'I'm Still Spending Money from '88': 9 Thoughts About Jay-Z's Reasonable Doubt, One of the Best Albums of All Time on Its 25th Birthday

Jay-Z’s damn near flawless debut album, Reasonable Doubt—arguably one of the greatest debut albums in hip-hop history—was released 25 years ago, today, on June 25, 1996.

Since I truly began listening to the album, it has been in my top 10 favorite albums. And I have to say “truly began listening,” because like many New York City classic albums, I was late to that party. But any album as seminal as Reasonable Doubt, which launched one of the greatest careers in any discipline, needs some revisiting, and I figure the best way to do that is to list 9 thoughts I have about the album 25 years after its release.

1. My first exposure to Jay-Z must have happened in like ’93. I’d never seen (or even heard of) “Hawaiian Sophie” until after Jay was a thing. Nope, I first saw him in the video for “Can I Get Open?” from the group Original Flavor, which featured producer (and rapper) Ski—who would go on to produce four records on Reasonable Doubt— and was managed by Damon Dash.

I just wanted to point out that I vividly remember Jay from 1993 and simultaneously forgot about him wholesale after that video moved out of rotation on BET’s Rap City. This is important because while I genuinely liked that record and Jay on it, I didn’t in any way view Jay as this could-be-legendary act. I was also 14 at the time and maybe not the best A&R, but in my mind there was no way that version of Jay—the double time-rapping Jay—could become the Jay who would become arguably the GOAT rapper. Was the talent there? Of course, he made a name in NYC because of it, but I couldn’t see a whole album of that becoming Reasonable Doubt and then, well, Jay’s career. With Nas, it was damn near apparent immediately; Jay more or less showed and proved.

2. This also is interesting because Reasonable Doubt came out during the summer between my junior and senior year of high school. When I got back to school, my boy Jerard—one of my closest friends in life—would not shut up about this dude Jay-Z (who I absolutely did not recognize as the dude from Original Flavor, smh) and his album, Reasonable Doubt. Specifically, he loved the song “Politics As Usual.” For the entirety of my senior year in high school, Jerard would ask me damn near daily in our AP Calculus class (it must have been our first class of the day) if I’d checked out Jay yet. He was the first person I knew who wouldn’t stop talking about Jay-Z (and it continues to this day). That would carry over into college—we went to Morehouse College together. I never did listen to Jay, at all actually, during my whole senior year of high school. In fact, it wasn’t until that next summer, before entering Morehouse, when I was at my older sister’s house in Atlanta and I saw a CD on the floor, asked what it was and she and her boyfriend at the time were like, “Yo, you need to get on this Jay-Z!” They gave me the CD. I loved it from that day on.

3. Because no convo about Reasonable Doubt and Jay truly exists without the infamous, “who is the greatest, Biggie, Jay-Z or Nas?” line pondered in “Where I’m From” from In My Lifetime, Vol. 1.?, I am going to go on ahead and admit some things: I’m a bigger fan of Reasonable Doubt than I am of Illmatic and Ready to Die, two albums that are classics, though Illmatic is often considered to be the GOAT hip-hop album. I get it, but I almost never listen to Illmatic whereas I listen to Reasonable Doubt, even in the year of our lord 2021, many, many times a year. And let me take it a step further: I kind of don’t even like Ready to Die that much. *whew* I feel better; I’ve never written that out loud before. Despite the supreme darkness of Reasonable Doubt, I find it a much more entertaining and enjoyable listen than both of those albums. And I enjoy the bars more. Personally.

4. “Can I Live” has been one of my favorite hip-hop records since 1997 and is still as good today to me as it was then. Jay’s bars on that song, plus the sample, plus his general nonchalance make for one hell of a record. I love that song so much I can’t even listen to “Can I Live II” as like a part 2. It needs another name. I fucking love “Brooklyn’s Finest” with my whole heart. It’s a damn clinic of lyricism between two of the best to ever do it; for the record, I think Biggie is the GOAT lyricist, even despite what I said about not loving Ready to Die. I know I contradicted myself; look, I don’t need that now. I actually didn’t, but some of you will see what I did there. You are my people.

5. One of the most amazing things about this album, aside from his outstanding bars is really how detached from morality Jay is on the album. That version of Jay, if he ever really existed, is absolutely not the same Jay of today. And that’s a good thing, obviously. It’s just amazing. When you listen to songs like “D’Evils,” “Do Or Die,” or well, a significant portion of his catalog, that detached, business-never-personal singular focus is almost scary. And it’s amazing that even listening to it now how there are lines and verses where I’m truly wondering who in the fuck that dude was. I suppose that’s why he “came into this motherfucker 100 grand strong, nine to be exact, from grindin’ G packs.” He told us he had a hustler’s spirit, and I suppose, perhaps, that was what kept him alive.

6. Which is what makes the ability to follow the trajectory of an individual, not only through an album but through life, and to see those changes and how they impacted him, so fascinating. Like, we probably know more about Jay’s life than most rappers, maybe because of Beyoncé—not even maybe, actually—so seeing him go from this drug-dealing rapper who seemingly didn’t give a fuck but was too cool to really ever give a fuck to being a father and one who makes 4:44, albeit as a mea culpa, is truly a marvel. 4:44 has all types of vulnerability on it. I know Jay feels a supremely personal connection to Reasonable Doubt—evidenced by all of the damn lawsuits he’s bringing against folks related to it these days—as it was his first album and his baby, but I also wonder how he feels listening back to it now and reflecting on the man who made that album.

7. I don’t know if this is controversial or not but aside from maybe “Brooklyn’s Finest,” I don’t actually believe he didn’t write this album with a pen and paper. For the remainder of Jay’s career, it seems like his whole steez has been flow based. That is not the case on most of the songs on this album. There are times when he’s trying to get all the words in a bar, where he starts off in a way that you ONLY start off if you’re working from a notepad. Like, “Coming of Age,” I just don’t believe that’s not written. Or “Politics As Usual,” which is so fucking amazing, beeteedubs.

8. While I didn’t see it from my first exposure to Jay, it makes a lot of sense that he, with his talent, is a legendary hip-hop artist. He has the back story, the classic debut album, the career, the mythology (so many stories surrounding Jay), he came up in the ’90s early hip-hop game and lasted all the way through the current day and morphed many times to adapt with the times.

And Reasonable Doubt, as a body of work, as a piece of music, is the kind of album that sets the stage. The fact that he and his whole camp were on some “one and done” (Reasonable Doubt was famously supposed to be the only album, verified from all types of sources like DJ Clark Kent) but he had to go back and keep making music just lets you know, at least in hip-hop circles, how the album was viewed. Commercially it took forever to move units, but in hip-hop, I think Jay had no choice but to become the artist he is; sometimes you’re just too good to not be who you are. Also, as a sidebar, I think that’s why so many artists nowadays won’t become “legends,” so to speak, in the genre. There’s no backstory, there’s no classic albums, and maybe this is an oldhead placing my standards on a genre that has changed entirely. But will artists who impact now, like Lil Baby, be relevant 20 years from now? I will be very surprised if they are.

9. I’m a Reasonable Doubt over The Blueprint guy, for the record. Both classic records, obviously, but Reasonable Doubt just hits me differently. I can’t say Reasonable Doubt is better, necessarily, but the word play, the construction, the feel and the samples are more my speed. I only bring this up because this is one of the debates I’ve been having fairly constantly since 2001, when The Blueprint was released. It just seems like something that would need to be shared. And sharing is caring. You’re welcome.