'm like, realistening for the lyrics about, like, self-destruction. The lesson is, yes, people will make something their own no matter what. But it also is the power of pop music. - Yeah. - That if you want to look at the details of the lyrics and go, oh wait, this is really fucked up. Like, this guy is not doing well. You can. But if you just want to listen to, if all you're hearing is pursuit of happiness, the pursuit of happiness with that euphoric, hard-hitting beat the whole time, then that's fine too. And to look around at this audience that deeply loves him. These fans love him. They are listening to the details of most songs. On this song, just that main lyric, like, I'm looking for the pursuit of happiness. And the euphoric nature of that track is all that they're noticing in that moment. - Yeah, and I've heard you talk about this several times that like, when you are structuring a song, like, one part is specifically for just like the broader audience and then another part is for the superfan. - Yeah. - Neither is wrong. I mean, that's like whatever it's making you feel, like, live your life. - Live your life. I mean, all the time, like as Good Luck Babe, that I was lucky enough to do with Chappell, as that was taking over the world and thinking about how many straight women are listening to this, thinking about like their fuck-ass ex-boyfriend who like just is not ready to be a grownup yet. And that I am so glad that that song means just as much to them as it means to queer people. For queer people, we know what that song means almost too well. It's almost uncomfortable. And I think that's the endless beauty of music specifically. The music fills in so many gaps for the listener in a good way. Of like, oh, no, this is what this song means to me. And to watch it, this happened for Cutie to talk about it and then watch it firsthand was unbelievable. - Hello, my little, un-famous friends. So the thing about the algorithm, low-miss algorithm is that she doesn't want to let people know about our podcast unless she thinks that people love it. So if you follow this podcast, what are the old school YouTubers say? Like, subscribe and follow. If you do that for me, then you will help the un-famous message of the beauty of the art of collaboration reach more people. So please do me just a cute little favor and follow this podcast and share it and do all those fun things. Bye. - And last thing I'll say, 'cause I know we have so many clips to go over, is that to watch them like rage with joy for pursuit of happiness, but then to also watch them like rage with like sadness, like on some, 'cause some of his lyrics are so fucking depressing. - Yeah. - Like so depressing. And like there's like, you know, a 22 year old girl behind us, like screaming every word to a song that's like on the verge of a suicide note. I'm like, this is just the power of art. And for her in this moment, she's partying to the most depressing thing I've ever heard. - That is why we get into this next clip where Scott talks about how he just does not give a fuck about criticism. - Oh yeah, I want this is a good one. - And it's work to write a story about it, you know what I'm saying? And especially you write something that they don't like. - Yeah. - Like I love that. Like yeah, asshole, you got to write something you don't like. - Listen to it again. - Yeah, yeah, yeah. - Listen to this thing you hate. - You know what I'm saying? Your boss is like, you got to write the kick-kitty review. You're like, fuck. It's gonna take me two days. I'm like, yeah, I'm gonna fuck the two days and write something you don't like. I love it. I got to sleep and I love it that shit. Like, yeah motherfucker, guess what? You go right about me. (laughing) You go right about me. - That is so inspiring. That's like deeply inspiring and that only comes with time. Oh yeah. Like I don't think I asked him in this. Then I don't think I've ever asked him off camera either. Like my guess, I would bet money that that is not how he felt at the beginning. And with time for him to be able to find that much joy in even a negative review, that is aspirational. That is unbelievable. - Yeah, because it completely reframes the idea of like, did I make something that someone approves of or did I make something that cannot be ignored? - Right. - And like, I don't think everyone should reframe that way 'cause there is just some shit that goes out. Even like, not even talk about music, but people are just putting out, I mean, look at all the polarizing content that's on the internet, just for attention, views, clicks, whatever. But like, if it's something creative that's coming out of you in earnest and you put your all into it, whether or not somebody likes it, if it's being seen, you fucking did it. - Yeah. - And you should be proud. - Yeah. - So is there a point in your career where you stopped seeing like criticism as a horrible verdict? - I've always had a more healthy view of it than most people because I was forced to very early on. I mean, I'll never forget like even like the village voice, which is, you know, it's supposed to be an ally. - It's supposed to be an ally. I would say really homophobic shit about my band. And not about the music at all, it called me Ponzi, which is like, basically, just call me a (beep) way more exciting. - Just be direct. - You're trying to sound smart. Like this old British term, like shut up. Just call me a (beep) or like, you know, early days of Twitter. Like even when we would open for Gaga, which is, you would assume is like the most open-minded audience in the world, which 98% of them are. There's still be the 2% that'd be like, get these like AIDS, T-slurs off the stage. - My god. - Crazy shit. So I think being so queer and so visibly queer, my whole career, I've been able force to compartmentalize feedback early on. In pop music specifically, what's interesting and this is a big, big, blanket statement, but for the most part, when you get rave reviews in pop music, it's normally for things that like, didn't end up being a hit. Like one of my favorite songs ever is Bad Lier that I wrote with Julia Michaels and Selena Gomez and Ian Kirkpatrick and the Talking Heads, just 'cause we sampled them. - Love them. - But it ended up not being a smash-smash hit and we got put that year like on every best song of the year list for that song, which I agree with them. But also, I think if it would have been a smash hit, if it would have gone number one at pop radio, I don't think we would have gotten that critical acclaim. I think because it was an underdog, then it was like cool to worship it. - So, last.
- The last clip we'll end on is what really drives Kid Cuddy despite all the criticism or taking chances on whether something will succeed or fail like why he does it. - Cool. I always had this phobia. I always had this fear that I would be a loser. - Hmm. - In school, I didn't apply myself. I got bad grades. I tried to play every sport there was, and I could never make the team. Like I just, as a kid, I just thought that I was gonna be a loser. And like when I went out to pursue music, the one thing in the back of my mind was like, I am not gonna be a loser. So I still, even though like, I've accomplished all these great things, and there's no way even if I stopped now, I wouldn't be a loser, right? I still have this thing in my head where I'm like, no, like, I have to keep pushing myself and to be like the illest version, I can never be. Like the super saying, dragon ball Z, gold hair, flying in the sky, version of Kid Cuddy, you know what I mean? Like that's where, I need to find that, and I won't stop till I achieve it. - Wow, it is really crazy, whatever shit happened to us when we were really young. How there is almost no way to ever shake it. It's just like trying to have a healthier relationship with it the older you get. I love that for Cuddy, he could just focus it only on music. It's probably is a lot like less stressful. I like every day job I had. I was like, I will be the highest salesperson at this shampoo store. I will be the best tennis player. I possibly can be, it's super young, that it was all of the bullying and like insane and sane levels of bullying that I experienced as a kid. All of that is still like, I must be the best at everything. And I know 100% that it's just because of, I think I was probably born with a natural drive, but that daily, hourly bullying that I experienced at public school, for sure made it where I was like, well, I will just be the best at absolutely everything I do. Even if it takes me 20 years 'cause the music business is real hard to prove you're the best. But like, after being dropped from so many record deals, I think one of the main reasons I kept trying and then found my success I was looking for as a songwriter was like, I must prove that like, to anyone who doubted me when I was young that I can do it. - Yeah, that exact thing that has driven you both, that's what you have in common, is also the thing that has just completely impeded people from ever even trying. - That's a great point because then by trying, it draws attention to yourself. - Yeah, I mean, if they're able to get into the room with you, like I know you give different types of artists chances, like no matter where they are in their careers, but like, have you seen that in artists that you've worked with and like, how do you help them reframe? - It can be, you know, a huge lesson that I had to learn is that I can be really an a really inspiring collaborator, but I can only help you with the hours that I'm with you. And so I have thought, I have failed many times when I was like, well, but I'm so inspiring and so driven that I'm gonna get this artist who has self-sabotaged 10 times that I know about, but I'm gonna be the 11th time and I'm so amazing that they aren't gonna self-sabotage this time than they fucking do. And so it's a really interesting balance of, for me, learning that I can't overcome everything and that I can fail. And so I have to give my time to people who are really gonna get themselves across the finish line. And I can make you amazing for those four hours a day that I'm with you writing those songs, but then you gotta go and handle the other hours. And that I can't do that because whenever I thought that I could, it always bit me in the ass every time. - Yeah, yeah, okay, yeah. So like collaboration, emotional intelligence, like working on yourself in that way, and then also just like work ethic, which is that is something that he brings up. Like he doesn't stop, which it sounds excessive, but he's just, when he's saying like, I'm living my dreams and you know, he's the hardest working person he knows 'cause he's never going to stop his work ethic just like yours is insane. So it's like, even though he is very open about his mental health issues, his lowest points in life, and like having those doubts in the past. Like yeah, working with somebody like that, it's like, all right, you've been through it. That's something really great to tap into to create really meaningful art that paired with that work ethic is going to go far. - The problem with when you are an artist of whatever medium is that like your hobby becomes your job. - Right, it's so hard to separate. Like your job is your passion. And so it gets really tricky of like when is it unhealthy or when is it just fabulous? And it's really hard, it's really hard to know. If I have two weeks where I'm not gonna write a song, by day eight, I like start writing a book that'll never get rid of this. Do you know what I mean? Like there's no way it's gonna stop. The episode's really joyful 'cause he's just such a sweet heart. But I learned, I learned, it's just really awesome to get to talk to someone that has been killing it for a long time and learn about their highs and their lows and how they keep going through all of that. And when I say highs and lows, I mean his personal highs and lows, but also his career highs and lows and how he just keeps going. I hope you enjoyed our recap, but you should watch the whole fucking thing. (upbeat music) Hello, hello, everyone's favorite part of every podcast where we say please, follow and subscribe to this podcast wherever you listen so you don't miss future conversations. And also, pretty please take a cute little second to rate the show. It's one of the biggest ways you can support us. See you next Wednesday.
Podcast Summary
Key Points:
The first collaboration session with Kid Cudi began with a rejected studio, leading to an unexpected hour-long drive in a car, which became crucial for building trust and emotional connection before writing.
The song "Saltwater" emerged as a deeply personal, vulnerable piece—featuring spoken-word dialogue to Cudi’s late father—only possible due to the unstructured, open environment of the car session and mutual trust.
Cudi’s willingness to push vocal boundaries and try new techniques, supported by his collaborator’s encouragement, led to greater confidence, artistic growth, and a powerful sense of artistic ownership and self-trust over time.
Summary:
This episode explores the art of collaboration through a deep conversation with Kid Cudi, co-created with Morgan Stewart. It highlights how a seemingly chaotic first session—starting with rejection of a studio and a long car ride—became a vital emotional foundation. The journey in the car fostered genuine connection, enabling Cudi to write vulnerable lyrics, like the spoken-word bridge in "Saltwater," which reflects on his late father.
The episode emphasizes trust, risk-taking, and emotional openness as essential to meaningful artistic growth. Cudi’s confidence develops through repeated attempts, supported by his collaborator’s belief in him—even when he doubted his own ability to sing in challenging keys. The show also reveals how collaboration can transform not just music, but personal identity and resilience.
" His work ethic and openness about mental health make his journey both inspiring and human. The episode concludes with a powerful reflection on how art transcends criticism—what matters is authenticity and effort. Whether a song is praised or not, creating with full intention means the work cannot be ignored.
Ultimately, the narrative celebrates collaboration as a process of growth, trust, and shared vulnerability, showing that true artistry comes not from approval, but from authenticity and perseverance.
FAQs
They disliked the studio environment and felt it was uncomfortable. The car session allowed them to relax, build rapport, and create a more authentic connection before writing, which ultimately led to a more vulnerable and meaningful result.
The relaxed, informal setting in the car helped Kid Cudi feel more at ease, enabling him to write a deeply personal spoken-word bridge about his late father. This vulnerability wouldn’t have been possible in a traditional, structured studio environment.
The collaborator encouraged Kid Cudi to try new, challenging vocal ranges, even when he doubted himself. This trust and support helped him overcome self-doubt, grow in confidence, and ultimately perform with greater range and authenticity.
While the lyrics are dark and introspective, fans often focused only on the euphoric, joyful vibe of the song. This shows how music can create emotional connections that transcend its original meaning and become a shared experience.
He believes that if you pour your heart and effort into creating something authentic, even if it’s not universally approved, it still represents a genuine expression of yourself and has value—proving you've done your work with full commitment.
Early in his career, he faced harsh criticism, including homophobic slurs. This experience taught him to separate artistic value from personal approval and to embrace the idea that creative work should be judged by its emotional truth, not external validation.
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