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Home · Black Music Month

Black Music Month: Guess The Old-School Rappers

Let's go back, way back to a time when hip hop was the only thing blasting in your speakers. In honor of Black Music Month, we're testing your hip hop IQ. Think you know everything about your favorite old-school rapper? From their lyrics to their top hits? Put your knowledge to the test and match these iconic faces to their work.
By Yolanda Sangweni · Updated October 28, 2020
01
Rapper’s Delight

This all-girl trio were behind the 80s rap hits like “Express Yourself” and “Tramp.”

Memorable lyrics: “C’mon girls, let’s go show the guys that we know/ How to become number one in a hot party show.”

Black Music Month: Guess The Old-School Rappers
Michael Ochs Archive/ Getty
02
Rapper’s Delight

Yup, you guessed right! We’re talking about Salt-n-Pepa, long considered one of the best female rap groups of all time.

Black Music Month: Guess The Old-School Rappers
Michael Ochs Archives/ Getty
03
Rapper’s Delight

Though she made her mark in the South, rapper Shawntae Harris was raised in Chicago. She chose her stage name because she was a “spoiled only child.”

Memorable lyrics: “Them calls me the funkdafied, funkalistic, vocalistic.”

Black Music Month: Guess The Old-School Rappers
04
Rapper’s Delight

With songs like “Funkdafied” and “Give it 2 You,” Da Brat was a bonafide hip hop hitmaker in the early 90s.

Black Music Month: Guess The Old-School Rappers
05
Rapper’s Delight

His dapper style and impeccable dance moves earned this Brooklyn emcee respect from the fellas and lots of love from the ladies.

Memorable lyrics: “I’m the authentic poet to get lyrical/ For you to beat me, it’s gonna take a miracle/ And, stepping to me, yo that’s the wrong move.”

Black Music Month: Guess The Old-School Rappers
Al Pereira/Getty
06
Rapper’s Delight

Big Daddy Kane is still going strong. Catch him at the ESSENCE Fest on July 6.

Black Music Month: Guess The Old-School Rappers
Al Pereira/Getty
07
Rapper’s Delight

This Harlem rapper, also known as the Human Beat Box, got his start as part of the Get Fresh Crew.

Memorable lyrics: “Have you ever seen a show with fellas on the mic/ With one minute rhymes that don’t come out right/ They bite, they never right, that’s not polite.”

Black Music Month: Guess The Old-School Rappers
Getty
08
Rapper’s Delight

Doug E. Fresh has barely slowed down since making his debut in the 80s. Catch him at the ESSENCE Fest on Thursday, July 4.

Black Music Month: Guess The Old-School Rappers
09
Rapper’s Delight

Afrocentric and ready to challenge any stereotypes about women, this New Jersey native was the epitome of girl power hip hop.

Memorable lyrics: “A woman can bear you, break you, take you/ Now it’s time to rhyme, can you relate to/ A sister dope enough to make you holler and scream.”

Black Music Month: Guess The Old-School Rappers
Getty
10
Rapper’s Delight

Though she’s stepped away from rapping, the Queen (Latifah) is still commanding crowds on the big and small screen.

Black Music Month: Guess The Old-School Rappers
Getty
11
Rapper’s Delight

This Compton native’s music always celebrated female empowerment and addressed sexism in the music business.

Memorable lyrics: “I’m in the 90s, you still in the 80s, right/ I rock the mic, they say I’m not lady-like.”

Black Music Month: Guess The Old-School Rappers
Getty
12
Rapper’s Delight

You can’t play with my Yo-Yo (Yolanda Whitaker)! The veteran rapper will be part of the ensemble cast of BET’s reality show Hip Hop Sisters, set to debut this fall.

Black Music Month: Guess The Old-School Rappers
Getty
13
Rapper’s Delight

These New Yorkers’ debut album The Message (1982) brought a new wave of rap with social commentary. And who could forget their incredible style?

Memorable lyrics: “Don’t push me cause I’m close to the edge/ I’m trying not to lose my head.”

Black Music Month: Guess The Old-School Rappers
Getty
14
Rapper’s Delight

Grandmaster Flash and the Furious Five is one of the most respected and influential hip hop groups of all time.

Black Music Month: Guess The Old-School Rappers
15
Rapper’s Delight

This California native left a successful hip hop group behind to pursue a solo career. In 1992 he starred in the critically-acclaimed film Boyz n the Hood.

Memorable lyrics: “Just waking up in the morning, gotta thank God/ I don’t know but today seems kinda odd/ No barking from the dog, no smog.”

Black Music Month: Guess The Old-School Rappers
Al Pereira/Getty
16
Rapper’s Delight

Two decades after his debut, Ice Cube is still going strong as a rapper, actor and screenwriter.

Black Music Month: Guess The Old-School Rappers
Al Pereira/Getty
17
Rapper’s Delight

This Bronx rapper, whose stage name stood for “Knowledge Reigns Supreme Over Nearly Everyone,” rose to fame with hits like “The Bridge Is Over” and “South Bronx.”

Memorable lyrics: “So you think that hip-hop had its start out in Queensbridge/ If you pop that junk up in the Bronx you might not live.”

Black Music Month: Guess The Old-School Rappers
Ebet Roberts/ Getty
18
Rapper’s Delight

You guessed right: We’re talking about the one and only KRS-One.

Black Music Month: Guess The Old-School Rappers
Ebet Roberts/ Getty
19
Rapper’s Delight

This British-born rapper with a penchant for big gold chains and diamond jewelry is known for songs like “Teenage Love” and “Hey Young World.”

Memorable lyrics: “Hey Mr. Bigshot/ hey, don’t you look fly?/ But you don’t have a nickle… ohhhh, my my my/ You’ve been fightin again and, you forgot why.”

Black Music Month: Guess The Old-School Rappers
Al Pereira/Getty
20
Rapper’s Delight

We’re talking about Slick Rick, aka Rick the Ruler.

Black Music Month: Guess The Old-School Rappers
Al Pereira/Getty
21
Rapper’s Delight

Best known for songs like “Tennessee” and “Mr. Wendal,” this Southern collective brought alternative hip hop to the forefront.

Memorable lyrics: “My day was going great and my soul was at ease/ Until a group of brothers started bugging out.”

Black Music Month: Guess The Old-School Rappers
22
Rapper’s Delight

You guessed right! Arrested Development, led by Speech (pictured), continues to make music and recently released their 10th studio album, Standing at the Crossroads.

Black Music Month: Guess The Old-School Rappers
Getty
23
Rapper’s Delight

This Cleveland collective, known for their melodic style of rhyming, was signed by N.W.A.’s Eazy E.

Memorable lyrics: “And I’m gonna miss everybody/ I done rolled and blows my gauge/ Looked at him while he lay/ When playing with destiny, play too deep for me to say.”

Black Music Month: Guess The Old-School Rappers
Getty
24
Rapper’s Delight

We’re talking about Bone Thugs n Harmony.

Black Music Month: Guess The Old-School Rappers
Getty
25
Rapper’s Delight

This Oakland alternative hip hop group is behind 90s hits like “Doowutchyalike” and “The Humpty Dance.”

Memorable lyrics: “I’m crazy, allow me to amaze thee/ They say I’m ugly but it just don’t faze me/ I’m still getting in the girls’ pants/ And I even got my own dance”

Black Music Month: Guess The Old-School Rappers
Getty
26
Rapper’s Delight

You guessed it: Digital Underground.

Black Music Month: Guess The Old-School Rappers
Getty
27
Rapper’s Delight

This Queens-bred rapper is known for his rapid-fire lyrical style and, um, amazing lips. 

Memorable lyrics: “When I’m alone in my room sometimes I stare at the wall/ And in the back of my mind I hear my conscience call.”

Black Music Month: Guess The Old-School Rappers
Getty
28
Rapper’s Delight

He rhymes like no other. Catch LL Cool J at the ESSENCE Fest on Friday, July 5.

Black Music Month: Guess The Old-School Rappers
Getty
29
Rapper’s Delight

This California crew of rappers and producers were among the first to be labeled as “gangsta rap.” Their controversial name (Hint: it rhymes with triggers) coupled with their risque subject matter didn’t gain them many fans over 30, that’s for sure.

Memorable lyrics: “Runnin’ with my brothers, headed for the homebase/ With a steady pace on the face that just we raced.”

Black Music Month: Guess The Old-School Rappers
Jeff Kravitz/ Getty
30
Rapper’s Delight

That’s right, we’re talking about N.W.A. (N***az With Attitude).

Black Music Month: Guess The Old-School Rappers
Jeff Kravitz/ Getty
31
Rapper’s Delight

This Grammy Award-winning New Jersey trio made their debut in 1989 with the release of Independent Leaders. Their most succesful song sampled the Jackson 5’s “ABC.” Their second-biggest hit sampled Bob Marley’s “No Woman, No Cry” and featured the lyrics “If you ain’t ever been to the ghetto/ Don’t ever come to the ghetto/’Cause you wouldn’t understand the ghetto.”


Black Music Month: Guess The Old-School Rappers
32
Rapper’s Delight

Remember Naughty by Nature?


Black Music Month: Guess The Old-School Rappers
Getty Images
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