Call it an exaggeration if you want. But for some, Biggie’s infamous statement that, “either you slangin’ crack rocks or you got a wicked jumpshot” is all too real. Mikkey Halsted is the Hip Hop anomaly who has spent time with Common and Kanye West during their formative years, been signed to Cash Money Records during their post-Hot Boys years all as a resident of the crime-infested, politically corrupt Southside of Chicago commonly referred to as the “Wild Hundreds.”

Halsted logged minutes in the USBL—the same semi-pro league that produced NBA players such as Raja Bell, Darrell Armstrong and Spud Webb. He also managed to finish a master’s degree in education while signed to Cash Money. Instead of becoming yet another Wikipedia entry under “formerly signed rappers” after trading hoop dreams for Rap dreams with both Kanye and Cash Money, Mikkey took his hustle the independent route right around the time the recording industry as we know it imploded. Armed with a rolodex full of Hip Hop connects, and beats by No I.D. and other in-demand producers, Mikkey explains his goal of reaching the Kanye and Lil Wayne’s level.

Sibling Revelry Over Sibling Rivalry: “We were basically fans of the game. We come from a musical family, and we were Hip Hop heads. We had always been freestyling and whatnot. I won my first rap battle when I was in fifth grade. Basketball was my first love, and Hip Hop was always something that was for fun. Then my sister, [Miss Criss] met Kanye [West], and she was spittin’. He was blown away, and through working with Kanye, she got signed to Ramsey Lewis’ label Ivory Pyramid at the age of 14. Kanye was her sole producer and she got the deal as soon as she started rapping.”

Working With Kanye During The Early Days:
“Infamous Syndicate was on, then you also had an older crowd that Common and No ID were a part of. Me, GLC, Rhymefest, Really Doe, Cap One, Twone Gabz and Shawnna were repping for the younger cats. It was so many of us, and his spot was like the breeding ground for whoever was doing Hip Hop if Common and the older cats hadn’t accepted them into the circle yet. So we were like the little brother trying to get them to pay attention. We put out ‘World Record Holders,” and I was telling Kanye, ‘Man we need to get this stuff out to the world so people know all the stuff you’ve produced on.” Deric ‘D-Dot’ Angelettie got credit for a lot that early work via mentoring Kanye, but a lot of that was Kanye.”

Lessons Learned From The Cash Money Days: “I came out of it with a lot. I grew and wrote a lot, and I developed a relationship with Wayne. I also learned the independent hustle, because I was with two CEO’s everyday. My Producer Beat Battle’s are a page from their book. It’s about using your influence and power to put people on. At the same time, you take that new energy and use it for yourself too. It propels you. Cash Money signed me because they needed that new energy. They saw it was something next level and attached themselves to that energy.”

When The Student Is Also The teacher: “You can hear me influencing what they were doing with that whole style of record. From the first record I did on with Turk’s solo album, ‘Growing Up,’ I still have a lot of fans based off that verse alone. People were saying that was some of the realest stuff they had ever heard on a Cash Money track as far as the passion, struggle and pain of real life. That’s the element I brought to the table, and I see Wayne carrying that torch to this day. Once he got in tune with the pain and his emotions, he became an unstoppable force.”

Rapping With A Master’s Degree: “Through it all, I was still taking classes and everything. College came very easy to me. I continued my education even while I was signed to Cash Money, because it was something I wanted to do for myself. Nobody in my family had ever got an advanced degree. Me being a rapper was sending one message—especially when it seems like everybody thinks they can rap. Me pursuing that degree was sending a different message to myself, my mom and everyone else. If this rap stuff doesn’t work, I’ll go make $80,000 and then be in six figures shortly after that. And that’s something that the shorties need to hear. I’m not working, because you do have to go after your dream full-time. But, I’m not gonna be 35-years-old still developing a buzz and trying to get on. I can’t be that guy.”

Painting pictures with The Dark Room and The Photo Album: “I feel good about the situation that I’m in. I have deals on the table, but I’m still independent. I just want to rush and get this independent album out. Once I sign, I won’t have the freedom to put these projects out like I’m doing now. You have to get these records to the people, but at the same time I don’t want to cheat them by just throwing them out there. Ideally, The Photo Album would have 40 songs on it, but I’m not gonna give the label 40 songs. So I might as well put the first batch out independently. I think it’s gonna be a classic album and stand the test of time. Prolific and No ID are the two producers behind it helping me shape and helm this vision of The Dark Room right now.”

Politics As Usual In Chicago: “‘If you control a nations money, I care not who makes its laws,’ is a famous quote. The tangent that I went on in that verse from the ‘Got It Made Freestyle’ was just saying, ‘Fuck politics it’s all about economics.’ Politics is one thing. We have a black president, but we don’t have a black economic base. Chicago is going crazy right now. People need jobs and education and without any alternative, they’re out here jackin’, killing and doing pretty much everything else. So we’re winning political battles, but it doesn’t effect our people the way you think it would. It’s like a surface win. I just read that black people were doing better in the days before segregation than they are in 2010 as far as education, incarceration rates, poverty levels and single-parent households.”