Here Are The Nine Best Rap Songs To Introduce A Newcomer To Hip-Hop

Hip-hop is the most popular genre of music in the world. With that being said, there are still, incredibly, a great number of people who are not familiar with the genre, its players, its rules, its, canon, its milieu, and its profound effects on its listeners, even forty years after its inception.

Maybe they have misconceptions or preconceived biases due to its negative portrayals in mainstream media, or perhaps they feel that they won’t find anything to relate to in it, due to its reputation for fierce, rugged content centered on poverty and social injustice or for vulgarity and profanity that may turn off more sensitive listeners. Some think that they won’t find anything musically worthy, since many rappers — but not all — don’t play any instruments. So, how do we introduce hip-hop to neophytes who might be curious, or change the minds of detractors who’ve so far refused to give it a chance? Here are nine songs — by no means a comprehensive or complete list, but a reasonable primer — that might persuade a reticent first-time listener into in an enthusiastic long-term fan. Feel free to add on in those comments.

Eric B. & Rakim, “Paid In Full”

When Rakim says, “Thinking of a master plan,” to set off this masterful, one-verse record, it is simultaneously one of the most complete statements of what rap and hip-hop represent, and one hell of a cliffhanger, leaving the listener almost desperate to hear what comes next. A song as much about the craft and process of writing rap (“A pen and a paper, a stereo, a tape of / Me and Eric B and a nice big plate of / Fish, which is my favorite dish”) as it is a rapper’s manifesto (“So I start my mission, leave my residence / Thinking how could I get some dead presidents”), “Paid In Full” is among the first rap songs to truly indicate the potential complexity in the nascent art form, while remaining a major building block in what rap was to become. Any MC who flexes multisyllabic, interior rhymes should be paying royalties to Rakim the God for showing what rap could be in 1987.

The Notorious B.I.G., “Ten Crack Commandments”

When it comes to concept tracks, rap does it as well as any other genre. Pharaohe Monch imagines himself as a bullet on “When The Gun Draws,” Nas embodies the gun itself on “I Gave You Power.” Nas, Lupe Fiasco, and Jidenna have all wondered at a topsy-turvy world where Black folks and Anglos switch social class, and rap space opera is an actual thing that exists and is good. But when it comes to rhyme or prose, nothing beats a good list. Biggie Smalls understood that twenty years ago, penning a manual of rules for any listener interested in surviving the drug game that sounds as smooth and informative today as it did upon release. Fans still quote the Commandments at any number of provocations, whether watching the latest episode of Snowfall and Power, or repurposing the rules for every other profession from athletes to middle management. The longevity of the “Ten Crack Commandments” reveals just how deeply rappers can make fans relate to their content, even if they have no personal experience with the subjects being addressed.

U.G.K. featuring Outkast, “International Players Anthem”

There are four verses on this song, and all of them approach rap a different way, yet somehow all are exemplary of Southern rap as a subgenre. There is Andre’s soul-searching, almost-spoken word lead off, followed by Bun B and Pimp C’s far less soul-searching pimp talk, bookended by Big Boi’s words of wisdom with regards to baby mamas and making good choices. There are gems throughout; “Keep your heart, Three Stacks,” “Never f*ck without a rubber,” “We rockin’ Russian sable, keep that ‘chilla on the rack,” and “Better choose the right one or pick the kiddies up,” are nuggets of truth we should all aspire to live by. However, the true star of the track is that 808-ridden, soul-drenched Willie Hutch sample, that no one can resist singing along to, on-key or off. It’s the definition of what makes Southern rap so distinct and fun.

Jay-Z, “Allure”

To be honest, there are any number of Jay-Z songs that you could play for a hip-hop newcomer — heck, you could just run Reasonable Doubt straight through, and most people could instantly grasp the breadth and depth of much of what rap is. But nothing on Reasonable reaches out grabs the listener like “Allure” from Jay’s The Black Album. On “Regrets,” he tells you that he has, well, regrets — it’s right there in the title. But “Allure” takes it to another level, illustrating them through the depiction of a hustler detailing the hows and the whys and the unfortunate collateral damage of chasing the adrenaline rush of fast money: “All the Christies in every city and Tiffany Lanes.” Pharrell’s mournful strings and keys just add another dimension, a master class in how the production in rap can set a mood as well as the verbal imagery, when it’s allowed to.

Nas featuring Lauryn Hill, “If I Ruled The World”

Nas purists will tell you his best songs are “Life’s A B*tch,” or “N.Y. State Of Mind,” or “It Ain’t Hard To Tell,” from his seminal debut Illmatic. They illustrate his early fatalism, they vividly paint a picture of hard times at the bottom, with incredible wordplay and mastery of cadence thrown in. But what if I told you that Nas is at his best when he is optimistic? “If I Ruled The World” is Nas at his most transparent, finally allowing himself to hope for all the things that were beyond his imagining on his debut. It perfectly sums up hip-hop’s aspirational nature, but scratch the surface and you can hear what goes into that nature. He conveys the sense that something has been systematically denied poor black people in America for centuries with just one line: “You could be poor or rich, still nobody want a n*gga have a sh*t!” If the net result will be same either way, why not be rich?

The Fresh Prince & DJ Jazzy Jeff, “Parents Just Don’t Understand”

Don’t look at me like that. I know what I’m talking about here. While some may point to Slick Rick’s “Children’s Story” or Common’s “I Used To Love H.E.R.” as the pinnacles of storytelling rap tracks, “Parents Just Don’t Understand” is something else altogether. It doesn’t have the premature cynicism of either of the aforementioned, but it is every bit as clever, with twists and turns in the plot’s narrative. Beyond that, it’s relatable, funny, witty, and illustrates the lighthearted side of rap, breaking the stereotypical image of mean-mugging street youth relating tales of drugs and violence or salty hip-hop heads complaining about how rap was better “back in the day.” Also, the video — a typically low budget ‘80s affair — is hilarious and laid the aesthetic blueprint for Will Smith’s iconic Fresh Prince Of Bel Air theme.

Heavy D & The Boyz featuring Kool G Rap, Grand Puba, C.L. Smooth, Big Daddy Kane, Pete Rock, and Q-Tip, “Don’t Curse”

Ah, the posse cut. The staple of rap of one-upmanship, standing proudly alongside the rap battle as a watermark for hip-hop’s focus on competition. While “The Symphony” was one of the earliest, and later entries into the canon may have demonstrated more virtuoso examples of wordplay and technique, “Don’t Curse” incorporates a very simple gimmick and then asks its respective players to execute — which they all do, flawlessly. As Kool G Rap, Big Daddy Kane, Grand Puba, Q-Tip, Pete Rock, and C.L. Smooth wind around and through sinuous, circular flows, they come close, cleverly dancing around the taboo lingo in slick ways, proving that rap needn’t be vulgar to sound hard.

Missy Elliott, Work It

Twenty years after the release of Supa Dupa Fly, it seems Missy Elliott is only just getting her due as an MC and songwriter. She has often been overlooked as a top tier rapper because she doesn’t follow all the rules, but that’s the rub: The only way to break the rules of rap and still sound as good as Missy does on tracks like “Work It” is to have mastered them better than anyone else ever has, so she knows exactly which ones to break and how. And does she ever break them. She leaves the English language at the door several times, she reverses entire bars, and she expresses black female empowerment, which is often in short supply in a male-dominated genre that most readily imitates the pimp-flavored Blaxploitation movies of its authors’ youth. Missy shows how rap can be twisted and repurposed in unconventional, unusual ways while still meeting the criteria of making fun, funky hip-hop sound totally unique.

Mos Def & Talib Kweli featuring Common, “Respiration”

This one’s kind of a cheat; it’s got Mos Def, one of the smoothest rappers of the ’90s, Talib Kweli, one of the densest, and Common, one of the most poetic. Basically, anyone who is a fan of J. Cole, Kendrick Lamar, Isaiah Rashad, Joey Badass, Lupe Fiasco, or Chance the Rapper in 2017 owes a debt of gratitude to Mos Def & Talib Kweli Are Black Star, because their DNA runs all through modern, densely structured hip-hop. From the closely-knit rhyme patterns to the poignant, poetic imagery, Black Starpractically created and defined the “conscious rap/backpack rap” sub-genre, including laying the foundation of the proudly independent marketing plans of today. They exemplified artist ownership at a time when the only way most artists could even sniff at radio play was to sign to a major and give up ninety percent of their publishing, creating a lane that didn’t exist and making it possible for future generations to take full advantage of tools like streaming and social media to monetize their own art without compromising for the benefit of a faceless, corporate monolith. Without Black Star, there would be no Chance, no Kendrick, and no Drake — from lyrics to business plan, they taught an entire generation how to rap for fun and profit.

Kanye West, “Stronger”

If Missy broke the rules of rap in 2007, Kanye West grabbed the rulebook, ripped out half the pages, scribbled in crayon on the other half, set the book on fire, then threw it out the window. Previous to “Stronger,” the (mis-)conception of EDM among most rap heads was that it was for weird white people at raves, tripping on ecstasy and waving glow sticks around in laser lit, abandoned warehouses. West leaned hard into that aesthetic with the groundbreaking first single from Graduation, a wild departure from his earlier soul samples and Dr. Dre drums. He claims to have gone through over a dozen iterations of the mix to the beat, obsessing over the smallest details; the hard work paid off, as “Stronger” succeeding in taking hip-hop and rap into new realms (or reimagining the earlier electro styles that had been lost to antiquity post-Run DMC). Any new listener with a preconceived notion of rap as bass and drums would be blown away to find that it works just as well with a noisy, robotic Daft Punk sample and an anime-inspired music video that is every bit as braggadocious as 50 Cent pitching nicks on a darkened street corner in the projects.