Last Updated: 09. 22. 2026
My Top Five Rappers
- Kendrick Lamar
- Eminem
- Jay-Z
- Biggie
- Pusha T
Honorable Mentions: Tupac, Method Man, Black Thought
G.O.A.T List
- Kendrick Lamar
- Andre 3000
- Nas
- Rakim
- Tupac/Biggie
Honorable Mentions: Jay-Z, MF Doom, Ghostface, LL Cool J, Scarface, Ice Cube
Notes On “Top 5”
I love hip-hop. To this day, nothing can put me in a better mood than some 808s, a dance floor, and some braggadocios entendres.
Anyone who is even moderately tapped into the culture will eventually be asked who the greatest rappers of all time are. There are no right answers, per se, but there are certainly wrong ones— and your answers say a lot about you.
A person’s top five isn’t meant to be correct as much as it’s meant to force a discussion (and real fans will always discuss). Five is too small to encompass all the greats, but hip-hop is a sport as well as an art— and that means someone needs to be on top. Without that spirit, it’s not hip-hop.
That being said, I do think it’s a hip-hop fan’s right to delineate the boundaries of this conversation. There is a big difference between my top five and who I think is top five in a more “objective” sense. MF DOOM is a thousand times the rapper that Will Smith was, but I can still go bar for bar on I’m All That because Fresh Prince was a “clean rapper” and the Homebase album was the only one my parents would let me listen to as a child. Will Smith didn’t make my list, but you get the gist.
First, I am from Southern California and my bias for West Coast is heavily evident in my 6-20 spots (not disclosed… yet), as well as my producer choices, even if it’s not clear in my 1-5.
Also, choosing just five is difficult enough, so there is no way that I was going to rank them. The above order is completely incidental. My reasoning for my personal top five will, hopefully, be illuminated over time as I write about the music I am listening to.
Lastly, I reserve the right to change my mind. If and when this changes, I will update the timestamp at the top of the page. If you disagree with my list, please reach out and let me know. I’d be happy to debate.
Some Quotes
“Here’s the order of my list that it’s in,
It goes: Reggie, JAY-Z, Tupac and Biggie,
André from OutKast, Jada, Kurupt, Nas, and then me“
— Marshall Mathers, ‘Til I Collapse
“I love when they argue the hardest MC
Is it K-Dot? Is it Aubrey? Or me?
We the big three like we started a league, but right now, I feel like Muhammad Ali.“
— Jermaine Cole, First Person Shooter
“Smoking on top fives
Motherfuck that album, fuck that single, burn that hard drive
Ain’t nobody safe, when I come, I’m killin’ everybody that’s outside
Yeah, Kanye changed his life
But me, I’m still an old-school Gemini.“
— Kendrick Lamar Duckworth, Family Ties
“I’m from where the beef is inevitable, summertime’s unforgettable
Boosters in abundance, buy a half-price sweater new
Your word was everything, so everything you said you’d do
You did it, couldn’t talk about it if you ain’t live it
I’m from where n_ggas pull your card, and argue all day about
Who’s the best MCs, Biggie, Jay-Z , or Nas?“
— Sean Carter, Where I’m From
P.S. — If you’re interested, N.O.R.E. forces the guests on his podcast to choose “this or that” rapper, or they take a shot. Someone made a playlist that collects their answers that you can view here.
About the Author:
Bradley Andrews is a hopeful rabble-rouser on a mission to inspire the world. Stay in touch with what he’s doing by subscribing to a weekly digest of his activity through micro.blog. This will send you writing, photos, and other curiosities that you are guaranteed to love.
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