"I'm a Chicagoan till Chicago ends/Till we blow like Chicago wind." —Kanye West

GLC: “There was this guy from my neighborhood who became best friends with Kanye. One day my friend came to the block and he had this funny looking haircut. Niggas was laughing at him like, ‘Man, who the fuck cut your hair?’ And, he was like, ‘My man Kanye.’ Cutting hair, when you living in the hood, that’s a great way to make extra money. He was like, ‘Man, he make beats too and he raw with that shit.’ We was trying to rap back then so he influenced me to come over to Kanye’s crib and meet him.

“Kanye’s crib back then looked at lot like my brother's crib; it was a lot of African artist type shit because that’s what his mom was into. So I felt very comfortable. And Kanye had a lot of pornos, sex magazines, and nice clothes—he was really into girls, music, and black liberation as a shorty. We connected on all of that because it was instilled in him through his mom and it was instilled in me through my brother. We both had a crazy love for the hoes.

Kanye’s crib back had a lot of African artist stuff because that’s what his mom was into. Kanye had a lot of pornos, sex magazines, and nice clothes—he was really into girls, music, and black liberation as a shorty. —GLC

“We looked at rappers like these dudes are entrepreneurs, they not working a 9-5, they not punching nobody clock. It seems like they balling in abundance and they got all the hoes. So, it was like, ‘Hey, this seem like the thing to do.’ We started making songs that weekend. This was like in ‘93. We were both about 16.

“It’s hilarious when I hear people say ‘Kanye is in the illuminati.’ No, Kanye applied himself. When we would be out chasing hoes, there was times Kanye would be with us, but a majority of the time he’d be in his bedroom making beats with the same clothes on for days, no haircut or nothing. That dude was focused since he was a shorty because he knew what he wanted to do and he had a mother who supported the shit out of him.”

No ID: “It was an interesting process with Kanye because there was so much opposition for his shit. Me and an A&R from Relativity Records, Peter Kang, actually co-managed Kanye as an artist before Roc-A-Fella and all that. After a certain amount of meetings—there’s a ton of stories in that—I said, ‘It’s not my thing, I don’t wanna get in your way. Let me just help you.’ I saw a lot of things within his personality that I didn’t think I could manage. It’s one thing to get opportunities for an artist to make it. But to manage him through a career, I was like, ‘Eh, I’ll just keep doing my beats.’

I’d seen Hoop Dreams and I said, ‘I’m gonna do a Hoop Dreams on Kanye West.’ People used to be like, ‘Why are you following him?’ I’m like, ‘Dude, you’ll see. He’s going to win Grammys.’ —Coodie

“But there were a lot of stages of Kanye. There were stages where he was developing as a producer, the stage where he had his group Go Getters, then there was the solo Kanye West. He had a little bit of a tougher edge on his records back then. He was a little gangster. All of that kinda made him grow and develop and create the right image, direction, so on and so forth. So there were a lot of different directions.”

Common: “I met Kanye through No I.D. His beats were good, but they weren’t knocking me over. He didn’t have the polish that No I.D. had because No I.D. had more experience. When he was playing beats, it was like, ‘That’s cool as a sample, but those drums...’

"But I always knew Ye could rhyme. We had a battle on this radio station once. I was drunk, I don’t think he was drunk, but some people said he got the best from me. Me being from Chicago, I was one of the first artists out, so I was like the boxing champ. We always had respect and love for one another but I never said, ‘Man, Ye. I’m going to use his beat.’

Common and Kanye West's infamous "drunk" freestyle

Deray Davis: “[Back in the ‘90s] I was working with Erick Sermon. I was going to be on the Def Squad label because I rap too. John Monopoly called me. Kanye didn’t have his deal yet and John was like, ‘I want you to talk to him.” Kanye got on the phone, like, ‘Nobody rap like me, nobody doing what I’m doing.’ He rapped to me on the phone for 30 minutes straight. The dude did not stop spitting. He probably did a whole album back to back to back. I’m literally like, ‘Yo, this kid is crazy.’”

J. Ivy: “You’d hear about him in Chicago. We knew who he was gonna be, we knew that he represented greatness.”

Coodie: “I had a public access hip-hop show in Chicago called Channel Zero. Guys like Wu-Tang would come to Chicago, I’d film them, interview them, and we would put it out and Chicago would go crazy. Kanye wanted to be on the show just like anyone else in Chicago, so he started coming around as a young kid. I’d seen Hoop Dreams and I said, ‘I’m gonna do a Hoop Dreams on Kanye West.’ People used to be like, ‘Why are you following him?’ I’m like, ‘Dude, you’ll see. He’s going to win Grammys.’”