"Who's Your Top Five Rappers?" Is One Of The Best Questions Ever


A few weeks back I had the pleasure of seeing the movie Top Five starring Chris Rock and my #bae for life, Rosario Dawson. Was it a good movie? Eh. It wasn't bad. It's high points were hilarious but it isn't exactly going to change anybody's life. When it comes to Chris Rock movies, there's usually "ehhhhhhhh" and "hmm, that wasn't terrible". This falls in the "that wasn't terrible" realm. But considering how much of a truth tour Chris Rock has been on lately I'm almost inclined to go see it again just to support him.


The title of the movie references a questions thats asked in the movie, "who are your top five rappers of all time?" The trailer makes it seem like this is a vital component of the movie. It is not. After seeing the movie I actually wondered why they titled it Top Five. But hey, the story of my life will probably be titled Tiddy Sprinkles so who am I to judge?

That question, though, might be one of the most popular and most constant questions in my life, and one of the most important questions you can ask a Black male (probably any male but I don't know enough "other" males personally to know how those conversations go) between the ages of 18-44. In fact, for ladies, after asking him if he's married, has any kids, has bad credit, or if he's either dating or if anybody thinks they're dating him, asking him his top five favorite/greatest rappers of all time will tell you everything you need to know. In fact, you can probably put that first, because if that list is trash then the other questions shouldn't matter.

Then again, women will almost always believe in the possibility of the potential of what might be of what could be bitch I might be in love with the coco so ask all of the questions, please, ladies.

Now, I'd contend that unless most women are hip-hop heads they're not even thinking to ask this question, whereas I honestly cannot tell you how many arguments I've had that surround it. Hell, I vividly remember an argument from my sophomore year of college when one of my boys tried to put Q-Tip in the top five best rappers of all time debate which ended up being the reason I missed some classes that day. Or my other boy who I'm presuming still argues, to this day, that LL Cool J deserves a spot purely off of longevity and (pseudo) relevance.

Since high school hallway debates, the top five question has been part of the Black man experience. And thus, you can learn a lot from a man based on who is in his top five. Obviously, I don't have the algorithmic, or actuarial expertise to run a shit load of permutations that explain what a combo of Andre 3000, Nas, Biggie, Webbie, and Silkk The Shocker means, but I do know that anybody that puts Silkk The Shocker into their Top Five is probably going to rob you. They are not to be trusted. Also, that would be one of the most confusing top five lists of all time. Clearly a southerner, but possibly one who moved from, like, Lawrence, Massaschusetts and was only allowed to bring two albums from home and they were It Was Written and Life After Death. (Nobody whose favorite album was Illmatic would ever have Webbie in their top five. I have no proof, but I'm calling this one impossible. Also, nobody you speak to should have Webbie in their top five.)

Another reason why asking this question can tell you so much is because every dude has legitimately thought about it. Okay, not every dude. But if he has a top five, he's spent considerable time thinking about it despite pretending like he's always thinking about it on the spot in these debates. The only reason we ever hesitate is because we're about to throw a name in there that is either a) ridiculous (like U-God) forcing you to immediately do the authentic Black community sign of WTF - hands up like we got shot or run around loudly; or b) our favorite rapper and we're afraid somebody will tell us they're trash and deserve no consideration (like Lil Wayne). Or lastly, we just like to pretend we're really thinking about it.


For instance, if you ask me who my top five are I'll say 1) Jay 2) Biggie 3) Nas 4) Andre 3000 and um….hmmm….5) Pac. See, even I had to think about it. And I'm writing this. Now of course, this list is debateable as hell. The first three usually end up on most people's list in some order who were born in the late 70s or early 80s. In fact Pac usually is part of that top 4 and the part of the country you're from determines the order. It also tells you that I'm a child of the 90s era of hip-hop because despite all of them except 'Pac and Biggie releasing albums in the 2000s (because of reasons #shotsfired…damn…that was a pun and a true statement) for some reason, we tend to attach them to their seminal works, which were all released in the 90s. I'd bet not a single person born in the 90s would put any of them in their favorite rappers of all time top five, which tells you something. If a dude lists a top five that doesn't include Jay, Nas, Biggie, or Pac, he's either WAAAAAY too contrarian and you will argue about EVERYTHING or he's under 25 and thinks Lebron James is the greatest basketball player of all time.

Also, and this might be contentious, but I think Jay is the greatest rapper of all time. However, I think Biggie was a much better rapper than Jay. Easily. Hands down. Sometimes when I listen to Biggie songs I am actually in pure awe at how he constructed his verses and the way he thought. I love Jay, but if I was a rapper, I'd want to be Biggie. I don't think Biggie would have the same career Jay has had he lived because I think Puff would have ruined it. But from the pure rapper standpoint: Biggie.


If you ask most women they'll probably toss some women rappers in the fold, which works and I respect in honor of the Female MC Struggle. Guys who like to let you know they're enlightened might throw Lauryn Hill in there despite the fact that she absolutely does not belong. Anybody with Lil Wayne (a very real possibility) is probably 30 or under. A person who tosses Kanye into the equation - also a very real possibility given his output and contributions to the game - wants you to know that they're artsy and will possibly pay $200 for a white tee.

There are folks who will have lists that include Rick Ross. It's entirely possible that dudes with him on their list will embellish the truth a bit or count Queens as books in spades. Never trust a person who counts non-spade Queens as books in spades. Seriously. Like, for real. Which is important to know. It's why a personal top five question about hip-hop is one of the conversations almost every group of male friends has had at some point. If a dude tells you he doesn't know because he doens't listen to rap there's a good chance the texts to hang become fewer and far between as he also goes to find a group of friends whose top five discussions don't include one about rappers.


A person's top five says a lot about who they are as a person and their musical tastes. And  musical tastes tell me everything I need to know about a person. I truly believe this. Everybody's entitled to their opinion. But opinions, just like shoe choices, drink choices, and brand loyalties are meant to be judged.

Judge wisely my friends.

PS. Nothing about a man's rapper choices will tell you if he'll cheat on you. Sorry.

Panama Jackson is the Senior Editor of Very Smart Brothas. He's pretty fly for a light guy. You can find him at your mama's mama's house drinking all her brown liquors.


Damon Young

And the most underrated rapper of all-time, the guy who never, ever, ever shows up on anyone's best ever list but has been consistently spitting fire for almost two decades?

Busta Rhymes