Before September 11 2007, who did you think was going to win that battle and why?

Deji Osikoya: 50. Defintely, 50.

Why? Well, let’s just say that back in the day, I liked 50 a little bit. Just a little.

Okay, I’m lying.

50 Cent was honestly like a god to me at one point. Get Rich or Die Tryin’ is one of the first albums that I’ve ever owned (I was eight at the time), and it literally made me want to sell drugs. Back in the day, there was a Get Rich or Die Tryin’ game for mobile, loosely based on 50’s life and come-up story. In it, you could record songs, promote them, buy cars and jewellery, go to clubs and bribe the bouncer to let you in (before you became a star), pay for studio time, record diss songs and do drive-bys. It was amazing! I didn’t just like 50, he is the reason why I still today instinctively reach for my junk when I rap. The reason why I thought it was it’s cool to talk/rap with your teeth locked together, and mouth slightly open (before Through the Wire). And before I forget, he got shot NINE TIMES! 1…2…3…4…9! And survived! When will your fave…

Oluwamayowa Idowu: Kanye. I was the biggest Kanye fan then. Still am. I thought Kanye’s career until that point had been on an upward trajectory while 50’s weaknesses were becoming more glaring. Mr. West was not the commercial behemoth that 50 was but he was the critic’s darling on the path to success. It’s possible I believed that because it was what I wanted to believe but the proof lies in the pudding.

What moment do you regard as the most crucial in shaping the outcome?

Deji Osikoya: The day, hour, second and minute that Ayo Technology was recorded. It was over for my guy at that point. ‘Ayo, I’m tired of using technology/I need you right in front of me’ Bro…50 Cent was rapping about porn. Plus, Kanye had by far the hotter singles. It wasn’t really a fair fight.

Oluwamayowa Idowu: Can’t Tell Me Nothing dropping. Till he dropped Can’t Tell me Nothing, Kanye’s music tended to be of the more highbrow variation. With Can’t Tell Me Nothing, he essentially channeled what had been the chink in his armour into winning this battle. Can’t Tell Me Nothing with its Young Jeezy sample was Kanye playing for his first undeniable street anthem. It didn’t help that 50 who was the purveyor of that subgenre was floundering with his singles. Effectively, Mr. West turned up on 50’s turf with armored tanks blasting $100 dollar bills.

Did you believe 50 when he said he’d retire if Kanye outsold him?

Deji Osikoya: Absolutely. I was much younger and far more naive at the time. Truthfully, I don’t think the idea of publicity stunts had even registered back then. I definitely thought for sure that there would be bullets flying at some point. The news cycle was constantly churning bits and pieces about their showdown and I ate up everything that those guys were dishing. I remember getting hype because of the boxing-style stare-down at the 2007 VMAs. You couldn’t tell me that it – all of it – wasn’t real.

Oluwamayowa Idowu: People will say anything in the face of “battle” so No, I didn’t read much into it. And it was in line with who 50 was at the time- arrogant to a fault.

Why do you think things turned out the way they did?

Deji Osikoya: I have two answers for this. One is a ‘barbershop answer’, because it is inevitable that I will be in a barbershop getting a haircut one day, and right in the middle of my fade, an intense debate will break out in the barbershop over why Kanye outsold 50 in 2007. And the other is my real answer that I’ll deny ever saying, and denounce as ‘fake news’ in the future.

My barbershop answer (which I will give under duress because my barber will probably be a 50 cent fan, and my hairline is on its last leg): It was the system. The system was against 50 Cent. It was because he was too real. You know they can’t stand us when we’re real. Did you hear that Def Jam bought copies of Graduation just so it would outsell Curtis? I know, crazy right? (And then I’ll change the the subject) By the way, how come you guys only ever play reggae music in here?

My real answer (which as a mid-’00s 50 diehard hurts me to write) : 50’s whole ‘thing’ – his music, gimmicky beefs and general antics, and really just gangsta rap in general, – it had all started to lose its appeal. And I guess you could say that it was to be expected. He was the guy at one point, and being that guy, a time will come when there’ll be another guy who’ll replace you. It never fails. And when that guy shows up, it won’t matter how terrible his fashion sense is; or how he has to stand on his tiptoes to look you in the eye; or how much of a bullet non-absorbing nerd he is. He’ll be harder, better, faster, love porn more, and be even more talented at throwing tantrums than you are. And there’ll be nothing that you can do about it.

Oluwamayowa Idowu: I think 50’s schtick was getting boring. When you spend all your life fighting, you become a bigger target. With each battle won, more enemies are gained. And fatigue starts to set in. Your reaction time is slower and you’re just not punching as hard as you were. Essentially, 50 Cent was at his weakest and the Industry was moving away from him. There’s a conspiracy theory (as referenced by Deji and more prominently, Joe Budden) that this situation was manufactured by Universal (the parent company of their labels) to humble 50 who was becoming uncontrollable but I think at the heart of that, it captures the idea that 50 had peaked.

Also, the emotion behind Kanye’s music resonated more. You listen to a song like Big Brother and the manner in which it explored sibling rivalry- something we can all relate to. Even the singles like Can’t Tell Me Nothing, Stronger and Good Life all had uplifting themes underlying them.

What do you think is the most important takeaway/legacy from that episode and how has it shaped today’s soundscape?

Deji Osikoya: Sorry to focus so much on 50 again rather than Kanye. But I think the most important takeaway from the episode was that it spelled the end of ‘bulletproof’ 50 cent. 50’s four year run between 2003 and 2007 is still till this day untouchable in many ways. And up until his episode with Kanye, he was damn near omnipotent. Safe to say that after it, he would never reach those heights again.

As far as its effect on today’s soundscape? I don’t know if I can draw a direct link between that even and music today. I will say though that it highlighted the need for artists to be adaptable musically to remain relevant and commercially successful. 50 Cent stuck to his guns (pun intended on every level) which meant that his relevance and commercial success waned. Kanye foresaw coming trends, experimented, and positioned himself accordingly which meant that he thrived in those two areas. That’s how the game works. I guess what I’m trying to say is don’t roll your eyes so hard the next time you see a rapper from an older generation dab. Be considerate.

Oluwamayowa Idowu: I’ll focus more on Kanye here. Confidence is amazing and can trick its victims into thinking decisions made off the cuff were part of a larger strategy. That’s why it’s tricky to view the fall out on the grand scheme its currently viewed from. However, I believe it did offer the room for more depth and nuance in mainstream Hip Hop, effectively neutering Gangstar Rap  and this is reflected in the current soundscape. I also think it gave Kanye, who alongside Lil Wayne is one of the most infuential artists of our age, the validation he needed to experiment (read “Innovate”) more. Look at what followed: he had Rihanna on the Glow in the Dark tour,  messed around with Autotune and delivered stellar features on Put On, Knock You Down, Lollipop Remix, American Boy, dropped Emo Pop 808s, produced the bulk of Blueprint 3, made Taylor Swift famous and went on to drop My Beautiful Dark Twisted Fantasy and Watch the Throne. Looking back, I ask: Do you think his self assuredness on the fashion front (and the rants they’d bring) would have been possible if he didn’t know he’d made the retrospectively atrocious shutter shades a legitimate summer trend? Would Kanye’s Maradona esque run from 2007 – 2011 or 2013 (if like me, you love Yeezus) have been possible if he lost this battle ?  To answer the larger question, I think the greatest legacy of this win was that it catapulted Kanye into the conversation of modern day GOATs. In killing off one strand of Hip Hop culture, he legitimized another which was already in existence but in need of gas in its tank. Nothing was the same.