1990s Hip-Hop: An Album a Day

Featuring Outkast, Missy Elliot, Mobb Deep, and others

My friend Ken and I decided to listen to an album every day this year. Each week is themed. At the end of each week, we rank what we listened to. To be clear, we aren’t ranking every album that fits the theme. We are only ranking what we chose to listen to during the last seven days.

This week’s theme is “1990s hip-hop,” meaning rap albums released in the 1990s. Between our weeks listening to diss albums and rap groups, we’ve actually listened to a good deal of hip-hop this year. That said, this week showed the strongest representation from the genre—MC Hammer aside.

---

#7 Please Hammer Don’t Hurt 'Em by MC Hammer (1990)

When Ken and I listened to The Message by Grandmaster Flash and the Furious Five a few weeks ago, we were a bit shocked. For an album by a rap group, there were a surprising number of tracks that did not involve much rapping. I came to learn that early in hip-hop’s history, rapping was seen as a bit of a novelty. Thus, many early albums in the genre contain various R&B and rock songs (e.g., “Takin Care of Business” by Kurtis Blow).

MC Hammer falls firmly within this bygone tradition. Of course, he raps on tracks like “Lets Go Deeper” and “Crime Story,” but the album is littered with covers (e.g., “Have You Seen Her”) and quasi-reimaginations (e.g., “She’s Soft And Wet”). This is not a problem in the abstract. Many albums are littered with covers and quasi-reimaginations. The problem is that MC Hammer’s covers and quasi-reimaginations and horrendous.

Nearly every track on this album is derivative in the worst way possible. “U Can’t Touch This,” the album’s only classic, is a prime example of this. It’s just some lazy rhymes over “Superfreak” by Rick James (e.g., “Fresh new kicks, and pants / You gotta like that, now you know you wanna dance”). Even when Hammer tries to do something original, like on “Black is Black,” he doesn’t have the skills on the microphone to carry the song.

Yet Please Hammer Don’t Hurt 'Em sold ten million copies in less than a year. Ten million copies! Only 53 albums sold that many copies in the era of physical media. Why? How? I actually got the answer when my wife entered the room while I was listening to this travesty. Usually when I am playing music, she enters without a comment. But with Hammer bumping, she danced her way in to the room. Get the ladies dancing, and you’ll sell a lot of records.

#6 The Coming by Busta Rhymes (1996)

As a child of the 2000s, I’d always thought of Busta Rhymes as the mile-a-minute rapper on tracks like “Break Ya Neck.” Busta was not moving with that speed on his debut album, The Coming. His voice was still compelling and playful. On songs like “Woo Hah!! Got You All in Check” you could almost compare him to a circus ringleader.

But since his flow was so much different than my expectations, I ended up not enjoying the record as much as I would have liked. Of course, that’s not really Busta’s fault. But I must speak my truth.

#5 Only Built 4 Cuban Linx... by Raekwon (1995)

I’ve admittedly never gotten very into Wu-Tang Clan. Frankly, I find some of their work more impenetrable than I should for a popular act. But Wu-Tang is unique: a ten piece hip-hop team where each member somehow remains distinct. Pair that setup with beats equally likely to be sourced from old soul songs and kung fu movies, and you get one of the most unique hip-hop groups in history.

Only Built 4 Cuban Linx... is firmly within the Wu-Tang lineage. Being billed as Raekwon record would be enough to join that blood line, but with RZA producing every track, Ghostface Killah appearing on nearly every track, and the rest of the Staten Island clan popping up throughout the project, it’s a Wu-Tang Clan project in all but name only.

Of course, there are differences. Raekwon leaned heavily into his mafioso personality on this album, popping bottle after bottle of Cristal while—in the words of Jonah Bromwich from Pitchfork—writing “paeans to those hardworking souls ducking RICO charges.” Because of that, Only Built 4 Cuban Linx... is equal parts glitz and grit. Just a few bars from “Incarcerated Scarfaces” illustrates this dichotomy:

But all I need is my house, my gat, my Ac'
Bank account fat, it’s going down like that
And pardon the French, but let me speak Italian
Black stallions wildling on Shaolin
That means the island of Staten
And niggas carry gats and mad police from Manhattan

#4 Southernplayalisticadillacmuzik by Outkast (1994)

Though many would make the case that both André 3000 and Big Boi are two of the finest emcees in hip-hop’s history, their respective skills on the microphone are not what keep me coming back to Southernplayalisticadillacmuzik and the rest of their catalog. It’s the musicality.

I will mention something similar when discussing Supa Dupa Fly, but in a genre so heavily built around words, it’s easy to coast by on basic beats. Just set the drum machine to a preset, chop up an old funk song on top, and tell a story. Southernplayalisticadillacmuzik does not rest on that. You’ve got singable choruses on tracks like “Player’s Ball.” You’ve got Eddie-Hazel-esque guitar solos on tracks like “Funky Ride.” And, of course, you’ve got bars on bars on tracks like “Git Up, Git Out.”

Much of this is the work of the production trio Organized Noize. But André 3000 and Big Boi’s contributions should not be discounted, especially when we know where their career was headed.

#3 The Infamous by Mobb Deep (1995)

It would be easy to highlight the thematic similarities between The Infamous and Only Built 4 Cuban Linx... Both capture grim tales of street life. But, as noted, Raekwon’s characterization is just as much glitz as it is grit. Mobb Deep has no time for glitz.

If Only Built 4 Cuban Linx... and The Infamous were both films rather than albums, the former, while violent, could be some escapist fantasy. The Infamous doesn’t play like that. It’s a documentary narrated by Prodigy and Havoc, the rhymes telling the story but the grim beats setting the stage. I challenge you to listen to tracks like “Survival of the Fittest” and “Shook Ones, Pt. II” and not feel like you’re being followed.

#2 Supa Dupa Fly by Missy Elliot (1997)

Compare the lyrical sample I just shared from Only Built 4 Cuban Linx... to this sample from the title track of Supa Dupa Fly:

I feel the wind
Five, six, seven, eight, nine, ten
Begin, I sit on hills like Lauryn
Until the rain starts coming down, pouring

This example is representative of the fact that Missy Elliot is not as skilled a rapper as André 3000 or Raekwon or Prodigy. Her rhymes aren’t as dense. Her wordplay isn’t as deft. But what Missy lacks in technical skill, she more than makes up for in other ways.

Missy Elliot’s bars are filled with swagger. In the male-dominated world of hip-hop in the 1990s, a woman rapping, “I was lookin for affection / So I decided to go, swing that dick in my direction / I’ll be out of control / Let’s take it to perfection / Just you and me” was shocking. Missy Elliot is compelling.

And then there are the beats. Missy paired up with a young, mononymous producer named Timbaland to produce Supa Dupa Fly. Whereas many rappers in this era were sampling well-known hits (e.g., MC Hammer) or creating simple, repetitive loops to pontificate over, Missy and Timbaland were turning, in the words of Entertainment Weekly, “avant-garde sounds into No. 1 hits.”

A track like “Izzy Izzy Ahh” is a great example of this. Missy manages to transform nonsense into frightening boasts (e.g., “Izzy-izzy-ah-zi-zah-zi-zah-zah / Hard bitches be talkin’ like they rah-rah / Blizzy-blizzy-blahzah-blahzah-blahzay / None of y’all fools ain’t got shit on me”) while Timbaland cooks up a sparse, sinewy beat.

#1 Capital Punishment by Big Pun (1998)

Not long after college, I fell in love with The Postal Service’s album Give Up. The collaboration between Ben Gibbard, Jimmy Tamborello, and Jenny Lewis sounded like nothing I’d ever heard before. I was excited to have a new discography to dive into. The excitement didn’t last long. I soon realized that The Postal Service only released a single album. I was upset. Big Pun left me feeling quite the same.

Before clicking play on Capital Punishment, I wasn’t familiar with Big Pun. But moments into the first track, “Beware,” I was enthralled. Seldom have I heard an emcee stack so many rhymes on top of one another. Here’s a few fiery bars from “You’re a Killer” that illustrate this:

Big Pun’s my thug’s name, bustin’ my guns, that’s my love thing
I’ll slit your jug’ vein and snatch your Adam’s Apple
John Madden-tackle your corpse to hoist it on a cross at the tabernacle
That’ll have to hurt, I’ll work your body ‘til it burst

I needed more Big Pun in my life after hearing Capital Punishment. Sadly, there wasn’t that much more to listen to. The Bronx rapper was dead two years after releasing his debut. He’d struggled with his weight for most of his life. When he had a heart attack at 28, he was almost 700 pounds.

I can’t pretend that Capital Punishment has the beats of Supa Dupa Fly. I also can’t pretend that it has the hooks of Southernplayalisticadillacmuzik. I’m not sure it even matches the storytelling of The Infamous. But Pun’s dexterity on the microphone will leave you asking “What if?” for years to come.

---

Shout out to the paid subscribers who allow this newsletter to exist. Along with getting access to our entire archive, subscribers unlock biweekly interviews with people driving the music industry, monthly round-ups of the most important stories in music, and priority when submitting questions for our mailbag. Consider becoming a paid subscriber today!

Recent Paid Subscriber Interviews: Pitchfork’s Editor-in-Chief • Vinyl Specialist • Spotify’s Former Data Guru • Hall of Fame Songwriter• John Legend Collaborator • Broadway Arranger • Indie Label Founder• Fender Exec

Recent Album a Day Themes: Trading Favorites • Concept Records • Peaked at 200 • Alliterative Artists • Hip-Hop Groups • Supergroups • Punk Ladies • Short and Sweet • Long Closers • This Year • Grammy Losers and Winners • Artists You Hate

Want more from Chris Dalla Riva? Get a copy of his book Uncharted Territory: What Numbers Tell Us about the Biggest Hit Songs and Ourselves wherever books are sold.