Interview by: Martin Bauman

Remember Gemstones? Back in 2007-08, the Chicago artist (real name: Demarco Castle) was getting ready to take over the music world with his heavily-anticipated Troubles of the World album, after appearing extensively on Lupe Fiasco’s Food & Liquor and The Cool albums and catching the world’s (and Kanye West’s) attention with his single “We On”. Just as his career was about to take off, a series of events took place that would forever alter his future: the incarceration of 1st and 15th Records’ CEO, Charles “Chilly” Patton, the subsequent disbanding of the FnF crew, and the death of his close friend St. Nic all changed the course of Gemstones’ path. Many of you likely haven’t heard anything from him since. As Gemstones would tell you, he’s only just begun.

After releasing On The Road To Glory: My Story in 2010, Gemstones is getting ready to release his album Blind Elephant, preceded by a mixtape titled Elephant In The Room. The Come Up Show caught up with Gemstones to discuss his upcoming projects and what brought him to where he is today. We spoke for over an hour, and the result is a 4-part interview series in which Gemstones opens up on a wide variety of subjects, from working with Lupe, to the death of his close friend St. Nic, to his beginnings as a rapper. Check out part 1 below, as Gemstones talks about his upcoming album and mixtape, how he started rapping, meeting Will Smith, and working with Lupe Fiasco.

TCUS: Your latest project, Elephant in the Room, is about to drop. What’s the elephant in the room that you’re referring to?

Gemstones: Me. Gemstones, [as] the elephant in the room, just amongst all rappers and singers. I feel like I’m the one that sticks out. I’ve always been the one that stuck out [amongst] all rappers that I’ve ever been around, and I say that humbly. Since I’ve been rapping in the industry, every time I’ve done features with rappers, I’ve always been the sore thumb that stuck out. So this project… the album is called Blind Elephant. That’s where [Elephant in the Room] started from: the album that I’m releasing, which is Blind Elephant. And when I figured I wasn’t gonna release the album yet, I said I need to put out a preshow: something free, which is Elephant in the Room.

[With] Blind Elephant, it’s like everybody would always tell me, they see something that I don’t see in myself. And the elephant comes from, you know, an elephant is big. An elephant is huge, you can’t help but to see an elephant. If you saw an elephant walking down the street, everyone would see that elephant. It was like, everyone saw the elephant was huge but the elephant [itself]. So it’s like a blind elephant. He doesn’t see how huge he is; he doesn’t see the beauty in his destruction. He doesn’t see that these people are watching him; he doesn’t see that he’s knocking over these buildings by his weight. He doesn’t see this. So that’s what Blind Elephant came from with Gemstones… like everybody can see something in me, but me. Like a blind elephant.

So right when I was almost done with the album, I was like, “no, I’m not about to give this album way for free.” So I said, “yo, let’s release a mixtape and call it Elephant in the Room, just talking about the elephant being in the room.” So that’s what I did. Now it’s the elephant sticking out, and that’s why it’s Elephant in the Room.

TCUS: Are there any guest features that are going to be on the mixtape?

Gemstones: On the mixtape, right now… no. There’s no guest features right now. But there will be guest features on the album.

TCUS: Who’s on the album?

Gemstones: Lupe […] It’s a record that was never released that Lupe and I did, that the world never heard. And I think my album will be a good time to release this record. It’s dope. The record’s like… ahead of its time. And there’s no reason [to let] this record sit dormant, you know what I’m saying? So Lupe will be featured on it.

TCUS: I want to rewind to the beginning of your career. How did you first start rapping?

Gemstones: I began rapping when I was in third grade. In my neighbourhood, I was a young kid, and [there] was an older guy by the name of Jelani. His name was Jelani, but his rap name was K-I-G. I called him K-I. And while he used to be on the block in the neighbourhood selling his drugs – he used to be sitting on the fire hydrant on the corner selling his drugs – and in between selling his drugs, he would rap. He would just be spitting verses that he wrote. And I’m a shorty, and I’m looking at this guy like “Oh. My. God. This dude is amazing.”

“Jelani was the reason I ever picked up a pen/ Sit back, relax, as I take you back on how it all began…” – Never Give Up

So everyday, I would come outside to hear this dude – in between selling drugs – rap. And I would go in my grandmother’s house, I would find an ink pen, and I would just start writing. Then I began listening to Spice 1 and MC Eiht, and all these guys growing up, as I was like nine or ten. And I jumped in a rap group with my cousins, and we called ourselves Shorty Mobsters. And I began to like rap… I loved it, actually. And from third grade, I just stuck with it. Then the little group I was in with my cousins broke up, and I stuck with it.

“On a tape recorder rhyming for hours, we did it in/ Formed a rap group but we never came out, because we was kids.” – Never Give Up

So third grade turned to fifth grade: still rapping. Fifth grade turned to eight grade: now I’m in talent shows. Then I went from eighth grade to high school: I’m still sticking with it. Now I’m getting really, really, really good. But even back then, when I was rapping, I was always better than everybody who I was rapping with. I was always the best one, all throughout high school. I didn’t know I could sing until high school, though. I always had that hidden talent, because my mom sang, her mother sang, my sisters sing, my brothers sing… So I would just be singing around the school, not for real singing, but just, you know, singing, and they were like “oh, he sounds good!” Then I got into it, and I began singing. And I was labeled [as] a singer. And after that, I incorporated it into what I was doing, as far as rapping. After high school, I’m still at it, [and] I met Will Smith. He had a label called Overbrook Entertainment. He was in Chicago shooting a movie called Ali. You remember that movie.

TCUS: Yeah, yeah.

Gemstones: And so I hung with him the whole time he was here, because I was on the set of the movie. And I’m thinking, “yo, I need to get back there and meet Will. I need a record deal.” So I think like, it was me and my friend B. Sport, [and] I faked like I was one of the producers. When I saw the security move the rope to let the producers in, I just stood up straight and acted like I was somebody… tooted my nose in the air.

TCUS: [Laughs]

Gemstones: And I just walked to the back! And I’m like, “oh, I can’t believe that this is working! Oh my God!” I’m on my way to Will Smith’s trailer with the people that were walking in front of me. So I just became like a chameleon and camouflaged the way they were doing. I was almost at Will Smith’s trailer, [and] someone stopped me. He was like, “who are you?” And I said, “I’m with Will Smith.” He’s like “no, you’re not.” I said, “no, I am. Who are you?” He was like, “I’m with Will Smith.” I [told him], “alright man, I’mma keep it one hundred with you. I’m from Chicago, I rap, I sing, and I’m trying to get on.” He was like, “beat it, shorty. Beat it.” I’m like, “come on, man. Give me this shot. If you were in my shoes, you’d be doing the same thing.” So he [said], “alright, let me hear something.” So he pulled me to the side of Will Smith’s trailer, and he said, “spit something.” So I rapped. And then he was like, “spit something else.” I rapped again. He was like, “oh my God, impressive! Let me hear you sing.” So I sang something that I wrote. He said, “sing something else.” I did it again. He was like, “my name is Charlie Mack. I’m Will Smith’s best friend [and] manager.”

After that, they were out in Chicago for about five more days. Charlie Mack would call me, I went back there and met Will Smith, [he] heard me sing… but Will Smith didn’t handle the signing part [of the label], there were people for that. They loved me. And then [Will] brought this producer in named Omar. He said, “Omar is the one who did Big Willie Style,” which sold over ten million copies. So he was like, “Omar wants to hear you.” They flew Omar in from Philly, Omar heard me, and he told Charlie Mack [that] he felt as though I didn’t have what it took to be a star. My hopes and dreams were crushed, because I wanted to sign with them. I [was thinking] I was about to get my mother out [of] the hood. So Charlie Mack said, “don’t give up, shorty. Who do you wanna sign with? I have connections, I can get you plugged with any label.” But that really did something to me. And he told me to call him, but I never called him again. Well, I did call him once.

But then, I ran into Lupe Fiasco. At the time, he was Lupe Fiasco, but he wasn’t Lupe Fiasco who he is now. He was just a dude like me, in Chicago, trying to get on and be heard. So once we met, he was telling me he had met Jay-Z, and Dr. Dre, and he was plugged with this and that. And at the time, he’s eighteen, I’m eighteen, so we linked up [and] long story short – Stack Bundles was on the label at the time, Stack Bundles was signed to FnF – Long story short, I signed. We began working on mixtapes and albums. We were working on Lupe’s first album, Food & Liquor. They introduced me to Jay-Z, [and] I got on a song with Jay, singing the hook.

TCUS: “Pressure”.

Gemstones: Yes, sir. Everything began to take off. I began working on my project, [Lupe and I] became best friends… my name [started] getting known. Mind you, at this time, no-one knows who Lupe is, though. Then we cracked into the internet world. After the internet world, the buzz began. We did a mixtape, I think it was the Fahrenheit 1/15. We started getting feedback from it; now we [were] on the radar. We dropped Food & Liquor, [and] all the hip-hop heads loved it. I believed it was… it was cool. Then we went back in and started working on his next project. After that, we started working on my album. That’s when MTV hosted My Block: Chicago, and Sucka Free Sunday… and I did the My Block: Chicago CD that was released.

“You musta saw my lil video on MTV2/ My Block: Chicago, oh yeah, that was me too.” – Where’s The Love

So I hosted the whole CD, and then I made it to the BET Awards. I was with Bryce Wilson – this was years later after the Will Smith incident – Bryce Wilson was like, “Yo Gemstones, man, I missed you! How have you been?” He said, “I’ve got somebody I want you to meet.” We were at an Adidas party after the BET Awards. I’m like, “Alright, cool.” The guy had his back turned, [and] Bryce Wilson went up to [him] and was like “yo, I want you to meet my lil’ brother. He’s dope.” And Bryce Wilson [had been telling] me he had somebody he wanted me to meet. He was like “yo, I really want you to meet this dude,” so he was talking us up to each other.

When the dude turned around to see my face, it was the guy who told me years ago that I didn’t have what it took to be a star. And when he saw me his face dropped, like “oh my God.” He didn’t know what to say, because the dude he looked up to was big-upping me! Like “Yo, this dude is dope!” I hadn’t seen dude in years though. And he turned around, and [Lupe and I] had just finished walking down the red carpet. And dude looking was like “oh my God,” and I didn’t have to say anything, because it was written all over his face. He knew he shot me down years ago, and you know, you can’t stop the sun from shining. You can pause it a little bit with the clouds, and procrastinate on it, but you can’t stop the sun from shining. So I didn’t have to say nothin’ to him; he already knew what I was there for, who I was, and the whole nine. And then Bryce Wilson was like, “yo, have you guys met before?” And I’m like, “yeah, yeah, we met.” And I walked away.

Check back next week for part 2 as Gemstones talks about The Cool, meeting Kanye West, his friendship with St. Nic, and Chilly’s legacy.