When you hear classic Hip Hop on your local or satellite Hip Hop or R&B station, there’s a high chance that Reggie Osse (aka Combat Jack) probably had a hand in brokering the deals for those songs. Since beginning his career in the music industry over twenty-five years ago, he has literally been down-by-law as an attorney. Reggie’s supreme clientele in Hip Hop and R&B include past clients and dealings for Jay-Z, Capone-N-Noreaga, Busta Rhymes, LL Cool J, Usher, Diddy and his Bad Boy Record’s Hitmen production team, and a long list of others.

After exiting the rap game around Y2K, Osse returned in the late aughts after he reinvented himself as Combat Jack, the journalist. In 2006 he co-authored a photographic timeline of Hip Hop’s “ice” trend called Bling: The Hip Hop Jewelry Book, became a respected blogger, and a former editor of The Source magazine. He also gained a veritable following as Hip Hop’s answer to Inside The Actor’s Studio host James Lipton, addressing “the internets” via his top-rated weekly podcast The Combat Jack Show. The show also features his squadron, consisting of Premium Pete, Dallas Penn, and Just Blaze, probing their guests to speak about their careers and offer some of the greatest Hip Hop back-stories ever told.

Combat Jack’s Return To Hip Hop As A Journalist and “The Combat Jack Show”

DX: What inspired you to return to the music business by becoming a writer and coming out with the book Bling?

Combat Jack: The name came from when I started blogging because I discovered that online when I got a book deal to write Bling. When I saw that bloggers on BryonCrawford.com were candid, I didn’t want to be disrespectful because I respected the industry and my colleagues. I thought I was too cool for that, and knew what I wanted to write. I knew there was something out there for me than just being an attorney. And I had a voice too. It was like “Why is this attorney now blogging about the music industry?” I wasn’t concerned about cat’s insecurities.

DX: How did you come up with the name Combat Jack?

Combat Jack: I discovered Combat Jack from the book Generation Kill, about the war in Iraq. I just liked that name to write under the name “Combat Jack.” And I registered that name eleven years ago.

DX: You’ve had so many interviews. Who was your favorite and why?

Combat Jack: It’s hard to say, but one of my top favorites of all time I’d say my favorite was DJ D-Nice because that’s such a great story, and I was such a huge fan of BDP. The whole Scott La Rock passing; just really being able to get him just to get him to talk about it out in public. Another episode that I really don’t talk about a lot was with Memphis Bleek. That’s one of my favorites. Just really to hear Bleek’s story, and how he’s such a good sport: everybody thinking that he’s just Jay’s weed carrier, and you hear his experience and story, and I ended up having a lot of respect for him. But it’s all a blur. That’s like asking “What’s your favorite day at work?”

DX: Now that The Combat Jack Show podcast is number one, how hard had it been to stay on top since there are so many other podcasts and competitors?

Combat Jack: It wasn’t our goal to be number one. It was just us wanting to do something that we really knew we were really passionate about. There are times when cats talk shit, but I get how they are competitive. But what I had to learn was the more competitive that I get, the less I’m on my game. But the more I focus on what I do; I’ll be number one. And I’m not taking anything from anyone else, but everyone is doing what they’re supposed to be doing. I am doing absolutely what I’m supposed to be doing, and no one else can do what I’m supposed to do. If I’m looking in your lane, I’m going to mess it up. And if you’re looking in my lane, I’m going to eat your fucking food. You understand? The only thing that I’m being competitive about this is being the best Combat Jack that I can be.

Combat Jack Recalls His Genesis and 80s New York Culture

DX: Why did you enter the music business?

Combat Jack: Just the music. I came up in an era of soul, disco, and rock music. But once I heard rap, I was like, “Yo, this is my shit. I gotta get involved with this any way possible.” When I was in Cornell’s Fine Arts school, I looked around one day in that first semester and it was me and all these other rich, white trust fund-kids. I felt like I wasn’t learning anything in terms what was gonna make me valuable when I got back to New York City once I graduated. So on a whim, I decided to switch to pre-law, still aimless but got into Georgetown Law. And it wasn’t until I was in law school that I said, “You know what? Let me take these skills and apply it to the music industry.”

DX: You entered the rap industry as an intern in 1989 in the business legal affairs department at Def Jam. Was it hard or easier since you were Ivy League educated and had a Georgetown law degree to break into the music business?

Combat Jack: It was really difficult. Like I mentioned about my cousin who inspired me to go to law school and was the general manager of the fledgling Uptown Records, one of his colleagues was a brand new attorney named Andy Kavel, who had just gotten the gig at Def Jam and he needed some help. I had my hand in some of that help for over a year, and he said, “You know what? Go take this gig at Def Jam” But it was real difficult. You had to know somebody.

DX: When you attended Georgetown Law School in the late eighties, there was a lot of exciting and scary aspects of life in Washington D.C. popping off then. Do you have any significant good and/or bad memories being in the midst of all that?

Combat Jack: My only memory was that as I got older and grew through college, I kinda stopped hanging less on the block and more discovering New York City: Greenwich Village, which was poppin’, The Paradise Garage, and the underground club scene. As I branched out, New York was thriving. I was hanging out with cats like (legendary street artist) Keith Haring. You know what I’m saying? So when I would go to D.C., I was homesick because D.C. couldn’t satiate the culture palace that I was being fed in New York. No shots to D.C., but I tried my best to get into go-go, but that shit wasn’t Hip Hop. The club scene nor the house scene wasn’t what it was like it was in New York. So I was very homesick.

Combat Jack Talks Leaving Music After Biggie’s Death

DX: In that famous picture at Biggie’s funeral in Brooklyn, and you were right behind Mary J. Blige embracing a distraught Lil’ Kim. Can you describe the feeling of that moment, having front row seats to seeing Biggie’s hearse pass you by?

Combat Jack: Man, it was just despair. If anything to describe that, just utter despair. We had beefs beforehand in Hip Hop, and I remember the worst thing that happened was Wrecks-N-Effect was beefing with A Tribe Called Quest, and Q-Tip sustained some severe damage to his eye. Other than that, nobody died until ‘Pac and Big, at least onto my knowledge. Big was like a champion of the East Coast, in New York, and particularly Brooklyn. And when he died unexpectedly, we were foolish enough to think that after the passing of ‘Pac, there would be no more turmoil.

Even in that “Death Row versus Bad Boy,” “East Coast/West Coast” shit, that just got out of hand. And we were like awestruck. We were like; “We got into this industry to make money, not to look over our shoulders looking for when beef is coming.” So when Big died, it was just utter despair. I remember seeing Busta Rhymes, and him saying “Yo, I don’t even know if I can do this shit anymore.” And Puff specifically calling our office because we had a lot of deals on the table for Bad Boy, and he was like “Pardon me, if it’s not business as usual, I don’t even know if I can do this shit right now.” It was a sense of hopelessness. Not only are you talking about the emotional human aspects but its like here we are with the very best emcee on the planet, and he hasn’t even reached his peak yet, and he’s gone? Creatively, now we have to search for another one?

DX: Was it that incident or what else turned you off from being in the music business after twelve years in the field?

Combat Jack: My mantra was always that when going after a career that if you don’t love it and you’re not having fun, then do something else. And that shit took the fun out of everything. But the last straw from me was at the turn of the century, the iPod. The last straws were MP3’s, and the Towers 9/11 was another thing, man. The tone in New York got a little darker, and the music was so much darker. You’re talking about 50 Cent, Dipset, and it was just dense, thick, and dark. And I could deal with the dark shit, but I’m still accustomed to a wide array of music. And I was getting older, my wife and I had just had our third so, and I wasn’t fulfilled anymore.

We as executives, we came in the game as kids, as peers. And some were getting more money, and some that I knew from back in the day I didn’t even know who they were now. Things got a little too serious and too corporatized, too Machiavellian. And I just decided that I needed to be in control of my destiny. I was just catering to everybody else’s dream as an attorney. I knew there was something out there for me than just being an attorney. And I had a voice too. I remember being in creative sessions with clients, and they’d be like “Shut the fuck up. You’re just the attorney.”

DX: It’s interesting because in the rock music industry, lawyers may bounce ideas around with their clients. But with you as a black lawyer in the Hip Hop industry, it seemed like it was a struggle as if you don’t have the same academic credentials as Clive Davis, but you actually do.

Combat Jack: Well, the white man’s ice is always colder. That’s the problem in our community. The shift when that lawyer becomes his manager, and then his business partner that handles his merchandising and publishing. And if we did that in Hip Hop, my team would have sued. Cats get too greedy sometimes. You don’t hear about cats going at Tommy Mottola, or Donny Iner, or Jimmy Iovine, but they always go at Puff. You know what I mean?

DX: What your least favorite legal affair to deal with?

Combat Jack: My least favorite I’d have to say, and it’s not personal, was the whole Roc-A-Fella thing. Being there at the groundfloor, dealing with Dame. Dame is Dame. Dame is a force of nature. And you gotta be very grounded, either willing to take a lot, or outsmart Dame dealing with him on a daily basis. Dealing with an artist like Jay, who I said before had no leverage, and doing a distribution deal for him, and then Reasonable Doubt goes gold, Dame was surprised that the deal shouldn’t have been what was in his head. And I’m trying to explain to him that, “Yo, you gotta understand that Jay didn’t have any leverage.” And then losing Jay as a client, after all those years of really working with Dame and Roc-A-Fella, that shit hurt. You know what I mean? We lost Big collectively, and the next cat that I have who is about to pop is Jay, and I lost him as a client, oh my God, that was painful, B.

DX: So Dame fired you?

Combat Jack: Me and Dame parted ways, yeah, right after Reasonable Doubt, going into the deal with Def Jam.

DX: Reasonable Doubt was originally released on Freeze Records, right?

Combat Jack: Yes, Freeze Records. I did that deal. Will Socolove was the owner of Sleeping Bag Records back in the eighties, and then Freeze became his new label. He had his way of doing business, and who was really the only one willing to take a chance with Jay at that time. And he totally won! They were distributed by Priority. From whatever they had, they had to pass that deal onto Roc-A-Fella. You don’t get what more than the parent company is giving you, or what they have, and so that’s the beginning of the end between me and Roc-A-Fella. But now that Jay is a household name, or how Jay does new deals, dudes are like “Yo that’s your client!” and I’m like “Nope. And a lot of you weren’t fucking with him when he was my client.” (Laughs)

DX: Obviously, you’ve settled your differences with Dame since then. You had him as a guest on your Combat Jack Show.

Combat Jack: Of course. I’ve grown out of this, and I’ve grown to what I am right now because I wanted to be the captain of my own ship. I didn’t want to be defined by just any client once they blew up. That became my biggest fear: working with clients day-in and day-out, dealing with them on their projects, bailing them out of jail, baby mama drama, but you’re in their corner, right? Two or three years later, Flex is throwing bombs because he’s playing their record. And then he’s doing more shows, and you wake up from a nightmare because you don’t know if he’s gonna be your client now that a line of attorneys are after them. It’s crazy. To live that life 24/7, late at night with them during their studio time, I’d have to hover over every client to make sure that no other attorneys would come after them. And that’s not my life.

Combat Jack Details Brokering Deals During The Golden Era

DX: What was your first contract negotiation for an artist?

Combat Jack: For a rap artist, it was Two Kings In A Cipher. Deric “D-Dot” Angelettie and Ron Lawrence who helmed Bad Boy’s (production team) Hitmen. That was the first deal I ever did.

DX: “The Madd Rapper.” Deric Angelettie attended Howard University at the time that you were at Georgetown, too, with other future Bad Boys executives Harve Pierre and Puff Daddy, right?

Combat Jack: Yeah. It’s funny because D-Dot was the first of the three that got into the music industry, and then they were like “D-Dot, you gotta put us on man.” (Laughs) He got his first check from the music industry and had videos playing, and Puff was still dancing in the background then.

DX: You had a hand in Michael Jackson’s #1 hit song “Remember The Time.” What was it like negotiating with Michael Jackson’s camp?

Combat Jack: I worked with Bernard Belle, who was Regina Belle’s brother, and he was a songwriter who worked closely with Teddy Riley. So on the R&B side we were working with Glenn Jones, Bernard Belle — who was the biggest songwriter at the time and co-wrote “Remember The Time.” So I had a hand in helping to negotiate that deal for “Remember The Time.” Of course, Michael Jackson had all the leverage on the planet. But because of Bernard Belle, who was coming in under Teddy Riley, Michael sought out Teddy Riley. You know what I mean? He needed Teddy Riley to make this hot. So we we had leverage, man.

DX: In the transition period of Hip Hop and R&B that became “Hip Hop soul,” what other artists did you help land their earliest deals?

Combat Jack: There was a shift in the last great era of R&B, and it was definitely most of the black music attorneys who were older than me, and they came from the greats of seventies and early eighties era. I was the first born and bred cat from the Hip Hop era. So I was like “Yo, I’m ready for the shift.” We were representing R&B singer Glenn Jones, and this new rapper was trying to get on named (ahem) “Jay-Z.” And none of the labels were trying to sign Jay. And I was like “Yo, Glenn Jones needs a Hip Hop remix. We gotta put Jay-Z on this.” And DJ Clark Kent ended up doing the remix to his song “Good Thang.” We did the deal for Jay to rap on that Shai record “I Don’t Wanna Love You (Remix),” too, because this was the shift from R&B to Hip Hop. And plus it was impossible to get Jay signed. Impossible.

DX: With the debate about “culture vultures” in Hip Hop right now, what was that like being in the board room with record executives who just started budgeting for Hip Hop?

Combat Jack: Back then, the old guard — I’m talking black music execs — they were not fucking with Hip Hop at all. Or they were like “Ok, let’s do this little remix” or whatnot. But we weren’t going to go anywhere. It wasn’t really an “us versus them” thing, as much as an “I’m not going to be listening to R&B all day.” And so it was a matter of just having more fun, the demo’s getting younger, showing and proving. Shout out to the generations before us like the Public Enemy’s, the N.W.A.’s, the Slick Rick’s, and also cats like Black Sheep. They went platinum. It was undeniable — the power of Hip Hop.

So I guess it wasn’t pointing at the “culture vultures” or this and that as much as like seeing the amount of executives who maybe two or three years before weren’t really fucking with Hip Hop. And now they were going out of their way to be down. And I was, “I remember you weren’t fucking with this shit, and now you put on a pair of Timb’s?” But it wasn’t a mystery or anything like that. In a flash of what I just said, there weren’t a lot of black executives. You had a lot of black music departments, which was a great thing because it was like the conversation or the conflict was still amongst us. It was still kind of like a conversation with your family, you know what I mean? It was more like a family dispute about the validity of Hip Hop, as opposed to people appropriating our culture. There was a difference between appropriating our culture, and those that deserved the culture being protective of what this new genre was going to do for the culture.

DX: So when you negotiated these Hip Hop artist’s contracts, and then they got their advances, was it ever a struggle to get your commission checks?

Combat Jack: As a young lawyer, you put a lot of trust in them. But once they get that money in their hand, that shit was damn near impossible to get paid. After two or three deals, you learn about the “Letter of Direction.” Which is when your artist signs that contract, they also sign this letter directing the label to pay you directly your fee. Almost like direct deposit for artists. So it became for me like “I’m not doing this deal unless you sign this Letter of Direction.” It wasn’t a problem, but you can’t depend on muthafuckas to pay you from their pocket.