1 Eminem
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 heard his discography, especially his earliest work and his freestyles, it's unquestionable... he holds the crown.
Eminem has taken mastery to another level. When he's not worried about mass appeal, his music is next-level in terms of complexity, vocabulary, rhyming phrases you'd never think to put together, etc. His freestyle skills are truly limitless, to the point where he's doing things that seem inhuman.
He played the main character in the drama film 8 Mile, based around rap battles. He's won 15 Grammys, 8 American Music Awards, and 17 Billboard Music Awards, among many others. He's had 10 number one albums on the Billboard 200, all debuting at #1. He's the only artist to have achieved this.
2 Tech N9ne
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 puts him almost at the top. His energy is unmatched. So why isn't he number one?
Because he refuses to break out of his complexity. He follows the rules so hard that sometimes he even makes up words or phrases to fit into the multi. It's not a big deal but if he can get past that and perhaps enhance his storytelling, he can easily take the top spot.
He's a co-founder of Strange Music. His music has been featured in film, TV, and video games. He's continued to remain independent instead of signing to a major label, and while that's slowed him down a bit he's still finding mainstream success without them.
3 Chali 2na
You know how I've complained above about rappers who try to get complex and their lyrics suffer? Not Chali 2na. He manages to not waste a single chance to place an internal or external rhyme with multisyllables, and his lyrics make perfect sense and are mature. His baritone voice is so pleasant too.
Chali 2na is what mastery sounds like. There's nowhere to improve. The only problem is he chooses to make more uplifting songs (which can get old) and attempts to make pop hits. It's one of my same problems with Big Pun, chasing money with cheesy pop songs. Regardless, Chali is at the top of the rap game in terms of refinement.
He's a member of both Jurassic 5 and Ozomatli. His stage name comes from the deep-voiced animated mascot for StarKist Tuna. He's known in the rap world but many were introduced to him from a collaboration with Linkin Park.
4 Jay-Z
Like Nas, Jay-Z is a rapper who's extremely capable of being overly-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. When you listen to Jay-Z, you hear a guy who's experienced in life and has a lot of mature things to say.
Everyone loves it, which is why he's the wealthiest American musician and the first rap billionaire. He's in the Songwriters Hall of Fame, has 22 Grammy Awards, and has sold over 50 million albums and 75 million singles. You've heard of Jay-Z and heard his music, what more is there to say.
Jay-Z founded Roc-A-Fella Records and the clothing retailer Rocawear. He founded and owns a luxury sports bar chain called 40/40 Club. He bought the streaming service Tidal recently. Perhaps most impressive, he's married to the famous singer Beyonce.
5 Sage Francis
Sage Francis comes from the intellectual "backpacker" school of rap, destined to never be mainstream but provides more value packed 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 story telling and imagery.
Francis could easily be listed even further up the list, but his content is so thick with intellectual content that it holds him back in terms of pure enjoyment. A lot of times it takes actual effort to listen to him as you get sucked into his complexity. He'll find the balance soon and move up, I'm sure.
He's the founder and CEO of Strange Famous Records. He began practicing his craft at age 8 while learning while listening to Run DMC and Public Enemy. He has degrees in communications and journalism. He's won Scribble Jam and the Superbowl MC Battle tournaments.
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