Key Takeaways

• The article argues Tupac Shakur’s plainspoken approach helped make him one of rap’s greatest lyricists.
• He could write intricate rhymes but often favored conversational storytelling over wordplay.
• His songs made personal stories of Black hardship resonate far beyond his community.

Tupac Shakur understood his own appeal long before he mastered it.

Speaking to Davey D in 1991, the then-20-year-old nodded to his Bay Area roots as inspiration for a stripped-down rap technique that would eventually help make him a legend. “Marin City was like a small town, so it taught me to be more straightforward with my style,” he explained. “Everything was straightforward. Poverty was straightforward. There was no way to say I’m poor but to say, ‘I’m po.’” Coming from a kid who was then more known for breaking a leg behind Digital Underground than verbal acrobatics, it could’ve sounded like an excuse for being mid. But it was actually a Trojan horse for rap transcendence. By trading dance moves for accessibility and intricacy for immediacy, Tupac dressed eternal truths in the language of the everyman and wrote his way to status as one of the greatest lyricists in American history. He didn’t evolve into a superstar in spite of his approach — he became one because of it.

Knowing that Tupac had bars means knowing his songwriting lineage — one that’s more the stuff of folk songs than rap folk heroes. As a pure technician, he peaked as a rapper who could twist and turn and backflip syllables through cross-coastal production. Tracks like “If I Die 2Nite” or “Me Against the World” prove he had a gift for alliteration and argumentative velocity. But he was ultimately more Bob Marley than Lupe Fiasco; more Dolly Parton than Lloyd Banks. Rather than dealing in flowery prose, quippy punchlines, or inscrutable metaphors, Tupac focused on legibility and visceral symbolism. He could be an elite cypher-dweller, but it’s more instructive to think of him as an old man with a porch, a bottle of gin, and a banjo to sing about his life of sin.

Framed in bluesy guitar and dedicated to his Black Panther mother, "Dear Mama" is an emotional bloodletting that’s as sentimental as it is unsparing, and Tupac’s bare-essential poetry structure mirrors the naked honesty of his confessional. Here, he juxtaposes painful hugs from a jail cell with the ephemeral bliss of a hot meal he usually knew not to expect. A hero falls only to be resurrected. “And even as a crack fiend, mama, you always was a Black queen, mama,” Tupac raps, elongating select vowels like a blues singer from Decatur, Georgia. If it’s simple phonetically, it’s labyrinthine symbolically: Somehow, Afeni Shakur’s fall from a symbol of regal Black triumph to drug-addicted destitution embodies the fraught destiny of Black America. And Tupac renders it all with the effortless, knife-edge precision of a ghetto nursery rhyme. They’re words a toddler could mumble. Even if the toddler doesn’t literally understand what he’s saying, Tupac’s elementary construction makes it so the toddler can feel it.

Tupac could shift between technical fireworks and everyday conversation

Imbued with kinetic rhythms and imagistic details, “Hail Mary” and his feature on Big L's “Deadly Combination” proved that Tupac could shimmy and Euro step his way to the hoop to score. Tracks like “Dear Mama” show he could also just take off to dunk from the three-point line. The approaches are different, but the distance covered is the same. Tupac makes another lengthy leap on “I Ain’t Mad At Cha,” an All Eyez on Me single that tightropes the past and present with traces of appreciation and bittersweet acceptance.

For this one, elaborate syllables, pretentious sermonizing, and sleek wordplay give way to a ghetto everyman’s humble reminiscence, with Tupac’s deliberate, one-sentence-at-a-time flow sounding like he’s reading a jail letter for his homies in the rec room: “We was once two n**gas of the same kind / Quick to holla at a hoochie with the same line.” He’s not talking at you. He’s talking to you. And depending on whether you’ve got an estranged best friend whose sister you wanted to smash — but had the wherewithal not to — and how many after-school fights you got into, he might be talking through you.

Where Tupac ranks among the best lyricists

When Pac wasn’t eviscerating tracks in a classical fashion, he was building worlds by channeling universes that already existed. Through unpretentious, monosyllabic rhyme structures and blunt phrasing that punctuated even his best technical displays, Tupac could erase the gaps between one adjacent existence and another with frank, bleary-eyed sincerity (“Old School”) or fatalistic exasperation (Thug Life's “Under Pressure”). Bars like “I wonder if the lord still cares for us n**gas on welfare” (“My Block”) could be uttered by Tre or Doughboy, Latasha Harlins or Eric Garner, maybe your grandma. In one way or another, maybe everyone. Tupac’s weathered block-boy vignettes turned episodes of Black plight into global proverbs, stories that are true everywhere from Marin City to Morocco.

Of course, the absolute best lyricists blend Tupac’s emotional digestibility with Shakespearean metaphors and Simone Biles agility. Pac mastered the first part, but was merely excellent in the second. Eminem’s “Rock Bottom” and “Cleaning Out My Closet” channel the same manic exasperation of the best Tupac songs — just with tighter syntactic precision. Yasiin Bey sounds like an intelligent brother from ‘round the way on most of his songs. It’s just that his ideas are so grand, he uses appropriately grand phrasing to capture them. But it’s no less effective. As a sentence writer, Tupac might not match their lyrical heights, but not being the absolute best doesn’t mean you aren’t one of them — just ask the rap Michael Jordan.

Like the rap Avatar he also is, JAY-Z has long since mastered every aspect of rap songwriting, combining gut feelings with lucid introspection and premier rhyme economy. So HOV’s in a unique position to appreciate Tupac’s understated songwriting greatness.

“I think that was one of Tupac's superpowers. He was able to say really simple things, really powerful things,” HOV said in Episode 3 of JAY-Z In 8. “[On ‘Dear Mama’] he struck a real emotional chord. Like, he took a piece of you and brought it to the forefront.”

Many read JAY-Z’s quote as a sneak-diss to a former rival. But it’s actually words of praise from one master to another — the ultimate “Game recognize game.” It’s also a nod to a camouflaged songwriting craft. Tupac’s simplicity wasn’t the absence of technique; it was a technique itself. People cite Pac’s folksy rhyme approach as proof of his technical limitations. But the truth is, he was unlimited because he knew the best songs aren’t always technical.