Words by Pedro Gonzalez • Edited by Tara C. Mahadevan • Designed by Cristobal Mora

Amid Chicago’s hip-hop renaissance of the early 2010s, a teenager from the city’s West Side conceived and began working on an ambitious project that would ultimately define his journey. With big musical ideas but limited resources, Tahj Malik Chandler, known as Saba, aimed to break out of his shell and burst onto the national scene as an artist.

Raised in Austin, a neighborhood on Chicago's western border, Saba grew up as an introvert with aspirations to follow in the musical footsteps of his father, R&B singer Chandlar, and his uncle, hip-hop producer Tommy Skillfinger. Music became Saba’s outlet, allowing him to find his voice and connect with a tight-knit collective of collaborators. Alongside his brother, emcee/producer Joseph Chilliams; his cousin, emcee/singer John Walt (a.k.a. dinnerwithjohn); and emcees Frsh Waters and MFnMelo, and DJ/producer/engineer Squeak, Saba formed Pivot Gang. The crew quickly became known for their presence in the city’s open mic scene, performing alongside the likes of Chance the Rapper, Mick Jenkins, and Noname.

By 2014, Chicago’s music scene had surged into the mainstream: Chief Keef, King Louie, and the drill movement had become a global cultural export, and Chance and Vic Mensa were being positioned as Kanye West’s heirs. Despite the media’s attempt to paint the two sets of artists as extreme opposites (nihilist versus conscious; chaotic versus soulful), Saba and Pivot Gang recognized that something so reductive misrepresented the Chicago they knew.

On July 15th, 2014, Saba released ComfortZone, a coming-of-age story and a love letter to the West Side. Drawing on neo-soul, lush chords, and hip-hop’s storytelling tradition, the young emcee delivered an album* that confirmed the potential he had shown with ComfortZone’s prequel, 2012’s GETCOMFORTable, his live performances, and his standout feature on Chance the Rapper’s Acid Rap track, “Everybody's Something,” in 2013. (*Editor's note: Though sometimes described as a mixtape, in the These Days canon, this is 100% an album.)

The West Side had produced rap stars before—including Lupe Fiasco, Twista, Do or Die, and Crucial Conflict—but few had invited listeners into this part of the city with as vivid detail as Saba, and none had repped it as passionately as Pivot Gang.

Across its 14 tracks, Saba chronicles life in Austin and his dreams to explore the world beyond it. “Welcome Home” talks about being hardened by the CTA’s Green Line and taking meetings at Def Jam, and “Burnout” asks listeners to picture him touring in England while depicting having to run back home because he lives “hella out West,” where the buses stop running early. Even in more sobering songs like “401K” and “Scum,” Saba addresses the disinvestment and root causes of violence in his community with a profound and defiant perspective.

While displaying wisdom beyond his teenage years, a natural youthful bliss permeates the project, echoing a more modest, simpler time for Saba—years before he had to grieve the tragic losses of John Walt, Squeak, and Tommy Skillfinger, and before the responsibilities of adulthood and success, including being the family breadwinner, weighed on him. Still honing his sound here, he proudly wears his influences on his sleeve, attempting rapid-fire, syncopated flows and soulful harmonies reminiscent of Bone Thugs-N-Harmony, and narrating immersive stories like Lupe Fiasco. While mostly succeeding, it’s endearing now to spot moments when he closes verses as if he's trying to fit one bar too many out of sheer excitement and hunger.

Complemented by songs about love, resilience, and an urgency for life, at the end of the album’s outro, “United Center,” Saba likens the production to the Hey Arnold! soundtrack, ending the project—one that is rife with emotion—on an intentionally joyful and hopeful note.

It can’t be understated how gifted of a mind Saba is as a producer, either. He not only worked on most of ComfortZone’s production but actively collaborated with others to be able to capture the sounds that were in his head—something musician and ComfortZone guest-feature Benjamin Earl Turner called a “Pharrel-ian type energy.”

Mostly recorded in a makeshift studio in his grandma’s basement, ComfortZone reflected Saba’s journey from a shy, reserved kid to an artist connecting with listeners all over the world and forging his own path through immense drive, talent, and serendipitous connections.

These encounters included meeting and befriending like-minded artists such as Ken Ross, Eryn Allen Kane, Jamila Woods, Nascent, and Cam O’bi, all who expanded his musical horizons in ComfortZone and future releases. It was also a hometown effort, with contributions from non-traditional collaborators such as Jon and Jacob Cuevas, who served as managers, video directors, publicists and A&Rs, as well as Saba’s DJ, DAM DAM, and mentors like Big Wiz, Chandlar, and Tommy Skillfinger.

When it comes to retrospectives, many gravitate towards mainstream hits or albums that seismically impacted culture upon arrival. But cult classics like ComfortZone have their own powerful legacy. The album wasn’t an instant breakout: it didn’t go viral, attract brand deals, or make Saba an overnight critical darling. Yet, a decade later, ComfortZone remains a fan favorite, and in many ways, it’s a blueprint for a sustainable career as an artist, exemplifying perseverance, integrity, and artistic investment for a timeless creation.

In celebration of the tenth anniversary of Saba’s ComfortZone, here’s a glimpse at the project's making from 17 contributors and friends.

Getting Comfortable Outside His ComfortZone

Saba: In my real life at the time—I'm probably like 16 or 17 years old—I'm recognizing that in order for me to put myself in a position to accomplish any of the things that I'm dreaming about all day, I have to overcome myself. I have to get comfortable, in a sense, with the life that I'm creating. And it's requiring me to break down an older version, or even that present version, of myself, which was mad uncomfortable.

I've always been an introvert, but even more so back then; I was really to myself. With all of the things that I want to do, I have to be a new person. Part of what made ComfortZone—why I knew it had to go through levels like GETCOMFORTable—is because it wasn't just the music. It was also a life experiment for me at the time, where I was doing my best to attempt to break down a version of myself and become a better version of myself. That's kind of where the idea really came from: breaking out of my own identity at the time.

Pivot Gang was also establishing itself. Evolving from a previous iteration known as the Rally, Joseph Chilliams, Frsh Waters, John Walt, Saba, MFnMelo, and Squeak became day-to-day lyrical sparring partners and collaborators.

Frsh Waters: My first impression [of Saba] was, “This nerdy motherfucker here." [Laughs] But he wasn't a nerd; he just looked like one. I guess he was a nerd, but in a different way. […] It was like, “This motherfucker's a scientist.”

He kept to himself. Him and his brother [Joseph Chilliams], they kept to themselves. But [Saba] was really into music and into the shit he was into, really about hip-hop and the original motherfuckers who were making shit hot like Q-Tip and J Dilla, motherfuckers that really sparked your interest.

MFnMelo: It was crazy seeing somebody that young be so great at something. I almost just tried to stop myself and say he was good, but he was really great even at that young age. I was energized by it. He made me believe that I can make it happen because he saw me in that same fashion.

Joseph Chilliams: It feels like all of our worlds were opening up in such a way, and not just musically, but life as well. Everything was expansion. The world felt so big, and we were seeing it for the first time. At the same time that we're putting music out and finally reaching audiences, we're also meeting lifelong and life-changing friends that are still our friends to this day—that are also making music. It felt like we walked into a renaissance or something.

The group performed at Young Chicago Authors and YouMedia's open mic events to promote themselves in Chicago while working towards landing coverage from local blogs like Fake Shore Drive and Ruby Hornet.

MFnMelo: Everybody was young, vibrant, eager and wet behind the ears still. It felt natural. There was an innocence to it. […] I feel like back then, we were just doing shit. People had an idea of what they wanted to be and all those kinds of things. The aspirations were there, but it felt more innocent.

Joseph Chilliams: All of our successes and our failures and our entire journeys are so intertwined with each other. [...] I remember trying to get in the door, and it's really funny, but it was a song that I produced by this fellow named Marzett called "Gangsta City." We made it to Fake Shore Drive, and it got Song of the Week or some shit, which meant the world back then. Essentially, [Andrew Barber] was trying to find the producer on Twitter, like, "Who the fuck made this beat? Where are they?" He did a little segment on me, and that kinda opened the door for us. Then Saba did a song with this fellow named Big Wiz, who was a writer for Fake Shore Drive and a long-time friend of ours, and that sort of opened the door for him.

Big Wiz: It was personal for me. Saba and Joseph, those are [Tommy Skillfinger’s] nephews. That's my best friend's nephews. Tommy dedicated so much of his life to me, so I knew when I met them I had to pay that back through his nephews. […] I remember telling [Barber], “If you ever fucked with me, ever, I need you to fuck with this.”

In 2012, music director Jacob Cuevas (a.k.a. Jay Caves) met Saba during a video shoot. Saba was there to help a friend with lighting on set but ended up freestyling at the end of the day. Jay was impressed. When he cofounded the digital media production company Heart of the City with his brother, Jonathan Cuevas, they both began working as a management and videographer team for Saba.

Jay Caves: I felt like [Saba] was the next Lupe [Fiasco] mixed with Bone Thugs-N-Harmony, which are obviously two of his biggest influences. And those are some of my favorite groups, too.

Jonathan Cuevas: Jacob came back to me and said, “Hey, I met some kid that is an incredible rapper.” [...] He expressed to me and our small team that he wanted to work with Saba and Pivot more closely. When I met him and I saw the intangibles, man, that's when I was like, “Okay, I'm in.” [Saba] and the guys were rehearsing in his basement before I got there. [...] Having that initial conversation, hearing his maturity, how he took his music, and how he saw his brand, it was a no-brainer.

Jay Caves: After we met him, he graduated [high school] early, and Jon and I were like, "We want to work with him. What should we do?" It became an informal handshake deal. Saba had the vision for GETCOMFORTable and ComfortZone—he already knew both titles—and he wanted them all to be tied together. This is all his vision. We were just helping facilitate it.

We had just started the [Heart of the City’s] studio at Fort Knox [which would also become Private Stock Studios], and Saba was now bouncing between his basement studio and our studio.

MFnMelo: We did a lot of recording at [Heart of the City’s studio] and we used to go up there on a Tuesday. We called it Pivot Tuesdays, and we'd have the whole day down there. We'd knock out a bunch of songs, and [Saba] was working on ComfortZone. At the time, I was working on Melodramatics. We were all working on a lot of different things in the same spaces, so we'd be able to hear what we were doing, and you could definitely hear it sounding like, "Oh, [Saba’s] making an album."

Gaining traction in the local scene and quickly making new friends and collaborators, Saba’s creative ambitions and output prompted him to release ComfortZone's prequel tape, GETCOMFORTable.

Frsh Waters: GETCOMFORTable happened because [Saba] was pushing the thought of ComfortZone to be something bigger. He wanted to build on it by making a sub-project. So he already had the music for GETCOMFORTable and I think he had like a song or two for ComfortZone. He had ideas of what it could be before I got locked up in 2013.

Saba: I started ComfortZone in 2011, and it had gone through a lot of different versions. Even while I was doing the GETCOMFORTable music, ComfortZone was already in my head as something I would be working on. And, I think, through doing GETCOMFORTable, I gained the resources to actually create ComfortZone sonically how I was imagining it.

Joseph Chilliams: I stayed in the basement at my grandma crib, and my brother was upstairs, but our studio was in the basement. So every day, I would wake up to a new hook, a new line that he changed, a new whatever. He would just sit there and keep hammering away at it.

Big Wiz: We talked about every aspect of this album while he was making it and he talked to me a lot about what he wanted to get from it. It was his first big project; people were starting to notice him and he wanted to make an impact. Mainly, I remember how he wanted the sound to be ‘cause he mapped it out sonically before he went into his lyrical mode.

Joseph Chilliams: He was always like, "What can it be?" Trying to dream of the craziest things. I remember there was this one song—I think it was on GETCOMFORTable—it's "Stay a While." I woke up to that. You know how songs just sound amazing when you're sleeping and about to wake up? That was the song I woke up to. And it was that song and that moment where I was like, "No, this man is really different." It was a force that was compelling him. He always wanted to do this and he was starting to see a way forward.

MFnMelo: When it was time to do ComfortZone, we were making a lot of music, and then some days he’d put something to the side and be like, "Alright, this is some shit that I'm working on.” It went from us making raps to us making hooks to him changing production and progression. He was diving in more as the album went along.

DAM DAM: Jacob used to cut my hair back in the day, and he went to school with one of my brothers. I had moved to Florida for my senior year of high school, so when I was in Florida, Jacob was showing me GETCOMFORTable before it dropped. He's like, “Yo, I'm working with this artist. Check out this project. We're about to drop. He's going to need a DJ when you get back, and we can lock you in.” [...] When I met Saba, I'm pretty sure it was in Jason’s [Valcarcel, co-founder of PVTSTCK Studios] back porch. He had a studio on his back porch at the time.

Close to ComfortZone’s completion, an incident would change the trajectory of the project. Saba accidentally broke his hard drive, which contained all of the mixtape’s files and was forced to recreate a majority of the project from scratch.

Saba: I dropped it. I was rushing downstairs because I wanted to work, and I fell down the stairs, tripped, and my hard drive went down every step. That was fucked up. And then I was like, "My future!" It was mad dramatic. [Laughs] I did everything I could, but the hard drive as a whole was kind of fried.

Jonathan Cuevas: We lost the hard drive and had to re-record everything, maybe about six to seven months prior to the actual drop. […] He had to re-record most of the project in his own basement, with the final mix and masters done at PVTSTCK and LPZ Studios.

Joseph Chilliams: He was producing most of it at the time, and it was a lot of chords, a lot of drum breaks, and a lot of harmonization. I was like, “This is interesting.” None of the beats at that time really went hard. It was really Neptune-y, but not like the hard Neptune stuff, 'cause he's playing the chords. Then he lost the hard drive, or the hard drive fucked up. Everything that he was working on at that time, he lost. When he started it again, it was way more precise. He got way more surgical every day. He was working on a different hook or a different song, and he was meeting all these new producers, and he was still producing himself, too, but getting better because of the people he was around.

Saba: There’s a legendary Noname song I lost when I lost the hard drive. There's one with Eryn [Allen Kane] that never came out that I loved, and then a bunch by myself. There's one with Melo that never came out. A lot got lost in that hard drive, and I do believe that this became the better project, but there is an alternate timeline where that Noname verse gets to come out. And that shit is so cold. I still have the song, but I just don't have any of the files to it, and it was over a Cam O'Bi beat.

Saba remained undeterred, recreating the project with new guest verses and additions to the production. In the end, the world received ComfortZone in the following form.

1. TimeZone [prod. by Ken Ross & Saba]

Saba: We had a show in, I'm assuming, 2013 at The Canopy Club [at the University of Illinois]. On our way to the school, a friend of mine, [Jameson Brenner], was playing this production trio, NAIMA, which is where Ken Ross, letmode [Cory Grindberg], and daedae [Dylan Frank] were from. Jameson is the person who introduced me to their music, and they were working with Robbie [Mueller], who was managing them, and he was a friend of mine. We ended up connecting, and they sent me some beats.

I remember coming up with “TimeZone” while leaving Robbie's studio on a train back home. I had Ken Ross' section of the beat kind of looping, and I was doing my best to write the song in my head. Then I went home and recorded it at midnight in our basement. The fan is on in the background, and my mom is in the background somewhere. It's just mad.

Ken Ross: I’d made [the “TimeZone” beat] for another artist named Jelani Day, who's based in Harlem, and he's a huge Jay-Z fan, so the drums on it were very Just Blaze—a kind of Black Album type thing—and Saba heard it and was like, “I love everything that's going on with this, but I have a different idea for the drums. Can you send me the stems?” I was like, “Whatever, I don't care, good luck coming up with something,” and he sent me—a day or two later—the entire song back with the new drums, the vocals, and the chorus idea. I remember sitting there in the studio with [letmode and daedae], and we were amazed. We were like, “This is incredible.”

Saba: When I heard their production, especially Ken Ross' at the time, their chord progressions were moving in a way that I was always looking to create for myself. Then, I guess my production credit, I was hearing everything at half-time, so I'm like, "Okay, well, let me add the drums then," because I'm hearing the drums a certain way, and I know how I want to rap to it. How they had the drums was good, but the flow that I was trying to do didn't fit that. So I'm like, "Hey, can I actually get this without the drums on it so that I can replay it how I imagined it?"

I still wanted it to have the bounce and, I guess, the excitement of some of the harder records that I was listening to at the time—this 2013 Chicago, this is around the drill [era]. It's a lot happening sonically in the city at this time. And I think for me, it was about doing my best to combine the actual sonic landscape of where I'm from with the imagined version of what's in my head. Meeting Ken Ross at that time, he was able to play some of the things that I heard without having the language yet to be able to describe that.

Ken Ross: From our end, we hadn't heard him go off as a producer, so to see that he was kinda on our level in that respect as well was really impressive. From there, I wanted to add some background vocal ideas after I heard the updates he had made, and I got my incredibly talented friend Caroline Davis to play sax in that outro.

Saba: “TimeZone” had a little more of a mumble feel, but that was based on the fact that it was mad late, my momma there, so I'm not trying to rap mad loud. I'm literally mumbling because I'm actually mumbling. It wasn't necessarily an artistic choice as much as that was the circumstance.

Jay Caves: The music video is very playful. It was the first time I tried to do a music video that wasn't directly correlating with the lyrics. He's saying real stuff about his future, our future. We both come from rough family backgrounds. It was real shit where, when we got to know each other, we’d say, "Bro, I want to be something," […] I feel like while the video is so fun and playful, those lyrics are so hard-hitting, and that's what resonates longer.

2. Burnout (feat. Eryn Allen Kane) [prod. by Justin Jackson & Saba]

Saba: I had a friend of mine, Justin Jackson, who went to YouMedia with me—South Sider, most of them were, but he came to the West Side with me one day. He recorded a few piano parts, thought nothing of it and went on in life. What's funny is, I was working with Big Wiz at the time as a producer. I was producing some of his music, and that's a beat that I played kind of by accident. I was opening shit that I had did recently, and I played that, and the second it played, I had to stop it because I'm like, "No, no, no, that's going in my pocket." [Laughs]

Eryn Allen Kane: Before I knew he did music, we had a class at Columbia [College] together. Even though I was a theater major towards the end of my college years, I was like, "Well, I have electives. I might as well take a music business class," and I met [Saba] in that class. A little while later, my manager [Robbie Mueller] said, "Yo, you got to work with this dude. His name's Saba," and I was like, "Oh, yeah! He was in one of my classes."

What was funny about that time was that [Saba] asked me to do "Burnout," and he gave me the beat. He was like, "You write, right?" I was like, "Yeah, I write," and I didn't have Wi-Fi at the place I was living in at the time. [Laughs] I was very poor. So I would go to this coffee shop, and I wrote "Burnout" in a coffee shop.

I'm a Back to the Future fan, so one of the things I said was, "Hey, universe, don't come at me with your bullshit / Your nonsense, your issues, can't handle it / Shut up, shut up … Where the keys to my Delorean at?" I sent it to him, and he said, "I love all of it, except Delorean. How the fuck did you fit Delorean in there?!" I was like, "I don't know, I'm just a fan. Also, I'm struggling. I'm making this shit at a coffee shop. This is actually how I feel right now."

Saba: I trusted her writing based off the song that I’d heard. I didn't feel like I had to write it for her. She smoked that shit, and that was my only edit, the DeLorean line. [Laughs]

Jay Caves: I had directors Elijah [Alvarado] and Tom [Vinn] help shoot the video and we were all excited. […] After shooting it, Tom and I were basically doing the treatment for it when Elijah lost his hard drive [with his footage]. So we're scrambling like, "What are we going to do to complete this music video?" We had some shots on Google Drive from a rough cut he had sent where these overhead shots are beautiful, but how can we make it come together? And we thought of this stop-motion idea that could be budget-saving but time-consuming, and Tom and I tackled it.

Eryn Allen Kane: I remember being so excited to have something that was more professional come out with my voice and my face. I felt so proud of myself and of Saba, and I think the video really was what made me feel like this could be really tight and I could be a musical artist that does music videos.

3. Butter (feat. Jamila Woods) [prod. by Saba]

Saba: I was really into the chopped-and-screwed vocal samples [at the time]. It's on a few songs on ComfortZone and, before that, on a lot of the stuff that I actually ended up not even putting out.

I came up with the idea for the chorus, and then from there, I vibed it out. I love the lyrics, don't get me wrong, but I think it's the feeling. The song made me feel good. It was just refreshing to have made something that feels like that. I was so sad when I dropped my hard drive because that shit was gone forever, and I had to eventually redo it. But it came out better the second time. The recording was way better because in the first version, I'm in my basement, and in the second version, I believe, I was in a studio.

Jamila Woods: I'd never heard the phrase “Butter” for hair, and I write about hair and think about hair a lot. I remember being like, "Oh cool. I've never heard that phrase.” Hair is a recurring motif in his writing—they just did the song about locs, [“Headrap”]—and I remember being into that, and it felt really good. I still start some of my days with [“Butter”].

Saba: I used to see Jamila every week during open mics, and this is another thing that the first version had that this one didn't. The first version didn't have [Jamila] on it. The first version is me singing in a really high falsetto: "They love you, who cares." Even to me back then, it sounded like a reference vocal, but not necessarily knowing who would sing it or if I would just attempt to sing it better.

Jamila Woods: I remember asking Saba, “Why is it called ComfortZone?” and him talking about that a little bit; him feeling more introverted and in his own space. And I remember really resonating with that. I think when you see people—or at least when I would see people—at [Young Chicago Authors] performing, you put them on a pedestal like, “Oh my God, they're so cool, and they're rappers.” [Laughs] [...] So it was a really cool moment to hear the inspiration behind the album and be like, “Yay! Introverted artists, there's more of us.”

Jay Caves: I remember us being super excited to get this record shot when we were traveling to California, being in LA, and going to Runyon Canyon. Walt was with us, Melo, my brother, DAM DAM. We were literally all these dudes from the West Side and Northwest Side. We were these guys from Chicago in California, basically [opening] doors that we didn't have access to in Chicago. Coming back and then finishing the video in Chicago was definitely a full-circle moment. That music video changed my life a lot, and that song is such a happy song.

DAM DAM: We did some shrooms together [while shooting the video for “Butter”]. It was me, Walt, Jacob, and Saba. This is Saba's first shroom trip, and at first, it was great. This man, Saba, was hugging a tree. He's like, "I feel like I'm attached to this tree. I'm one with this tree." [Laughs] It was amazing. But Saba ended up having a little bad trip because the path we’re on is cutting in between two trees, and there's a snake wrapped around the tree, but the head is sticking out of the tree, and it's in the middle of the path. So we all stopped, and Saba was like, “Yo, is this the shrooms, or is that a real snake?" I couldn't believe it either. I was like, “Let's maybe go off path and go this way, and let's go around the tree.” We keep on walking, but everybody's like, “Was that real? Was it fake? I don't know.”

This turned the whole trip [upside down]. Everyone was on the dark side type shit of the shrooms. We were walking down a path, and the tree roots are starting to look like snakes in Saba's head. He's like, “Bro, these fucking tree roots are looking like snakes. I'm fucking tripping.” And then Walt started fucking with him. He was like, “Oh shit, look, look, snakes!” [Laughs] And then that made Saba freak out. He's like, “Oh shit.” So I'm like, "Walt, stop it. Do not proceed with this. Stop." Then I'm looking at Saba, and I'm like, “Bro, stop, you're good with me. It's fine. I'll take care of you.” And as soon as I told him that, he stopped and he looked at me. He's like, “You got me?” I was like, “I got you, bro. Just follow me.” [Laughs] I've talked to him about this experience in the past, and he's like, “Bro, when you said that, you just started glowing. You were Jesus,” and that made my trip go from down to, “Alright, I'm good, this dude got me.”

4. Welcome Home [prod. by Saba]

Saba: I was playing Grand Theft Auto 5. This is the year that GTA 5 actually came out. That's how old this shit is. [Laughs] The band that I sampled for that [The Hics] had a song on there, and I went looking up their records, seeing what else they had. I really liked the song, and I don't think they had a lot of stuff out, so I started messing around, throwing it in the samplers and stuff.

When I'm producing—and sometimes it's a hard process to get to—but I think more than a good beat, I'm looking for something that makes me feel anything emotionally. Happy, sad, solemn, whatever the feeling is, if the beat can make you feel something before the words are even there, it's almost like an alley-oop. I went with what I felt, listening to that sample on loop and loop and loop.

Jamila Woods: I was impressed because I was like, "Wow, he's recording me, he's telling me the notes he wants me to sing. He made this beat, and he's rapping on it." I was really in awe that he was doing so much of the song himself.

Jonathan Cuevas: It became a real coming-of-age tale with that song [“Welcome Home”]. It wasn't just these bright singles that the first three tracks were. Those were intentional, hitting 'em back to back with those three. Then, in the sequencing, this one is supposed to bring some darkness in. At that moment, when I heard it, I knew that we had something very special in ComfortZone—the range that he was bringing in terms of sonics and what he was doing on the mic, the lyrics in there about having to run to the bus. […] It's sobering after those first three tracks.

5. 401K [prod. by Flex Lennon]

Saba: Jay Caves took me to one of his producer homie's house, who turned out to be Flex [Lennon]. I got a few beats from Flex at that time. There was a song called “Gurlfran” that came out before “401K”—that was my first one with him—and I liked that one just in terms of the energy that it brought.

Flex Lennon: "Gurlfran” was the first time I ever was like, "Okay, I might be a producer for real." I think "Gurlfran” was the one that solidified my ambitions as a producer. It was the first time I got real good feedback on something I produced.

[“401K”] is actually the same BPM as “Gurlfran.” With “Gurlfran” having a little bit of success, I thought I cracked the code, so I was like, "Oh, this is how I get Saba placements. Alright, cool.” If you play 'em next to each other, they're relatively similar beats, but I think [“401K”] was the modernized version of it at that time.

Saba: To me, “401k” is the most important song on the project because I think it's a lot of people's first time ever hearing me. […] I think that was probably my first song with 10,000 plays or something like that. It just felt like a very different response to it, where it's like, "Oh, okay, people fucking with this one."

It seemed like it connected in a way that you don't really have to have a point of reference to understand what I'm talking about. And it's always important to have songs like that. I feel like they humanize you to people on a regular person level.

Flex Lennon: Looking back, that song did change a lot for everybody. It was such deep content, and it was like he went to a darker side. He's usually on the more positive side, but to hear Saba saying the things he's saying on there, you're like, "Oh shit." […] That song, that's your bad day. You're pissed off, you're walking around, you're like, “God damnit, fuck this shit.’ I'm so happy that was my beat. That's one I'm very proud of.

Saba: That was the first song that I ever got engineered. I was doing all my own stuff at that time, and just hearing everything loud as fuck was like, “Oh shit, okay. I see the difference in this versus what I'm doing,” because it changed the song and made it feel completely different.

6. For Y’all (feat. Eryn Allen Kane & MC Tree) [prod. by Nascent, Cam O’bi, and Ben Free]

Nascent: I met Saba in 2012 at Heart of the City. They had a studio on the North Side. I met Jacob, I met his brother, I met Saba, and I went there with Cam O'bi. I was excited to meet [Saba] because I had seen the video [“Heauxs”] of him with Mick Jenkins. This is right around the time I started working with Chance [the Rapper] and Cam too, so I was transitioning to that new sound.

Jay Caves: I remember the sessions that him, Cam, and Nascent were meeting up at. At the time […] Saba had to primarily work at our studio. I think he preferred to do both at the time, too. So a lot of the sessions were at our studio at Fort Knox, Room 42, and Cam was out here fresh from [Las] Vegas and hungry, but he was established.

Cam O’bi: I was super impressed with Saba. First of all, the way that he rapped. There's this way of rapping that I'd never heard before. I thought it was just Chance the Rapper before I started to meet the rest of them. It's similar, in my opinion, to the Los Angeles or the California hip hop of the 90s: the Native Tongues, The Pharcyde, and Freestyle Fellowship. But also, now that I think about it, in the Midwest, there's such an influence of the West Coast over there—like with Crucial Conflict—and the South and Bone Thugs-N-Harmony. There's this way of rapping melodically and almost like freeform, rhythmically free. Saba was exemplifying this style that I’d never heard of but in his own way. I loved it so much.

I stayed in touch with him, and then he started to tell me about ComfortZone. I can't remember that much, but I do remember being excited to work with him on that because I saw him as an artist that I could really stretch out creatively with.

Nascent: Saba did tell me he was working on ComfortZone, and I wanted to be a part of it, so I gave Cam this beat I had. Cam added a little bit of post-production on it, but it was a beat that I had made in L.A.. At that time, I had just made it to make it, but I definitely heard him on it, so I gave it to him. Cam was very instrumental in that because he's the one that introduced me to Saba, but he also brought me into that world in Chicago: Mick, Noname, all of them. And Cam was coming off Acid Rap, too. I made that beat with this guy I used to work with; his name is Ben Free.

Cam O’bi: I connected Ben Free and Nascent years before I moved to Chicago. Ben was this guy online who was a jazz trainer, an arranger, who played trumpet. I would often have him play on stuff, and he also played keys. He played piano on [“For Y’all”] […], and I added some Rhodes [piano] to it. Besides The Neptunes, there was this other sound that I really enjoyed, a sound that I associated with Kanye West and No I.D. up to 2011 and beginning in 2004. Kind of cartoony sounding, like Late Registration’s intro, the piano that plays in the background while [DeRay Davis] is talking. I was thinking about that and trying to bring it out with those synths.

Saba: In ComfortZone, I'm experimenting with my voice a little more. I'm not being afraid of the things that inspired me—to do my best references of them. And "For Y'all," I remember I did a lot of Bone Thugs’ flows on it, and I always wanted to hear myself sound like that.

Eryn Allen Kane: I remember finding solace and comfort and hope and inspiration in the moments I could spend writing and making music with Saba. I knew where he was from as well, and for him to be this lyrically inclined, I thought he was so intelligent in the way he approached lyricism and piecing words together. He was so young, too.

Saba: “For Y'all” was probably the one that I was saddest about [when the hard drive broke] because I didn't know if I would be able to recreate that. This is around the time when Cam O'bi is an extremely hot commodity, and I felt like I had a great relationship with him, but I didn't have a lot of time with him. So I'm like, "Fuck, am I going to even be able to get ahold of him?" Because the thing was, I needed him to recreate the beat, which is a hell of an ask. Then I got to get Eryn to re-sing it. [MC] Tree wasn't on the first one, so again, it came out better the second time. It's all in due time. It worked how it's supposed to. But man, I was fucking terrified.

To me, that was one of my clearest songs at the time. I felt like I was understood. I felt like the mix was really sharp. Eryn sounded incredible. I had always been such a big fan of MC Tree and I still am, so I always wanted to work with him. His voice is just so soulful, and that was probably the most soul-leaning record that I had at that time. To me, that was what I envisioned for it. And it was this perfect marriage, especially since our voices were so different. […] But the way he carried melodies, to get that out of a rapper, that n***a damn near a 70s soul singer or some shit. But just telling his stories. I didn't know him that well at that time either, so I was really happy that he actually sent that back.

A part of it is, "Yeah, let's make a good song," but also because I'm at an age where I'm discovering myself and my own identity, a lot of these songs are different recollections of the shit that I was thinking about every day. So when I think about "Remembering them all, if I'm living large, you are all the cause," […] we know the result we're looking for at this time. We are not trying to fuck around with the music; this is the era of “Let's take it seriously because we might be able to better our situation. We might be able to actually make something happen with this.”

That's the perspective that a lot of those songs are written from—the same with even a “401K” there's a hungriness to it that doesn't take no for an answer. This is what I'm doing with my life because we said so. And "For Y'all," it's a lot of different things, but when I think of the chorus, it's almost like a thank you in advance. Like, "Hey, I know what we're doing because we said we're going to do this, but y'all are people that I owe it to."

7. Scum [prod. by Saba]

Saba: A song like that can honestly write itself. The melody of it is almost like a nursery rhyme. It's very simple but straightforward. Not saying simple to knock it in any way, but simple because the concept is simple.

Jon Cuevas: I remember him playing the keys and hearing him do that live. That was mind-blowing, bro. The actual record was similar to “Welcome Home,” where it is a dark song and it's also, again, the coming-of-age tale of a young man in Chicago. But the difference with [“Scum”] is that, this one has some brightness to it. The way the beat is, the sonics of the song, it’s talking about this stuff but it's also hopeful.

Saba: At that time in Chicago, I think the two—which, obviously, two is probably just a small view of it—but there were two viewpoints in Chicago [regarding the type of music being made and the people making it]. That’s what it seemed like how we were being represented. To me, at least. When I think of “Scum,” it's me doing my best to offer a different perspective. It's like, "No, I don't disagree with you, but here's more information." This is my best “why” that I can offer at the time. And again, so much of it is this is what you're already thinking so you put a pen to a page and you write your thoughts. And “Scum” feels like a song like that to me, where it's like this shit writes itself.

Jamila Woods: I think, especially for those backing vocals, I was more in the sonics of the songs, but I remember when that album came out; it was my favorite album. All my friends were really obsessed with it. And that was a really special moment because it felt like it wasn't only that the album was so great—but it felt like it was a part of developing the Chicago pride and Chicago music of our generation.

Frsh Waters: Funny thing is, I was locked up. I was at a point in my case where they just offered me my first offer, and I got denied bail, so I couldn't bail out. I had a lot on my mind, a lot that I wanted to say, and at that time, Saba was telling me all these new things that were going on within our world. Like, he opened up for Future [in 2014] or some big thing. I thought, “Oh my God, we're on!” I thought we were going to get on off everything we do, so that was the momentum going into “Scum.”

A lot of times, I was calling and catching them while they were at the studio, and they were trying to figure out how to hook me up to the mic, like, “‘How do we Aux Cord this?’” […] I was like, “I don't know, I'm locked up. Just put me on speaker!”

“Scum” wasn't written to any beat or anything like that, but [Saba] made it work. He was like, “I'm gonna use one of these raps that you record, and I'm gonna use it on my project.” I thought he was messing around or trying to do it, but I didn't think that it would actually land. When I heard the tape back—and I heard it while I was locked up—it blew my mind. I actually did this a month ago, and now one of the officers was walking during count in the morning and set a Bluetooth speaker on my sealed window and played the album for me.

Saba: It wasn't really a thought. It was obvious to me. It’s like, "He gotta go somewhere." We did a Pivot Gang record [2013’s JIMMY] and dedicated it to him the year prior. Obviously, his circumstances didn't allow him to be on the album in that same way. But I wanted to do my best to make sure his voice was still heard. He had—similar to how the other artists that I'm just a fan of—these unique perspectives that I feel like you can only get from them. The voice, the tone, and the texture of it felt important. It felt especially complimentary to a song like "Scum," based on what I'm talking about. Yeah, these are some of our circumstances, and it sometimes don't got nothing to do with this binary view of Chicago.

8. Westside Bound (feat. Benjamin Earl Turner) [prod. by Saba]

Benjamin Earl Turner: I’d had multiple attempts at trying to do some kind of West Side, West Coast thing. That was one of my mini-obsessions at the time in terms of the type of music I wanted to make. And I really wanted to sort of lean into the uniqueness of that relationship because I hadn't heard of it in rap yet. I hadn't really known about people going from the Bay Area, in particular, to Chicago.

Saba: “Westside Bound” might be the oldest song on here. Me and Benjamin Earl Turner dropped it when we first got our Fake Shore Drive plug; when we first started getting posted there. Sometimes, the releases weren't as thought out. It was just like, "Hey, we made some shit, and we're excited about it, let's send it to [Barber]." [Laughs] I think we released it under the name "West."

Benjamin Earl Turner: I don't really think we made an attempt to make some big record. It was like, “Let's keep making shit how we always do.” I do remember not liking my verse and thinking it was not what I wanted it to be. And I also remember taking a part of my verse and that becoming a part of the chorus. To Saba's credit, he's always been really good at actually producing. As a producer, he was functioning even then in a Pharrel-lian type energy where he could see how a song could get to its best point.

I remember at the time feeling like there was always that compulsion to greatness from being around each other. So you felt like you had to—and you wanted to—show up because your friends were going to show up. Every time I hit the basement, for me, it was the opportunity to make good on these people's belief in me.

9. Whip (areyoudown?) [prod. by Ken Ross & Saba]

Big Wiz: I got [Saba, Joseph, Walt, and Melo] all together one day, and I told 'em, "Man, any of these records that I have, if you want to use the record, if you want to use the hook or use the beat or use elements from the record, y'all can do that." And Saba was like, "Oh yeah, perfect because I have this song I want to use," And he used a little piece of one of the choruses for "Whip."

Saba: I always wanted to have a song on each of my projects that I didn't rap on, that I just focused more on melody or sang out a little more. I think because my father does R&B, it made me want to acknowledge that. It was around the time I was getting my driver's license, so it was something that I was constantly thinking about.

Ken Ross: Of the three songs we worked on, that's my favorite. The chorus that Saba came up with is pure pop candy for me. It's so catchy and creative. I created it as an Erykah Badu track. I was like, “If I could get Erykah Badu on a song, what would it sound like?” Then Saba heard it, and he added drums that were a little bit harder.

DAM DAM: That part where he’s like, “Are you down to trip?” He ended up adding that the day after we did shrooms. He's like, “Yo, I got this idea. I'm going to change the second part of ‘Whip’ to ‘Are you down to trip?’ And I go, ‘That's fucking amazing.’” [Laughs] He sent that song to Chance. While we’re on shrooms, he calls Chance: “I need you on this song right now; I’mma send it.”

Saba: I really wanted a Chance verse on this song, and my plan was with, “Are you down to trip…trip…trip?” And then, in my head, he'd just go crazy. But timing, scheduling, whatever, it wasn't in the fucking cards. [Laughs]

Jay Caves: With ComfortZone in general, Saba wanted to have space and dark colors, like purple and the dark blues. [As inspiration for the video], Lupe had his cover art for Food and Liquor, and that album was life-changing for all of us. Now we're here creating [Saba’s] album, and we all wanted to do that nod to Lupe. We would joke while we were shooting [the last scene], like, “Man, he might repost this.” Years later, he's on Bucket List Project and he's having a rapport with Saba. This was so dope because we really nailed it. When you look at this cover art, it looks like we brought his cover art to life in the video.

10. Westside Bound Pt. 2 [prod. by Boodah Shampoo]

Jay Caves: In 2013, MySpace was relaunching with a heavy focus on music. They DMed Walt on Twitter saying they liked Pivot’s music and we finessed that into a meeting in L.A.. We ended up shooting a couple of videos down there, securing Myspace to premier the Pivot ‘tape [JIMMY] and Sab did “Westside Bound Pt. 2” in a big ass studio.

Saba: I recorded that in L.A.. That's probably the only song that I can say that about on that project. That was my first time ever coming to L.A.; I worked with a producer named Buddha Shampoo, and he made that beat. And because I was out in L.A., it's always easier to write about [Chicago] when I'm not in the city because the things that stand out, the things that I pay attention to, the details are way more visible because you're in a different environment.

Jonathan Cuevas: I believe it was our first trip to L.A.. We went with all the guys, we rented a van, all white minivan, and we named it Cocaine. [Laughs] Anthony D'Annunzio was an A&R that hooked us up with the studio. We met him through Robbie Mueller. D'Annunzio loved the music and told us to show up to the studio. I believe that was all of our first time in a legit big L.A studio.

It was a good atmosphere. The guys were all happy we were in L.A; they were smoking, Walt and [DAM DAM] were playing around with the video camera, and everyone was having a blast.

11. Marbles [prod. by Joseph Chilliams & Saba]

Saba: That might be one of the craziest songs I've ever made, to be honest. I don't really think about it a lot because getting something like that off […] It's off me now; I don't have to think about it as much. The beat made me think of marbles, and I used to love marbles, based on the story that I told in this song [about] my stepfather. I remember writing that in my bedroom, and it felt like it wrote itself. This was my creative writing exercise. I felt stimulated by creative writing in English class and writing short stories. That was one of the few times where I actually enjoyed what I was learning and doing in school.

Joseph Chilliams: I'm always trying to find something that feels new or that I haven't heard or things that tickle my fancy. And the second I heard that sample, I was like, “Oh, that's disgusting, that's delicious.” I looped it and we buffed up the bass. There's some beats you make sure you're like, "Oh man, I got to write the craziest verse ever." But I made that, and I was making it just to make it, and I was playing beats with my brother, and he was like, “No, what is that? What the hell is that?" And he made the beat amazing with what he did to it.

Saba: It was cool to imagine “Marbles” as a metaphor for all of this other stuff while also using the vehicle of these real-life, concrete events […] through the relationship with my stepdad and how we even began to get cool. It is interesting because, as an artist, sometimes I don't think about what I'm sharing, and then it's 10 years later, and it's like, “Holy shit, I've shared that with the world.” It's mad vulnerable sometimes in ways that I never intended to be, but that's how I expressed it. That's what I had to express. So now it's like, I don't know, it's cool sharing these stories and recognizing that when you share your story, there's still room for interpretation. People get their own story from [what] I shared.

Joseph Chilliams: You know how your sibling can tell a story, and it's their story, but it's also your story, and just like, "Bro, you telling my story. Calm down." It'd be really funny getting his perspective of the things that I was totally aware and conscious of. I also make music, I'm like, “Do I want to tell the story one day? How would I do that?” So it'd be really funny hearing my life. Seeing the picture, I'm in this picture, you know what I'm saying?

Saba: Certain parts of it make me uncomfortable to hear because the older I get, the more private I feel like I've also gotten. But this is a record that I've always loved. Even talking about it, I'm like, “Damn, you know what? That's probably one of my best.” Conceptually, I never did no shit like that. That was a one-of-one.

Joseph Chilliams: The 70s was my favorite genre to mess around with at the time. Mainly because all the B sides and random songs you never heard, they got the same attention as the A [sides]. If you can find something that works, it's really, really interesting what it ends up sounding like.

Saba: [Joseph] stays with a crazy beat that sounds like some shit that I just haven't heard. I mean, he happens to be my brother, but that's the cherry on top. I'm a fan of his production. His choices are always interesting, and a lot of his beats don't really sound like other people's beats to me.

12. Comfort Food (feat. LEGIT) [prod. by Saba and Anthony Pavel]

LEGIT: I first met Saba, funny as hell, in Texas at South by Southwest. That was the first time I actually met him. I knew who he was, I’d heard of him but I wasn't super familiar. I had gotten pretty cool with his manager at the time. The homie Jon Cuevas was managing him, and they were doing a show at the Bat Bar on Sixth Street, and we were both performing on the same bill. Basically, [Saba] got added last minute, and he ended up sitting in the venue while I was performing.

I'm pretty sure I recorded [“ComfortFood”] with him at the studio. It wasn't PVTSTCK yet, though, but they had a room in there already. Anthony Pavel played the keys on that song, and I think Saba did the drums.

I think I always had [the song] with his verse. On some competitive rap shit, it kind of puts you at a slight advantage when you can already hear where they're coming from. I was like, "Okay. I just have to rap at least this good." That was my whole thought process. To this day, I've never told Saba this, but I kind of fuck with this verse a little bit more than mine because I feel like his verse sounded a little more effortless than mine.

13. Tell You [prod. by Cam O’bi]

Saba: Being able to work with Cam—who's probably one of my favorite producers in the world—meant a lot to me because I was able to see someone do his best to make time to work with me. He was in the middle of a lot of stuff, so any time I was able to link with him, I was always really appreciative.

Cam O’bi: That’s a beat I had in my stash, so I didn't make that on the spot. That one I made in 2011 when I was still living in Vegas, and I remember the Good Friday-era Kanye. “Tell You” was inspired by My Beautiful Dark Twisted Fantasy and all those Good Friday songs. And it's funny because, when I listen to it, I don't even know why I played what I played on it. The piano, to me, sounds so not a hip-hop song. It sounds like a damn near drug commercial to me. Like a prescription drug commercial. But then the drums come in, and I remember I did that on purpose. I wanted to take something that sounded like general pop and then see if I could make it hip-hop. I was actually surprised that Saba liked this beat as much as he did and made a song out of it.

Saba: It felt like an example of me challenging myself and really making something I had never made up until that point. I don't think I had many songs that sound like that. To me, there's a level of exploration to making music. It's like, “Damn, I just impressed myself because I didn't know I could make that.” And that sounds beautiful to me. Cam is a producer who consistently provided that feeling where I'm listening to something back, and I'm like, “I can't believe this is mine.”

It's very nostalgic sounding, which, to me, is the main reason I used to love Bone Thugs-N-Harmony so much as a kid, which is what got me into music in the first place. The fact that Cam is able to provide that feeling in a completely different way is one of the reasons why he's one of my favorite producers.

14. United Center (feat. Chandlar & Ken Ross) [produced by Ken Ross, daedaepivot & letmode]

Saba: That song is very much my experience on the West Side. We had the backyard where everybody would come and play ball, and it was a certain age you hit, and then you see less people coming to play ball and more friends of yours getting into shit. Writing that is when I was coming to terms with that in my own life and processing that.

Chandlar: There were definitely some circumstances in [Saba’s] life that were challenging as far as financial standing at certain periods of life, so poetically we hear some of these stories being explained through Saba's genius creativity. It's awesome to see his vulnerability and his willingness to just be honest and create from a perspective of himself. I feel like the most unique thing about what Saba does is he's vulnerable and willing to share his exact emotional state with his audience and that's a really amazing thing to do creatively.

Ken Ross: This was the one song that wasn't as fluid of a process—one email one way, another email back then the song is done, let's get it mastered kind-of-thing. I had connected with [letmode and daedae] […] [Saba] had this idea of closing out the project with the song called “United Center” that was an anthem, a collaborative anthem, and then we came up with the little piano line.

Daedae: I do remember that “United Center” was similar to a lot of songs on Care for Me in the way that we were redoing stuff a lot. We were changing stuff a lot. The song took a while for us to get to where it is. And, I mean, it's a very intricate song. It's a very long thing. That's me playing drums. I think we chopped it up a little, but it's me playing drums, Ken playing a lot of instruments, and Corey playing a lot of instruments.

Ken Ross: I think it was very heavily Acid Rap-inspired. Not that we were trying to rip off that sound, but we were inspired by the beats and the sound that we heard on Acid Rap and wanted to keep that lineage going. I wrote some crazy outro, some jazz-inspired outro.

Saba: It wasn't the outro at first. There's a different version of “United Center” that I produced. I got my dad to do some vocals on it, and I got Nico Segal to do some trumpet. And when I met NAIMA, I ended up getting them to redo it. It's a completely different vibe. And by then, it's like “United Center” is going to be the outro.

Chandlar: When he sent it to me, I don't think it was in his final state yet, but he mentioned that he would like me to put some vocals on the track, and there were some lines on the track with some trumpets. I felt like that was the way to go with it. And, of course, if Saba wants me to do something on the creative side, making music, it's an honor—it's a full circle speechless moment where I'm just really happy and excited.

Jonathan Cuevas: I remember it being the last song we recorded. I remember sleeping through the end of it and waking up a few minutes after they recorded the finished product. [Laughs] But I remember it was a celebration at the end. The joy in [Saba’s] voice, that was real. He was super fucking happy. We were done. No matter what, we were done today. This is the deadline. It's over. We did it. It'll be out in six hours.

When we were listening to it, we saw and heard stadiums, and with everything Saba's doing, I think he's still seeing and hearing stadiums. This is just the beginning, but it's written in Chicago history now and really the history of hip-hop music.

Saba's ComfortZone: An Oral History on its 10th Anniversary