Formation | Community | Culture

Hip Hop History: 1991-2003

“I’ve been accused of not liking hip hop and that’s just not true. I got a little 50 in my iPod. I really do. I like ‘In Da Club.’
Have you heard the beat to ‘In Da Club’? Love that.”
– Oprah Winfrey, in an interview with MTV (2006)


Everyone loves rap. Even people that say they don’t like rap like rap. Oprah Winfrey was the most outspoken critic of rap in the past 20 years, and she has 50 Cent on her iPod. Even the Pope likes to free style every now and then.


Pope Francis, definitely not rapping. (Photo cred: TIME)

When in Rome, am-I-right? The thing about hip hop is that it spans cultures, it brings people together, it unites a number of musical influences and styles into a dope beat and keeps their heads ringin’, as the good Doctor once put it.

So, let’s start our third (of six? Or five? Seven if I take an extra week off before Christmas?!) installment in this inimitable Hip Hop History. Last week, we spent 2,000 words on Tupac, Biggie, and Tupac-vs-Biggie, because that’s what they deserve.

But they weren’t the only ones on the Scene in Rap’s Golden Age (1991-97). In this episode, I’m going to highlight some of those other elite rappers/groups from ’91-97 and take us all the way up to the current state of affairs. That’s right, haters, we’ve got more than two decades of dope beats to cover, and I’m going to do it in just 1500 words or … well, or maybe more. We’ll see.

But let’s start with a little pop quiz.

Who do you think has sold the most albums of all time? Rank the following artists/groups (listed alphabetically) by total album sales one through ten.

50 Cent
The Beastie Boys
Dr. Dre
Kanye West
MC Hammer
Notorious BIG
Tupac Shakur

Who do you think comes out on top? Top five? The answers will be provided in just a bit. (Because that’s how my publicist tells me I keep readers through these overly long-winded essays.)

Let’s get to my favorite hip hop artists of the last two and a half decades!!!


A Tribe Called Quest  

Rap is not pop, if you call it that then stop.
– A Tribe Called Quest, “Check the Rhime” (1991)

Now, the first group that, IMHO, kicked off rap’s Golden Age, transformed hip hop, and were among the most innovate musicians of our generation: A Tribe Called Quest. I mentioned them as a descendent of the Bambaataa / Zulu Nation (ca. 1982 onward) family tree, but Quest was just a flat-out wonderful thing for hip hop.



A Tribe Called Quest, circa 1991. (Photo cred: Power 106)

Tribe’s niche of hip hop history is significant; I don’t know what it’s called in actual music histories, but I’ll call it “deep hip hop” in addition to the aforementioned “mostly positive street rap” label. What I mean is that Tribe found depth in both its beats and its lyrics. They were truly creative in creating a new rhythm and flow for hip hop, blending African and American styles, while also layering often profound lyrics (in addition to the early “Can I Kick It?” simplicities). They had a good bit to say, and they said it really well.

Okay, if knowledge is the key then just show me the lock.
Got the scrawny legs but I move just like Lou Brock,
With speed. I’m agile plus I’m worth your while.
One hundred percent intelligent black child.
– Tribe, “Check the Rhime”

The Queens-based group—including great rap names like Q-Tip, Phife Dawg aka Phife Diggy aka Malik Taylor—has been called the most intelligent and artist rappers in history, and their refined, thoughtful influence can be heard in the lyrics of Nas (more on his artistic bent in a moment), The Roots, and Kanye West.

If you’re a hip hop fan, you need to do yourself a solid and pick up A Tribe Called Quest’s The Low End Theory (1991), Midnight Mauraders (1993), and Beats, Rhymes and Life (1996) asap.

[Side Note #14: Tribe members Q-Tip, Phife, and Ali were just 19 when they first recorded “Can I Kick It?” and only 28 when they disbanded in 1998. Oh the records that could have been.]

The Roots

Yo, we obviously need to tone it down a bit
Running round town spending time like it’s counterfeit
Everybody catching hay fever like sinuses
Step in my arena let me show y’all who the highness is
You might say I could be doing something positive
Humbled head down low and broke like promises
Soaking and broken in a joke like comics is
Not enough paper to be paying folks compliments
But when that paper got low so did my tolerance
And it ain’t no truth in a dare without the consequence
Listen if it not for these hood inventions
I’d just be another kid from the block with no intentions
On the dock of that bay serving a life sentence
Even if I’m going to hell I’m gonna make an entrance.
– The Roots, “The OtherSide” (2011)

We’ve made it to another one of my all-time favorites: The Legendary Roots Crew.


The Roots, 2015, for The Tonight Show. (Photo cred: Mark Seliger/NBC)

Questlove, Black Thought, and the gang just make gorgeous music, number one, and number two, they genuinely have a message to convey. The Roots formed in Baltimore in 1987, mostly doing local acts and going by the names “Black to the Future” and “The Square Roots” before their first full-length album in 1993 as, simply, The Roots. But just try and tell me you don’t love the name “Black to the Future” as the name for a rap group.

Their style is almost completely unique: they work a full band, blend soul beats with jazz and rap, and their lead guy is a drummer. Their lyrics and acts have provided commentary on a number of issues—from inner city public education to contemporary politics. If there is a smarter, more attentive rap group in the world today, I haven’t found them.

[Side Note #15: Things Fall Apart takes its title from a line from a W.B. Yeats poem, making it presumably the first and only rap album titled in reference to a W.B. Yeats poem.]

Their beats on Do You Want More?!!!??! (1994), Things Fall Apart (1999), The Tipping Point (2004), Game Theory (2006), How I Got Over (2010), and Undun (2011)—wait and Phrenology (2002)—are some of the best in history. These are albums you want. (Yes, I know that’s like eight albums.) In total, The Roots have released 13 studio albums, and dopely, each features continuous track numbering—so their second album begins with track 18, and their most recent album’s tracks are numbered 171-181. One day I hope to do something—anything—that cool. Also, I’d like to keep a comb in my hair like Questlove.

If you are new to The Roots and just want to pick up a couple songs to sample their style, I recommend:

“Don’t Feel Right”
“Dear God 2.0”
“The OtherSide”
“The Seed (2.0)”

Let me also say in closing on The Roots that Jimmy Fallon’s inclusion of them as his house band on Late Night was one of the great decisions of the past ten years. As Pharrell Williams put it in his appearance with The Tonight Show this year (Fallon brought The Roots with him), the decision was one more step in solidifying hip hop’s place in American culture and music history—it was no less than NBC’s affirmation of the hip hop community as having a central place in our lives today. Don’t miss The Roots on Barack Obama Slow Jams the News and if you have you have any question whether these guys are talented, question no more. It’s a good thing people as talented as The Roots don’t have to take themselves too seriously.


Now throw your hands in the air
And wave ‘em like ya just don’t care
And if you like fish and grits
And all the pimp [expletive]
Everybody like me hear ya say
“Oh yea-err”
– OutKast, “ATLiens” (1996)

I could have organized this particular essay as “Regional Rap,” identifying major rappers and their hometowns as a way of conveying their particular styles and contributions. Having already looked at NYC (Notorious BIG, Puff Daddy, and Jay-Z) and LA (NWA, Pac, Dre, and Snoop Dogg), we’d look at the “other” / regional rap centers: Baltimore/Philly (Tribe, The Roots), Chicago (Common, Kanye West), Detroit (Eminem) and so on. And we would still most certainly hit Atlanta, aka the Dirty South, aka the Dirtaae Dirteee, which would include Geto Boys, Ludacris, Lil John (YEAAAAH!!!), T.I., Young Jeezy, and, most notably, OutKast.


OutKast, circa 1994. Andre 3000, left, with Big Boi, right. Also pictured, an early 90’s Cadillac, I think. (Photo cred: National Public Radio)

[Side Note #16: This doesn’t include other Dirty South offshoots in Miami (Rick Ross the Big Boss, Trick Daddy), New Orleans (Lil’ Wayne, Juvenile), and Bowling Green, Kentucky (Nappy Roots).]

[Side Note #17: Atlanta also produced Lecrae, whose 2014 album Anomaly was perhaps the best of the year by any standard and will be covered in another essay, probably.]

[Side Note #18: If you’re wondering if there are any rappers in the Guinness Book of World Records, there are quite a few. For example, Twista is the fastest rapper in history, having been recorded at 11.2 syllables per second in 1992, and Chiddy (a Dirty South B-list rapper) holds the record for longest freestyle rap in history, at 9 hours, 18 minutes, 22 seconds, but the record is held under some controversy, because, again, only residents of East Point ATL have ever heard of Chiddy.]

OutKast blended traditional hip hop beats with funk, soul, gospel, jazz, some Carribean flavor, and adopted much of the Dirty South’s simultaneous influences, including Crunk (Lil’ John and Co.). Rappers Andre ‘3000’ Benjamin and Antawn ‘Big Boi’ Patton are some of the all-time greats, and they won six Grammys in just six studio albums: Southernplayalisticadillacmuzik (1994), ATLiens (1996), Aquemini (1998), Stankonia (2000), Speakerboxxx/The Love Below (2003), and Idlewild (2006) before disbanding that year. Their jams “Rosa Parks,” “B.O.B. (Bombs Over Baghdad),” “Ms. Jackson,” “The Whole World,” and “Hey Ya!” are some of the most widely recognized rap songs of the past 15 years.

[Side Note #19: One of these just-mentioned tracks makes my forthcoming Top Ten Rap Songs of All Time list. Oh man, I can feel the controversy coming. It’s a good thing I don’t have many readers.]

50 Cent

“People love the bad guy. I watch movies all the time and root for the bad guy and turn it off before it ends because the bad guy dies. It’s cinematic law: the bad guy has to die.
But sometimes the bad guy gets a record deal and becomes a superstar like 50.”
– 50 Cent, interview with The Guardian (2003)

If you were going to create a rapper from scratch, like in some sort of lab or something, you would end up with 50 Cent.

50 cent

Curtis James Jackson III, aka 50 Cent, center, with two friends and what’s presumably a bottle of high-end olive oil. (Photo cred: the Internet)


As Shea Serrano notes, just look at 50 Cent’s life before breaking through—it’s basically everything you need to appeal to all rap fans as quote unquote “legit.”

– Underprivileged youth who never knew his father (check)
– Mother was a drug dealer, murdered when he was young (check)
– Became a drug dealer himself at 12 (check)
– Arrested many times as a child, dropped out of school (check)
– Shot nine times, including once in the face, in an attempted assassination (check)
– Did not die (check)
– Deemed a risk and dropped by a major record label (check)
– Picked back up off the street by the biggest rap producer of all time (checkmate)

You couldn’t sit around all day and come up with a better hip hop curriculum vitae. Does it make for a great life? It’s hard to say. But it definitely doesn’t make you “soft,” which is the opposite of “legit.”

50 (pronounced: “Fitty”) Cent aka G-Unit aka Curtis James Jackson III is a bit of an oddity. With every other rapper and group in this History, I get the sense the individual would have broken through in one way or another even if it wasn’t for one big break. But with 50, I’m not so sure. If Eminem hadn’t stumbled upon his mix tape (so the legend goes) and if he hadn’t sent it to Dr. Dre, where is Mr. Jackson the Third now? Sure, his “In Da Club” is one of the freshest beats ever made—it’s vintage Dre meets G-Unit memoir.

If I could compare 50 to anyone outside the rap world, I’d choose Jerry Seinfeld. Both had an unexpected rise to national stardom—Seinfeld is the most successful TV comedy in history, and 50’s 2003 album Get Rich or Die Tryin’ is one of the top ten bestselling rap albums ever—and realized they never had to do any real work again, so they just spent the next few decades chilling, collecting royalty checks, and doing odd jobs here and there (see: “Comedians in Cars Getting Coffee,” which opens every episode with “Hi, I’m Jerry Seinfeld!” and 50’s foray into entrepreneurship projects including Vitamin Water and a boxing company) just to remind people that he’s still famous for that one thing he did back then that we still love.

[Side Note #19: 50 declared bankruptcy about four months ago.]

Quiz Answer Key

If you guessed the most popular rappers in history in this particular order, you my friend, are one big winner.

Eminem (155 million total album sales)
Kanye West (121m)
Jay-Z (100m)
Tupac Shakur (75m)
The Beastie Boys (50m)
MC Hammer (50m)
50 Cent (30m)
OutKast (25m)
Notorious BIG (17m)
Dr. Dre (13m)

This isn’t a definitive top ten list of course, but it’s representative of the fact that the best rappers are not proportionately rip of album sales. (It should be noted that these figures only include Dr. Dre’s two personal studio albums The Chronic and 2001, not his many compilations and production efforts.) Yes, we live in a world where 50 Cent could have one great song (“In Da Club,” 2003) and do more in career sales than Notorious B.I.G. And we live in a world where The Beastie Boys and MC Hammer exist. Things are unfortunate.

We’re running out of time, and I want to leave plenty of time for the five best and most important rappers since Pac and Biggie in Part Four: Jay-Z, Dr. Dre, Snoop Dogg, Eminem, and Kanye West.

See you next time, haters.

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