September 29, 1998, might as well have been Christmas Day for rap fans. On that fateful Tuesday, record stores stocked their shelves with no fewer than five must-cop hip-hop releases—two soon-to-be classics (Jay-Z’s Vol. 2… Hard Knock Life and Outkast’s Aquemini), a breakthrough debut (Black Star’s Mos Def & Talib Kweli Are Black Star), and two albums from legendary groups (A Tribe Called Quest’s The Love Movement and Brand Nubian’s Foundation). Twenty years later, it is still remembered as the greatest rap album release day ever.

But was it? In today’s age of staggered drops and surprise albums, when Spotify and Apple Music have rendered Tower Records and HMV obsolete, the idea of a crowded music release day feels quaint. Yet there was a time when if you liked rap and had limited disposable income, every Tuesday presented some difficult buying choices. Two old(er) Ringer staff writers reminisced over rap’s biggest release days over the past 30 years to determine whether 9/29/98 was truly the best one.

Donnie Kwak: I don’t know whether this is true for you, Shea, but visiting a record store to rummage through vinyl (when I was super young) or cassettes (elementary through middle school) or CDs (high school, college, and beyond) was a formative part of my music fandom. Rather than passively waiting for an album to leak online or appear on a streaming service, this was an active experience that felt deliberate and meaningful. I literally couldn’t afford to choose a wack album, so every decision felt weighty. Which is why any release day that presented more than one viable option felt like Sophie’s choice.

Shea Serrano: Wait, Donnie, how old are you? Are you a billion years old?

Donnie: [Triggered.] Was it the “Sophie’s choice” reference? Let’s just say I’m old enough to have bought Purple Rain, with allowance money, on vinyl. Shout-out to Variety Records in Wheaton Plaza.

Shea: I don’t know who wrote that italicized intro up there but I would like it stated for the record that I am not one of the “old(er) Ringer staff writers.” I just turned 24 this past summer, thank you. Everybody knows this about me. People are often saying how young I am, because I am so young.

At any rate, what was the first music you remember buying with your own money and being very excited about? Mine was “Gangsta’s Paradise” by Coolio. I remember being really excited about it because I was really excited about the movie Dangerous Minds, and they were using that song in the trailer for Dangerous Minds. It was this whole package, it felt like. Because you had the song, and then you had the movie, and then you had the video, which actually had Michelle Pfeiffer in it as her character from Dangerous Minds and she was talking to Coolio and he was rapping at her and it really just blew my fucking mind. I’ve always been a big, big fan of when different parts of different things get folded over onto each other (like when Will Smith had that song with Freddy Krueger, or when Boyz II Men were on The Fresh Prince of Bel-Air with Will Smith, or when Will Smith did the “Men in Black” song for the Men in Black movie, and also various other non–Will Smith examples). So I remember seeing all of that, and then deciding after my mom wouldn’t give me any money, “Yes, I need to go to the mall and shoplift this tape from the store.”

Donnie: As far as rap goes, I’d say the earliest tape I remember being excited about was Run-D.M.C.’s Raising Hell—and in particular, this song. But that’s going way back to the mid-’80s, which is a bit too far for the purposes of this exercise.

Shea: What are the purposes of this exercise?

Donnie: To determine the best rap album release day ever. It wasn’t really until the late-’80s, when rap music became less of a niche and more of a profitable music genre, that the idea of a “rap album release day” really took form. To that end, our trusty intern Austin Elias-de Jesus compiled a list of notable release dates over the past 30 years. The first entry on that list is June 28, 1988, the day when Public Enemy released It Takes a Nation of Millions to Hold Us Back and Big Daddy Kane dropped Long Live the Kane. Powerful impact, both. But if we’re trying to best the riches of 9/29/98, we probably need to have a minimum of three notable releases on a given day. Or maybe not, since that would rule out September 11, 2007, which is probably the last notable rap album release day—who could forget Kanye West vs. 50 Cent? So, Shea, do you think we need to set some parameters here? Is it quality or quantity that should be the focus?

Shea: There definitely needs to be a set of guidelines here, but I don’t think it has to be anything too complicated. I think you need four things. You need:

At the very least, two unforgettable albums that were released. The Kanye vs. 50 Cent thing is a good example. That 50 album (Curtis) was not so great, but it still goes down as unforgettable because of the moment that it was wrapped up in. At the very least, one album that was very good but not quite unforgettable. We’re looking at something that’s on the same grade level as, say, Fabolous’s Ghetto Fabolous from 2001. At the very least, one album that was underrated then and remains underrated now. Something close to Juvenile’s 400 Degreez, which helped shape the South’s identity as a powerhouse in the late ’90s, or Missy’s Supa Dupa Fly, a top-level classic album so good that, even if one of its songs became the new national anthem, it’d still be underrated. At the very least, one album that, looking back at it today, clearly holds some sort of historical significance. It doesn’t even have to be a good album, really, just one that you can point to and go, “Here it is. This is when things either changed, or started walking toward change.” A good example would be Eminem’s Infinite album from 1996. It definitely was not good, but it’s impossible to argue that the official arrival of Eminem—even three years before he became a cultural shift—was in anyway insignificant.

And to be clear, this equals up to five total albums, but we don’t actually need five albums. One album can satisfy two or three categories, really. Like, Mos Def’s Black on Both Sides album could satisfy nos. 1, 3, and 4, you know what I’m saying?

Also, if there were two albums that came out on the same day that were undeniably gigantic and influential and massive and unstoppable, then you can wash away everything I’ve just said and go with that.

Donnie: Right. All of your criteria makes sense. (By the way, Ghetto Fabolous came out on the same day as Jay-Z’s The Blueprint, which also happened to be September 11, 2001.) I should add that “rap album” here refers only to actual, official albums that one could buy in a store. Meaning no mixtapes or weird “best of” bootlegs are eligible. Furthermore, I’d add that if we were to extend this exercise to encompass all genres, then it’d be hard to top September 24, 1991: Tribe’s The Low End Theory, Nirvana’s Nevermind, and Red Hot Chili Peppers’ Blood Sugar Sex Magik. I digress.

Shea: Nothing says “fun” like a lot of rules to follow.

Donnie: Parameters prevent anarchy, Shea.

Shea: So, assuming we’re operating under the assumption that, as it stands now, September 29, 1998, is the reigning Rap Album Release Day champion, let me toss a few at you that might be able to topple it. I’ll start with a recent one that was very good: August 3, 2018.

Here’s what we got on that day: There was a new YG album, and YG is probably one of the six most interesting rappers in existence today. There was perhaps the most well-received album of Mac Miller’s far-too-short career. There was Travis Scott’s oddly intriguing Astroworld, which I suspect will age very well (and which also has enough regional punchiness to make it compelling beyond its own narrative). And there was an Iggy Azalea album—as much as we might fight against it, I don’t think there’s a way to talk about Iggy without mentioning that she was, even for the briefest period (and possibly for many wrong reasons), one of the most popular rappers on the planet. That sort of hold can’t be ignored, even if it’s only acting as a negative thing.

Donnie: Yikes. I don’t disagree that there were a couple of good releases on that day, but it’s nowhere near challenging 9/29/98, not even close. (Would you pay $15 for any of those albums? Maybe Travis. You could, however, pay me $15 and I might listen to the Iggy album.) Anyway, my first contender goes to September 22, 1992. You’ve got Da Lench Mob’s Guerillas in Tha Mist (category 3), Showbiz & A.G.’s Runaway Slave (category 2), and then the debuts of Diamond D and Redman (category 1). The other date that instantly stands out to me satisfies the “undeniably gigantic and influential and massive and unstoppable” corollary: Wu-Tang Clan’s Enter the Wu-Tang (36 Chambers) and Tribe’s Midnight Marauders both came out on November 9, 1993. Hard to top that.

Shea: I suppose the problem we’re going to run into with any newer release dates is, short of something as mammoth and intentional as Kendrick Lamar’s To Pimp a Butterfly, we don’t know the kind of historical impact an album might eventually end up carrying. Also: I can’t believe you wouldn’t pay $15 for YG’s album. That’s wild. YG is incredible.

The November 9, 1993, entry is an extremely solid selection. Both of those albums are surefire first-ballot Rap Hall of Famers. Each of which is an early ’90s work that, after Dr. Dre and his friends pulled the center of rap toward the West Coast, bent rap back toward where it started.

But if we’re going to talk about release dates that had two albums that could stand taller than the five albums listed for the September 29, 1998, entry, I’m going with February 13, 1996. We got All Eyez on Me, the last-ever album from a living 2Pac (and also his best one), as well as The Score by the Fugees, which still is impacting what music sounds like today.

Can that date beat the September 29 one?

Donnie: Good choice. I should also note that All Eyez on Me is a double album, which essentially makes it seem like we got two Pac albums that day. (Get it? Two … Pacs.)

Shea: Donald.

Donnie: I also appreciate the juxtaposition of the two albums—while Lauryn Hill and Wyclef were decrying that era’s obsession with Italian mobsters, Tupac was fully embracing the Gambino lifestyle. Point, counterpoint. To beat the incumbent, though, I think we’d need a third good-to-great album to have been released that day, and I don’t know whether [squints] Mad Skillz’s From Where??? fits the bill. (Decent album, though.)

I’m a little partial to May 14, 1991, when the following albums dropped: De La Soul Is Dead, which was (at the time) avant-garde; Ice-T’s OG Original Gangster, which was peak gangsta rap; and K.M.D’s Mr. Hood, which was a cult classic. I’m still having a hard time topping September 29, 1998, though, just because of the diversity of options: One upstart (Black Star), two monsters in their prime (Hov and Outkast), and two aging HOFers (Tribe and Brand Nubian). It would be something like if Juice WRLD, Drake, Kendrick, Nas, and Lil Wayne all dropped albums on the same day this year.

Shea: It’s the Jay-Z part that’s making this impossible. He is, one could legitimately argue, the greatest rapper of all time. If we take him out of the set of albums, finding a more impactful rap release day becomes considerably more reasonable. But I guess that’s like saying the Bulls were easier to beat without Jordan, which is a thing so obvious that it’s not even worth saying.

OK, let me offer one last one here, and this is a Hail Mary attempt, but: What about September 13, 1988? Four big albums came out that day. There was Ice-T’s Power. There was Eazy-E’s debut solo album, Eazy Duz It. There was MC Lyte’s Lyte As a Rock. And there was Steady B’s Let the Hustlers Play. This group of albums has the opposite feel of the September 29, 1998, one. Ice’s album was a follow-up to his wildly controversial (and wildly important) first album, Rhyme Pays; Eazy-E’s and MC Lyte’s albums were debuts, and Steady B is an unfairly forgotten architect of gangsta rap. So you could point at that bunch and very fairly say: Three of these albums went on to hold a substantial place in rap’s history, as did all four of those artists. If you’re looking for pivot points in rap, this has to be one of them.

Is it enough to overthrow September 29?

Donnie: We’re on the same wavelength. In terms of diversity, historical impact, and depth, that day and its releases are probably the closest contender to 9/29/98. (Funny how that date also fell in September, one decade prior. September has historically been a boon month for music.) Still, I think it falls just short. Put it this way: If you were marooned on a desert island and could take with you only rap albums that were released on the same day, you’d have to choose 9/29/98. You’d get ignorant Hov in his prime, an undeniable Outkast classic, Black Star backpack rap, some of J Dilla’s best beats on The Love Movement, and finally, a dash of Sadat X—maybe my favorite underrated rapper—on Foundation. Every hip-hop itch would be scratched. So, yes—September 29, 1998, is indeed the best rap album release date ever. I can’t imagine it ever being overtaken—but not for lack of trying.