13 Dec,2023
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Some may scoff at this placement on the list, but Lil Wayne is deserving. Ignore his silly auto-tuned sing-song rapping in his radio-centric singles and you’ll find a truly skilled lyricist. For decades now he’s honed his craft to include multisyllabic rhyming, clever rhyme schemes, and gobs of wordplay.
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Sage Francis comes from the intellectual “backpacker” school of rap, which packs more value into each song than any other sub-genre of hip hop. Francis can do it all as good as any other artist, but his real strength is his storytelling and imagery.
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Many of the best rappers of all time call Kool G Rap one of their own favorites. He was an early adopter of multisyllabic rhyming while maintaining that smooth New York flow that inspired several others on this list. While G Rap never hit mass popularity due to his mafioso style of lyrics, anyone who knows rap knows he’s a top rhymer.
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Kendrick has a lot going for him. His voice, his flow, and his lyrical content fit so perfectly with the jazz-inspired instrumentals on his first three albums. He’s showing that he can grow and evolve over his discography now, too.2
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Tupac Shakur (or 2Pac or Makaveli) spent his teenage years writing poetry and rapping. But, based on the quality of his debut album, 1991’s 2Pacalypse Now, the effort was well worth it. Three more studio efforts would follow before his untimely demise in 1996.
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Nas has all of the skills of anyone else on this list but likes to be less strict with the rules of technical rhyming. This looseness allows him to have far more involved lyrical content. He bridges the gap between annoyingly preachy and casual, where you actually learn things by listening.
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You know how I’ve complained above about rappers who try to get complex and their lyrics suffer? Not Chali 2na. He does not waste an opportunity to place an internal or external rhyme with multisyllables, and his lyrics make perfect sense and are mature.
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Tech N9ne has the best flow of all time, hands down, zero questions. His use of triplets, sixlets, complex rhyme schemes, multisyllabic rhyming, weird time signatures, and more put him almost at the top.
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Like Nas, Jay-Z is a rapper who’s capable of being complex but chooses to be more loose with his style. This gives him more room to hone and share his message, which is his true strength.
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If you ask me, Eminem is getting worse with time as he “evolved” through shock rap to sing-song rap to trying to sound like the modern mumble rappers. But if you’ve explored his discography, especially his earliest work and his freestyles, it’s unquestionable.
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