[NOTE: This interview — ‘Combat Jack: Above The Law’ — originally appeared in RESPECT. #25 two years ago, courtesy of Editor-in-Chief-for-life Adell Henderson. In honor of Combat Jack, we’ve brought this gem from its print origins into the digital realm for fans to enjoy. We’ve also included recently-released, poignant words from Adell in memory of this moment in time. RIP to Reggie Ossé, one of our culture’s greatest pioneers.]
There’s no denying that Reggie Ossé is hip-hop. For those who may have caught the fortysomething-year-old Brooklynite during an interview on his popular weekly podcast, The Combat Jack Show, there’s no questioning whether or not this guy is committed to moving the culture forward. During a former life as a rising entertainment attorney, Ossé was part of several multimillion-dollar deals in the ’90s and early 2000s for clients such as Jay-Z, Damon Dash and Bad Boy Entertainment’s Hitmen production team. Toward the end of that run, piracy and Internet trickery caused the music industry to lose a lot of money, and Ossé discovered he had already begun to lose his passion for practicing law. Soon after, a new literary deal added to his confidence that he could creatively write, and a war-ready pseudonym gave him the freedom to blog without judgment as he transitioned into his new career. Fast-forward to today and Ossé is happier than ever interviewing various rap music heroes, new jacks, influencers, supporters and activists through his Loud Speakers Network platform. He’s very appreciative of his journey and credits his legal background for making what he now does for a living not as hard. Pause.
RESPECT.: Back in the late ’80s, you had a bachelor’s degree from Cornell University and a law degree from Georgetown University Law Center. Why the hell did you accept an internship at Def Jam instead of going somewhere to get paid?
Reggie Ossé: Back then, the grind was different. It wasn’t about getting paid; our shit was about your craft first. At the time, Vanilla Ice and MC Hammer were selling millions, even Public Enemy was selling millions of records. But back then, it was really about the craft and making money in ’89, ’90 and ’91.
If that was the case, what was the Ivy League kid doing in college? Why law school?
The advantage of law school was that it took me right to the steps of Def Jam. During law school, I didn’t know where I wanted to go, but I always say even if you don’t know where the journey is ending, keep moving.
So at that time, law school was a safe career move. Were you interested in doing interviews back in those days? Were there any journalists on your radar?
I used to be so amazed at Bönz Malone in his prime, a young Dream Hampton, and the Mind Squad at The Source was amazing, man. The only way I can kind of convey who those cats were to me was they were like the Wu. It was a collective of intelligent writers that was covering this shit with accuracy like I’ve never seen before.
Exactly. And we’re talking early stages of hip-hop, when there were still a lot of doubters about rap music and whether it would stick around.
Back then black attorneys and black executives, most of them fought against rap, because to them it wasn’t music, it was a fad. Compared to people who played instruments, who spent years perfecting their craft to be at the top of their game in terms of black excellence in the form of music—here comes this shit. It was an insult to them, and I can understand that.
You eventually earned major stripes for being a stand-up, passionate attorney who helped make the industry believers after working with Damon Dash and Jay-Z at Roc-A-Fella in the very early stages, when every record label told them no. You began to make a name for yourself, but you still lacked confidence. Why?
I was a fine arts major, and now I’m perpetrating the fraud like an attorney in the music industry. When you’re not confident in a high-pace game, that shit is maddening. The biggest blow that made me really question this game for me was when I lost Roc-A-Fella as a client, right after everything was done for Reasonable Doubt. I didn’t like how that felt. That shit shook my confidence more, and I didn’t ever want to be in that situation again.
And ironically, they went on to sign with Def Jam. So basically, you felt that you helped build that empire from the ground up, and once they got on, they didn’t need you anymore. Did you know then that you weren’t cut out for the legal side?
That was the seed. That shit was embarrassing. If what I’m doing doesn’t afford me the full sense of security of knowing that I own the shit, I’m not going to be doing this all the time. What happened with me because of Roc-A-Fella also opened up the floodgates for our business even more. But every time an artist, producer or songwriter I worked with started to bubble, I would start feeling the wave.
Damn. They’d start to blow up and they would leave.
Even though I couldn’t put my hand on it, I feel what was starting to manifest was that I had something else to do on a deeper level. That chain of events was the sign put in motion that made me think I didn’t want to do this no more.
During your exit out of that chapter of your life, you got a book publishing deal and wrote Bling: the Hip-Hop Jewelry Book, which was a good look at the time. As you were exploring other career options, you discovered some of the early hip-hop Internet blogs.
Around 2005 that was the black hip-hop renaissance. The minds of the community I started to discover on blogs kind of reminded me of the old days of The Source in terms of how raw it was. It was so many dope hip-hop blogs, and when you found them, you treasured them.
So legend has it you got bit by the bug but felt too embarrassed to write under your real name. And that’s when the Combat Jack moniker was born?
I immersed myself in that dialogue, but I wasn’t gonna do it as Reggie Ossé. I’m old, I’m established, I didn’t want my colleagues reading about shit that I’m writing; I’m a lawyer. But I was like, “I’m gonna try this little blog shit.” And it wasn’t even a business move or a career move; I’m fucking around as I figure out what my life is gonna be, and that shit got addictive.
And as fate would have it, you were actually good at it, and people began getting addicted to what you were writing.
Not just cats I didn’t know, but cats I respected—cats that I knew or know about in the industry, but we never really met. When they started reading, then I was like, “Yo, I like this shit.” The Combat Jack name was the cushion. This was my secret alias, because cats who knew me didn’t know I was doing it, and then some of them began emailing me like, “Yo, you read this Combat Jack shit? Is that you?”
So the blog blew up, and after a while, Dallas Penn convinced you to link up to do a Combat Jack Internet radio show back in 2010.
We would tell these stories about how it felt back then, and we had this chemistry. The shit just started growing—NY Delight, Premium Pete, DJ Ben Hameen, Matt Raz—and it was barbershop talk with some smart guys, and some guys who weren’t too smart. Then we started getting guests, and that changed the game.
For a small Internet show, you guys hit a lick by getting the late, great Sean Price as your very first guest. But you were also letting a bunch of new, young talent get their first look as well.
I miss my early days of The Combat Jack Show, because it was really like, “What’s your name? Troy Ave? Come on the show. Action Bronson? What’s up?” This is their first time on any media being interviewed. And then the show started to morph and become more guest driven, but I still loved the freedom of doing whatever I wanted.
Even thought it was very amateur and grassroots, you had great momentum. Did you have any idea what you guys were creating?
The narrative at the time that I was playing in my head was that me and Dallas were filling the void that was left by Stretch and Bobbito. We came from that era, we knew them, we knew some of that humor and sensibility, but we were out there doing it now. I have so much respect for them. I’m not comparing, but they were a direct inspiration for us.
Even for those who weren’t living in New York City during that time, the Stretch and Bobbito show was recognized and celebrated as one of the illest hip-hop radio shows during their run in the ’90s. But after you guys came into your own, and the Internet radio situation ended, the floodgates opened up, major guests opened up, and you and Chris Morrow introduced the Loud Speakers Network.
RZA, Spike Lee, DMC, and while we’re doing the show, Chris was like, “This is great and all, but what’s the end game? Let’s bring new podcasts to the game.” So we had Sneaker Fiends Unite, which was another podcast that we launched with Premium Pete and Dallas Penn about sneakers; we launched Fan Bros and another show called Reality Check. And then we launched a show called The Read with Kid Fury and Crissle, and that shit was the next level. The first week they dropped, it was okay; the second week, they did our numbers; the third week, they passed us and ain’t never looked back.
So you obviously don’t feel a certain kind of way about the competitive podcast marketplace, because you’re putting other people on. Or do you truly have an “F-your-podcast” mentality?
It’s not a crabs-in-a-barrel mentality—that shit is just childish. I want everybody to thrive. We’re too grown for this, and there’s so much more that all of us can get from propping each other up. This tearing-down shit that some cats are really infusing into the game right now, I get it, but it’s bigger than us right now.
Then I’m sure it’s safe to assume there’s a lot more on the horizon for the Loud Speakers Network in the near future?
I don’t want to let the cat out the bag, because the tweets is watching, but to answer your question without getting too in depth: It’s really just about bringing a different level of quality, production wise, to the work we’re jumping into. Within the next year, we will have once again changed the rules of this game of hip-hop/urban multicultural podcasting.
#RIP to Reggie Ossé aka Combat Jack. This dude had no idea how much he transformed my life while I lived vicariously through his. His infectious voice and effortless journalism skills not only introduced me, but got me addicted to the podcast game. First as a fan, then on to an influencer and now as a producer. Two years ago I featured Reggie in RESPECT Magazine. It wasn't until later that he told me that this was the first time he had been featured in an actual physical magazine, so he was excited. Although we were on a budget and pressed for time, I insisted that we send a photographer to shoot him in his beloved borough of Brooklyn to allow my newest hip-hop hero to have his moment, and he did. From there we didn't talk much, checked in via text from time to time, only hung out in person once, but the time spent was enough to bless and inspire me for a lifetime. I actually sent dude a text this morning an hour before I received a text informing me of his passing. I constantly told him how dope he was. I'm thankful that I HEARD what he said to me before he left us. I'll continue to live intentionally and push the culture forward. May God bless his family, friends and loved ones. So long Reggie… 🙏🏾👑🎧 #DreamThoseDreams #CombatCancer #HipHop #RaiseTheBar #Brooklyn #Legendary #444 #Internets #the80way