MC Supernatural is widely recognized as one of the greatest improvisational freestyle rappers ever to pick up a microphone. Since he came on the scene in the early 1990s, the Marion, Indiana native has won epic battles, made music with some of Hip-Hop’s elite while living on both coasts, and even entered the Guinness Book Of World Records for the longest freestyle. However, there is two specific Rap battles that heavily define his career: his 1990s showdown with Craig G, and his 1999 clash with J.U.I.C.E. Both battles are embedded below.

Supernat’ is the latest guest on The People’s Party With Talib Kweli. Notably, Kweli considers the artist born Reco Price to be one of his best friends as well as a onetime mentor. In the 1990s, both men were living in Brooklyn, New York. The had ties that included freestyling in Washington Square Park, dealings at Brooklyn’s oldest Black bookstore, Nkiru Books (which Talib and Yasiin Bey later purchased), and watching anime. Throughout the conversation, Supernatural suggests that it is one of his most definitive interviews in a career that spans nearly 30 years. He admits that he is dropping knowledge not available in other conversations. Included in the discussion is the former KISS FM radio show host (alongside DJ Enuff) claiming he pioneered the bomb sound-effect that has become a trademark to Funkmaster Flex’s competing show. Additionally, Supernat’ recalls securing his Elektra Records deal without a demo tape, but instead by freestyling for executives, including Sylvia Rhone. He also speaks candidly about newer freestyle rappers, including Harry Mack, who may not be paying proper respect to Hip-Hop culture and its forefathers.

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The chat inevitably winds to his infamous battle with Juice Crew member Craig G. Just a bit earlier, fresh off his Elektra deal, the MC earned a spot as an alternate at the NMS battle. In the end, he would defeat Richmond, Virginia’s Mad Skillz in the final round of the New Music Seminar Battle For World Supremacy, after one contestant did not show up. “That’s where the antics of Supernatural came to life. In comics, they always have this thing where they say, ‘it’s your first appearance’—like when Spiderman first appears in the comics…boom, that was my first appearance,” says Supernatural near the 38:00 mark. “And all those antics, from imitating rappers, to rhyming about things, to [props], I put on a spectacle that day. Hip-Hop, at that point, had probably never seen anything like that.”

However, things were changing. Supernat’ had leveraged his momentum—including the New Music Seminar victory—into a radio show. He had already secured a record deal, was also a standout regular on Stretch Armstrong & Bobbito’s radio show, and working extensively in the studio with KRS-One. However, he had also become a target in the competitive space. According to Talib Kweli, Stretch & Bobbito’s show callers regularly demanded a battle between Supernat’ and Craig G—a former Marley Marl protege who had a Rap career spanning the last decade. Those in the know were aware that the Queens, New Yorker had been battling in a time following his Atlantic Records tenure.

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Talib Kweli says he was in the crowd that night. Supernatural had been hosting Lyricist Lounge, a New York City club event that would later work in tandem with Rawkus Records in the ensuing years. “It was at the Sheraton ballroom; it probably held about 5,000 people, maybe,” ‘Nat recalls. Kweli remembers Lyricist Lounge co-founder Anthony Marshall using the microphone to point out that Craig G was in the building. “They put him on the spot,” Talib contends. Kweli, who says he later built a business relationship with Marshall and Lyricist Lounge co-founder Danny Castro, notes, “I feel like [the battle] was irresistible to them to create a Hip-Hop moment.” ‘Nat responds, “They had to. And I’ve always been that for a lot of people, in good ways and bad ways. All I had to do that night was go, ‘You know what? [I will do this] on my terms.'” Kweli reminds, “But what you said was, ‘Craig G, where you at?'” Supernatural agrees, “I said, ‘If he’s in here, where you at?’ By the time I was unraveling my locks, this dude was already on stage running around. He had a 40 [ounce of beer] in his hand. He was hype as hell.” Talib Kweli contends that Craig G knew he was going to battle Supernatural that night. The guest agrees, “Everybody knew, but me.” He adds, “That was always a touchy thing to talk about. But at this point, it’s part of my history, and I can never shy away from that.” He continues, “So by them doing that, all I had to do—and this is a lesson for any young artist: never let your ego control your intellect. Your intellect is the moment where you go, ‘You know what? Let me save these bars for another day, so that I present myself in the right way.’ My ego overrode my intellect right in that moment, and it was being guided by others.”

Talib Kweli says that energy swayed the outcome. “Battles like that are not about who’s the better rapper, who got the best bars, or who got the best punchlines; it’s about the energy of the crowd, and the energy of the room.” Supernatural recognizes that he was a target. “I was like the white buffalo. Everybody wanted to take a shot at me back then, if they could.” Talib agrees, and points to the ’94 battle. “Craig G came with bars about Indiana, and he came with certain bars that people in the crowd was cheering to the point where people wasn’t paying attention to the battle, it became about the energy in the room.”

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He then adds, “Diddy was in the room. He was called ‘Puff Daddy’ back then.” Supernatural covers his eyes in frustration, adding that Dame Dash was present too, on stage. “For people going back and looking at this sh*t on YouTube, you hear people starting to chant, ‘Craig G!'” According to both MCs, Diddy—who judged the ’93 NMC battle—chanted on behalf of Craig G. “He jumped on the table. Diddy had the Bad Boy [Records] campaign, with the signs. Diddy was a natural, charismatic leader.” Kweli believes Puff influenced the crowd to support Craig G, not Supernatural. The guest reflects, “And you could not hear me. I’m rhyming; you can’t hear nothing I’m saying…the first round was a great blow. The second round is where that started. And I’ll tell you something, man, ‘Hey Diddy, I still remember you standing like four rows back, and you had on a FOX [motor-cross] shirt.'” The guest thinks there was no ill will to Puff’s campaigning in the battle. “He was invested in Bad Boy [more than the battle].” Kweli believes Puff’ rode the wave of the crowd.

Supernatural expounds being defeated. “I swear to you: it was one of the hardest [losses]. It’s so dope to talk about this now, because I’m healed—but at one point, when you’re wounded, especially from something you love, it’s a lot to cope with mentally. So, I remember walking back through the audience, [hearing], ‘Yo, ‘Nat got served,’ ‘Oh my God; Nat’s dead,’ ‘His career is over,’ ‘Yo, that ni**a’s garbage.’ I got home and, ‘brrr,’ every five-f*cking minutes the phone was ringing. And that’s how ill New York was. There was no Internet; motherf*ckers got on the horn quick, ‘Yo, Nat got his head…he got massacred.’” He remembers kicking his phone across the room in his apartment. He realized at the point how fickle and highly territorial New York Hip-Hop fans were. “It was just that moment in my career where I was like, wow, they can love you one year, and hate you the next.”

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Years later, Sway & King Tech contacted Supernatural with the prospects of another battle: MC J.U.I.C.E. Like ‘Nat, the Chicago, Illinois MC was a regular on The Wake Up Show, which was known for cutting freestyles. At 61:00, he notes, “They were like, ‘We got this guy, J.U.I.C.E. Son is mad nice; we think he can beat you.'” ‘Nat agreed. “I said, ‘If this time we battle? We battle for the paper. Y’all gotta put some money up; I’m not getting into the ring for entertainment anymore—not for [your] entertainment. So they were like, ‘We got $5,000, a plane ticket to L.A., Reseda Country Club, we’ll hook it all up.’ I was like, ‘Done.’ Keep in mind: I had never seen J.U.I.C.E. rhyme not had heard him, up to that point; I’d only heard the legend or the myth of J.U.I.C.E.” Supernatural says he went to New York City’s Fat Beats Records, and bought anything that he could study.

Some days later, in front of a crowd that included Pharoahe Monch, Chali 2na, The Cali Agents, Chino XL, and others, Supernatural entered the ring wearing a hooded cape. He remembers a friend overhearing J.U.I.C.E. forecasting a victory before the battle. “The battle ensued, and you know the rest. Once again, I came out on top. A lot of times when I battled, I just wanted to be an artist, bro.”

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However, the victory was a product of the heartbreaking loss. “You know why I did that that night? Because I knew in my heart of hearts that I was there for the sacrifice. J.U.I.C.E. would’ve been a star right now if he won that battle—a superstar. Huge, ’cause you beat two of the illest ni**as of all-time, Eminem and Supernatural. That’s a hell of an accomplishment. He probably could’ve been far beyond [what he is now]. But once again, the lessons. [With] Craig G, the lesson was, do you go into this with that same mentality, or do you go, this time, prepared?” Kweli notes the difference as a student of both battles. “So, I said, you know what, I’m gonna throw my sh*t in the arena one more time. But this time, like I said, I watched him twice, I didn’t say nothing else for three weeks. I practiced. But really, what was I practicing for? I say, I live in the moment.”

Supernatural adds that he rehearsed his timing to close friend Pharoahe Monch’s “Simon Says” instrumental. It was one of the tracks he was allowed to pick, unsure of when the DJ could use it. The rehearsal worked to his favor. “I’m not gonna be the sacrificial lamb for you dudes…I’m ridin’ for mine right now. And that’s why I said, ‘Look judges, I got ’em hypnotized / This wack motherf*cka can’t even look me in my eyes.’” Because one thing my father said: ‘If a man can’t hold your eye contact for two seconds, he’s a punk. Don’t f*ck with him.’ That’s pop duke; I love you for that, Pop. And a lot of you cats out here can’t hold eye-contact—the hardest of the hard motherf*ckas can’t hold eye-contact, only because of your insecurity.”

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Both battles are included on Supernatural’s 2003 album, The Freestyle Files. At the close of the interview, Supernatural reveals that he wants to teach freestyling as a form of mental martial arts. He is currently working on an album, The Frequency, which features Talib Kweli. Supernatural, now based in Southern California, says he is a more confident producer.

Additional Reporting by Jake Paine.

#BonusBeat: Video clips of Supernatural’s battle with Craig G, followed by his battle with J.U.I.C.E.: