As we continue to celebrate 50 years of Hip-Hop, this year there’s another significant anniversary that should be acknowledged — the 25 year anniversary of September 29, 1998.

A day that witnessed the release of five Hip-Hop albums simultaneously, all of which most fans consider to be classics. TThese albums were game-changing and helped define where Hip-Hop was going for the next 25 years. That day saw the releases of Jay-Z: Hard Knock Life Vol. 2, Black Star: Mos Def and Talib Kweli are Black Star, OutKast: Aquemini, A Tribe Called Quest: The Love Movement, and Brand Nubian: Foundation. This was a rare day in Hip-Hop where you had good quality releases from rappers who had different styles, perspectives, and sound.

To help me look back on that day, I spoke with veteran journalists who covered Hip-Hop at the time, to find out what they remembered about that release day — the anticipation, how fans consumed the music, and the differences in covering an album release day back then as opposed to now.

Acclaimed journalists Datwon Thomas and Kim Osorio help me look back at that historic day of September 29, 1998.

Where were you in 1998? 

Datwon: I was an assistant music editor at the time for XXL. I might not have even been there one year yet. 

Kim: I was the Associate Music Editor at One World Magazine while freelance writing at The Source and XXL. 

When you think of September 29th 1998 what stands out most to you? 

Datwon: I was assigned an A Tribe Called Quest story, with them coming back, and that was around the time of the breakup and all that stuff. Everybody wasn't sure if Phife and Tip were cool. Then me and Tip got extra cool during that time, and I'm the biggest Tribe Called Quest fan in the world. I don't think there's anybody bigger than me. Maybe Pharrell, you know, somebody named Pharrell might be bigger than me [laughs]. I was just so ecstatic about being able to have chill time with Tip like at the studio, going out to lunch, cracking jokes and just finding out more about him because I was such a big fan from when I was a kid.

I think the other thing we got to remember is that was the year that Jay-Z really broke through and dominated because his album had just dropped. Then DMX had dropped two albums in the same year around that time. So Def Jam was on fire. Then you had Lauryn Hill rocking. Brand Nubian I think is when Grand Puba came back into the group. So that was like a whole thing. Like, oh, we get Grand Puba back. Then Outkast, they’re just solidified. They were coming for the group Crown, which I take Wu-Tang out of, because they're just an anomaly and you have the two greatest groups going at each other in Tribe and Outkast and they dropped on the same day. It's like wow, they're in two different eras of their careers. Like Tribe is on the down because they're not in sync and then Outkast is the hottest that they could ever be outside of Speakerboxxx/The Love Below, which came years later. This is the dope thing about albums when people drop that big altogether. Everyone is at a different point of their career. So you're getting different perspectives on how hip hop should be during that time and I don't think people really realize or register that fact enough. 

Kim: I remember back then feeling like things used to drop on Tuesdays. So they would drop on Tuesdays and we would know when albums were going to drop and we would wait for them. There was a lot of music coming out back then. Before I heard the album, I had been up at The Source hanging out with other writers and I had heard that the album had gotten five mics. I believed in The Source and I knew the editors and I wanted to be down with them. So I believed that was going to be an incredible album because I had already heard that they had given that album 5 mics. So that was a big deal back then. 

How big was the anticipation for that day? 

Datwon: The anticipation for that day was so crazy because since you didn't have the Internet that was able to get to people in mass, you had all of radio. Radio was super important back then. Radio was heavy and then all the snipes in the street was important. That's when you had street teams and you had to get cool with them to understand, like where they're going to be and you see the posters everywhere. They had every lamp post, every gate, all the snipes up on the do not post sign. They was posting in your face. So you got to see the date, who it was and what songs was hitting. You know what I mean? At least in New York it made it like, oh my goodness, I can't wait for this day to drop, you know? 

Kim: I remember meeting Jay-Z back then. That was my first time meeting him around the time when Vol. 2 dropped. He was at a club and all of us were hanging out with the Roc-a-fella crew and I can remember the excitement in New York was very, very Jay-Z. They were outside back then and if you knew what night to go outside, if you knew they would be in the club and which club they were at then that’s the club everybody wanted to be in. 

Out of all the artists who released that day, which one were people most excited for? 

Datwon: I think OutKast, Jay too, but I think OutKast got the edge during that time. Jay was on fire though. That could be true, too. It could have been Jay as well. But yea I would say it’s between those two.

Kim: That depends on where you are. You’re telling me which one people were more excited for, I was in New York back then so it was all about Vol.2 to me. I’m guessing if you were in Atlanta that you were waiting for the OutKast album. 

Hard Knock Life Vol.2 came out and sold 6 million albums and got Jay-Z his first Grammy. Do you feel like that album was a pivotal point in Jay-Z’s career?

Datwon: Yeah, five straight weeks at number one. I don't think any rap album had done that yet. Especially for Jay, for him being such a complex, you know, rich talking rapper. His career seemed singles driven but it's always his albums that hit number one. His singles don't necessarily hit number one. I think "Empire State of Mind" might have been the first one. That just means people want to hear what you have to say as a body of work rather than you're just a singles hit driven artist. Especially back then. Now I feel it's easier for a so-so album to be number one because of the Internet and streaming. Anybody's fly by night album in Hip Hop could shoot to number one, even though we've had a struggle year this year.

Kim: That album was a pivotal point because Reasonable Doubt was very critically acclaimed. But when he released Vol. 1, I remember people feeling like, oh, it wasn't as good as Reasonable Doubt. Then Hard Knock Life Vol. 2  was like this comeback. So he really, you know, kind of married those worlds of like the hardcore underground lyrical side of Jay-Z that he introduced with Reasonable Doubt and the commercial side that In My Lifetime Vol. 1 was seemingly trying to capitalize off of. Vol. 2 was like in the middle of those. So it had just the right amount of everything and it really spoke to the potential of what Jay-Z was going to bring to Hip-Hop. 

Many consider Aquemini to be Outkast’s best album. Where do you rank it and would Aquemini be considered their most critically acclaimed album? 

Datwon: That was probably their best as a unit. I would say that's probably the pinnacle of their group but I think artistry wise Speakerboxxx/The Love Below shows both of their growths individually. Their most critically acclaimed I think is Speakerboxxx/The Love Below because that won the Grammy and I think that might be the last time a Hip-Hop album won album of the year. 

Kim: Aquemini is my favorite Outkast album. So for me it ranks at the top because Speakerboxxx/The Love Below I really love, it's more personal. Like I have a more personal thing with that album. But Aquemini is definitely their most critically acclaimed, it's their five mic album. 

In the 1995 Source Awards Andre 3000 has that legendary quote where he says, “the south got something to say," With the release of Aquemini along with all the success southern Hip-Hop was having that year, could you feel Andre’s words starting to become more true? 

Datwon: Yes. That was a pivotal moment in hip hop as well and I think it was more one where Jay's five weeks at number one was pivotal in showing the growth of the genre. That opened up the door for like the Eminems and everybody else to start having those long runs or being able to sell a million in a week. Andre 3000 really planted that flag and he didn’t implant the flag in the south, he said that at Madison Square Garden and planted the flag right there in New York like “the South got something to say. We here!”. Here's my flag to let you know all those boos are going to turn into oh yeahs. You know what I'm saying? You got to respect dudes for that and he put that on his back. He made it possible for T.I., Jeezy and the rest of them. Even though they didn't rap the same he made it possible for those guys to be able to speak the way that they speak and become the trap masters and kings of the South. Because it was like the South got something to say. You're going to hear us out. 

Kim: Yes, but I feel like when he said it at that time “The South got something to say.” That was a pivotal moment for the South, because that's when we were starting to hear more from the South. Like they really were kind of like positioning themselves to take over Hip-Hop. By 2000, 2001, it was like all about the South. So I think that by ‘98, around that time, it was like they were past this whole idea of, oh, “The South got something to say.” Listen to us. I think people were really paying attention to what was going on in the South in Hip-Hop. So that was a critical year for them. But it was like they were gearing up for a takeover. 

Q: Given that Brand Nubian and Tribe were at the later part of their careers and Outkast and Black Star were in the early stages of theirs do you feel like that day was a passing of the torch so to speak? 

Datwon: Yes because Tribe definitely influenced Outcast. They said that was their favorite group and Black Star, Mos Def, especially Mos Def. He loved Q-Tip and that was their people. So I'm sure they were influenced by them. What's so funny is that Tribe was influenced by Brand Nubian, mainly, mainly Grand Puba, who had already been out from the mid 80’s. Tip was influenced by Grand Puba, his production style and rapping. So the passing of the torch thing I think is a bit different but I do feel as though you got to see a new style of New York and you got to also see a new style of the South really become dominant and here's the difference. Blackstar wasn't necessarily a group to me. It seemed like a collabo that went off. I never really thought that they were going to do multiple albums, even back then, because once Mos did that solo album, I was like, Why is he going back? So the passing of the torch was more maybe Tribe to Outkast rather than Brand Nubian being to Blackstar. I think it was more Tribe saying here’s two emcees that are going to take it to that next level. 

Kim: No, I feel like this particular day with this mix of albums and this sort of diverse offering. I don't feel like it was significant in that space. I'm very big on the eras and what happened at a certain time. So I feel like about ‘95, ‘96 the sounds of Jay-Z on Volume two had taken over completely. Right. So it was leading the charge and the Brand Nubians and the Tribes and what we would call at the time conscious hip hop had peaked already in the early to mid 90’s. So for them at this time in ‘98, they were serving a very select but a core audience that had grown with them. They'd never been the type to try to please that bigger mainstream audience, whereas Jay-Z with Vol.2 like that was more where hip hop was at that time in ‘98. 

Q: Not only was Mos Def on the Black Star album but he was also on Tribe’s The Love Movement. Back then could you see that Mos Def was special and that he would be an artist people would love and revere to this day? 

Datwon: I don't think people realize how dope he is. We always have these lists where everybody's like, Oh, the underrated rappers are always like, Kool G Rap, AZ and Black Thought. They always put the guys that have like incredible wordplay but maybe not have like those super big hits but their albums are dope and solid. Mos Def is different. He doesn't even want the super big hits. It's not even a thing for him. His thing is about a vibe, educating his people and showing how nice he is on the mic. He also just enriches emotion. It's not like he pulls it out of you. He enriches it. Whatever he feels. He puts like this magic dust on his shit that makes you like, damn man, how could someone's thought pattern weave shit together like that over such incredible music? And I love him when he's against live music more than beats.

Kim: Mos Def was very skilled but he also had like incredible flow. I think people respected that. I remembered he was revered by people in Hip Hop. When he came out, remember, he was on the cover of The Source early on.

Q: How different was it covering a release day back then as opposed to now? 

Datwon: Super different. You would plan for, like, weeks. You know what I mean? Now everybody just drops, and you don't get to talk to them because they're talking to the people on social media. Plus you don't get advanced listens to albums anymore, it's really rare. They don't really throw the major albums out there because everybody’s afraid that it's going to get leaked. The hip hop albums that I get that are major is because I have a relationship with those people. You don't necessarily see like, Yo, I listen to this album and here's how it goes kind of reviews anymore or previews anymore. You don't really get to see those. You know what I mean? Not of significantly big name artists. It just doesn't happen.

Kim: Release dates don't feel as important nowadays as they did back then. Everything was about building to your release day in the late 90’s. Now It's like you'll see something and it'll be like dropping Friday and it's like Wednesday. You know what I'm saying? Like, hey, “dropping new album Friday. In two days!!!”. But I feel like in the late 90’s the hype was built up for months. 

What did promotion for those albums look like and how different was promo back then as opposed to now? 

Datwon: Promo back then was like a trip to their favorite location. You could be on an island somewhere with an artist because the label's flying everybody out. You know what I mean? And putting everybody up showing all of us incredible life experiences with a body of work. That's the biggest difference. Also, you used to get these promo items. They used to come in these big boxes and everybody was trying to outdo the other person with their promo albums. The listening parties for these albums were epic. I'm talking about they're playing new music and then all these celebrity friends that might rap, they will be there. Like for Jay, I think for Hard Knock Life, yo it was so crazy. They had it at Sony Studios and man oh man. Yo, everybody was in there. It was like little cyphers going on on the side and those types of things were happening. Now, my mind you, of course, these album things happen now, but everybody's like, getting ready for the IG’s, photos and shit. You know what I'm saying? Like they’re primping and prompting. You know a lot of times our everyday life was Monday to Thursday we party after work, you're going to somebody's event and every other night is somebody’s listening event. Now it’s like, pretentious a little bit. I don't want to sound like the jaded old man within this, because I'm really not that. I'm just telling you the difference between the two experiences now.

Kim: There was always like a single that dropped early and then there was a single that was followed up. So you had at least two tracks that you've already heard from the album before it dropped. And I felt like labels had the street team and the street team was marketing or they're throwing up stickers and stuff all over the city. 

How much did it help having networks like BET and MTV play music videos back then?

Datwon: It helped tremendously. That's all day promotion. At the top of each hour, just like radio, it was going to play the new video. You had buildup. You had million dollar videos. They don’t have million dollar videos anymore. You wanted to see how they spent that million dollars. You wanted to see what kind of new effects Hype Williams or Little X or Paul Hunter had. What the outfits were going to be like, what the choreography was going to be, what the location was going to be like. Videos meant something, man. It was like the visual component to whatever artistic offering you were given sonically. You had to love that. So BET was tremendous because they played videos that MTV wouldn't. BET made certain songs that would have never been hits, hits. Whereas MTV was just going for like, who's the biggest star in hip hop or R&B, and let's go with them. They weren't playing everything like how BET was. 

Kim: Video promo back then was so important to an artist's promotion of their album. Those of you know that at labels there was a whole department dedicated to just that. Outlets like BET; shows like Rap City, MTV. These were vehicles to push and promote the artist's albums and the visual component was so important to us because we didn't have social media back then. This was like the first time you're really seeing the artists in their element a lot of times, especially for new listeners. So yeah, I feel like a video was almost like a benefit. Right. Like if you got a video it’s a big deal for a song. Around this time I feel like music videos were really the driving promo, right. That television look, you couldn't do much without having the support of an MTV or BET’s Rap City. So it was very important, especially in the late 90’s. 

How much of a factor did radio play when it came to big release days like September 29, 1998?

Datwon: Radio was paramount. Because this is the other thing about radio. You might not be getting played on BET and MTV, but if radio got you, you can go get some sales. More than likely, though, if you were being played on MTV and BET then you were getting played on radio. So, radio played that step in the gap. When they say video killed the radio star or whatever if you wasn't getting played on MTV or BET, if you're local, if you were a local rapper, at least your local radio station is going to play out of love and that can get you some sales. So they were imperative to the whole paradigm of everything music, especially in black culture. And I still believe that they're important today too.

Kim: This is hard. I think these questions are better suited to executives who were driving campaigns, right? What we did as writers and as tastemakers, we were important to like the forecasting of music. So we would hear the music. We would judge the music based on what we heard, based on what we knew of the artist, the anticipation that we had for release. Right? But the radio, the video, like all of that stuff, those components, if you worked at a label like they were so important to the release of a song. The label will be able to tell you. Was radio important? Yes, like you need a certain amount of spins. I don't know all of that stuff, when we start talking about radio and radio promo I think that's a conversation that would be better answered by record execs. 

With the variety of releases that day would you say Hip-Hop was the most balanced at that time?

Datwon: Yes, I think Hip-Hop in ‘98 going into' 99, maybe even 2000, you probably had the best representation of north, south, east, west, Midwest. You had the best representation because remember, you're ‘98, ‘99, you're still getting like Master P, you’re getting Common, still getting Ice Cube and all of them on the West Coast. Snoop and everybody. Pharrell is starting to really come up in the game. Timberland is rocking. UGK still going. New York is still trying to hold on to their dominance in the clubs because the clubs are very important. In ‘98, you've got the Tunnel and all of that stuff. Like if you were doing certain clubs in certain cities that's how you would get on to. So yeah man, like that was definitely the shit. 

Kim: You know, that is a good time to say that it was balanced. That's a great perception about ‘98. Like if you think about ‘98, one of the strong points to that year was the balance that you had in Hip-Hop, right? The different types of hip hop, the subgenres, diverse offerings.. You've got like a certain amount of underground and commercial and R&B meets hip hop. That could be like if you were you and you were writing the story, you could make an argument for ‘98 being in that day with those releases being the most diverse day in hip hop, right? Yeah, because I can't think off the top, like another time. It was a good year for Hip-Hop. I think it was a good year.

How would you compare September 29, 1998 to other legendary release days like November 9,m 1993 or September 11, 2001 or September 11, 2007? 

Datwon: I think the 29th is the bigger day out of all of them, but I think the most significant is probably September 11th because Jay dropped that day, still did crazy numbers and that wasn't even without streaming and stuff. So people were really heartbroken and all messed up about 9/11, but they still went out and got records. Shits crazy. And you don't know if that was therapy or whatever to get people through. But it was still significant enough that they went and got that album that week. 

Kim: So I would say these are like significant days in the release of classic Hip Hop albums. So it's interesting because I don't think people are as familiar with the day that things drop. But if we start to think about it like that, they were definitely driven by, you know, the release or the clash of the titans. I feel like that's what we called it. The Kanye and 50 Cent drop that day was Clash of the Titans. So the albums and the promotion was marketed in and of itself. You know what I mean? Like, Oh my God, these two albums are dropping on the same day. It ended up making the fact that two albums are dropping on the same day a marketing ploy. So it's really interesting when you think about the release days and what they meant back then and how today's releases don't really fall in line with that type of thinking. The way fans consume music is different. The way that the narrative drives more of the success of a release now than the actual release date. It's a different time, but back then. Yeah, It was something to watch when the days came up and you built towards those release days. That’s when you really anticipated the release of a record. 

Is September 29th 1998 the last true Hip Hop release day? 

Datwon: No, I don't think it's the last true hip hop release date. I think it's just one of those legendary things that happened in hip hop where you're like, wow, this is super incredible. I think of Kendrick Lamar's first album as like a landmark. I think some of Drake’s release days are significant. Think about it. After that date [September 29th 1998], it became a thing. Maybe a couple of years later, but it became a thing. “You better move your release date,” and people were moving it around when big artists we dropped. That's why the Kanye 50 thing was such a big thing. Because normally if an artist like Kanye didn't have the kind of respect and internal ego shit he would’ve been like “50 Cent is about to drop, let me move my date.” So you didn't get those days like that anymore where artists were like, Fuck it, let's all drop that day because they will all be in a record store and everybody will go get it. But as time goes on, you didn't have to go to the record store to get albums. You could just go get what you want and it doesn't make a person grab another album while they're in the store because they're not in the store. So those days can't happen like that anymore with the whole new way of culture of “Imma let such a such get their day.” And now I don't have to go to the record store to go get shit. So it is one of the last days, but I feel like there were other great days for releases. 

Kim: I don't think it's the last true release day because I feel like there's other important release days that matter after 1998. I feel like when you talk about days like September 11th, 2007 and all these other dates that you mentioned, these are big drops, right? And so, I wouldn't call it the last true release day.