“Who’s Your Top Five Rappers?” Is One Of The Best Questions Ever » VSB

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“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

Panama Jackson is pretty fly (and gorgeous) for a light guy. He used to ship his frito to Tito in the District, but shipping prices increased so he moved there to save money. He refuses to eat cocaine chicken. When he's not saving humanity with his words or making music with his mouth, you can find him at your mama's mama's house drinking her fine liquors. Most importantly, he believes the children are our future. You can hit him on his hitter at panamadjackson@gmail.com.

  • Jocelyn

    “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.” Exactly! She’s decent but she’s not MC Lyte. I’m going to start asking guys the top 5. If they don’t at least have Biggie, Jay, Pac, Andre 3000, or Rakim, I can’t deal.

    • Damon Young

      Lauryn Hill doesn’t belong on that list because of lack of longevity, not lack of talent. Comparing her to MC Lyte is like comparing Penny Hardaway to Bob Cousy. Yeah, one was a pioneer with a hall-of-fame career, but a prime Penny would have literally beat Bob Cousy 100 to 0 if they played one-on-one.

      • Jocelyn

        I’m not denying Lauryn’s talent. “The Miseducation…” was almost the only CD I listened to my freshman year of college. But I don’t consider Lauryn a pure lyricist. Even during her time with the Fugees, I considered her the great singer who could spit. Penny and Bob are both basketball players who were both great in their prime.

        • Damon Young

          I always felt the opposite, that she was a great rapper who could sing. She carried The Score the way Lebron used to carry the Cavs

          • Jocelyn

            We both agree she’s great but for different reasons. This is why I enjoy the dialogue on VSB.

      • panamajackson

        Agreed. She only doesn’t make it b/c of her catalog. If she’d kept it up for a few more albums, then its a different ball game.

        • Not only that, but she only rapped on three songs on “The Miseducation Of Lauryn Hill”- that alone disqualifies her from the conversation.

        • eqjones

          No offense I consider Lauryn kinda dead. And so, out of all the dead rappers, she is the one I would most want to resurrect and hear spit again. She in my top 5, because my top 5 are MY favorites.

    • miss t-lee

      Agreed, Lauryn ain’t seeing Lyte anywhere, anyhow.

    • Mr. SD

      Yea but then you can kinda say that about Biggie as well

  • I wouldn’t put Jay, Nas, Pac, or Big in my top 5. I can’t in good conscience put Biggie there with two albums neither of which are in my top 10. And he’s not like the Jimi Hendrix in rap where he’s just so far and ahead of everyone despite his limited output. Jay Z has like the most disappointing output of any rapper with his talent. Ghost, Mos, Doom, and Andre round out my top 4.

    • panamajackson

      Anybody who puts MF Doom on their list is teetring on that contrarian ledge. I like MF Doom as well, but errrum…lol.

      Though, I would put Madvillainy up as one of the best hiphop albums ever created.

      • Mm..Food is a classic too. Mouse and the Mask is quality. Operation Doomsday is good. The second viktor Vaughn is terrible.

        • panamajackson

          I recently listened to Mm…Food b/c I remember feeling like it was a classic album when it came out. I do not feel the same way about it now.

      • Paradigm

        That chick in the Rhinestone Cowboy video tho… I always wondered who she was.. I fooled w/ MF and Quasimoto for a bit

  • Damon Young

    I have two lists: top five greatest, and top five favorite

    Five greatest
    1. Jay-Z
    2. Nas
    3. Eminem
    4. Biggie
    5. Pac

    Five favorite
    1. Ghostface
    2. Kanye
    3. GZA
    4. Jay Z
    5. Big L

    • Andrea

      I will never understand Big L. (May he rest in peace)

      • panamajackson

        It’s probably because he speaks with criminal slang. It’s just the way that he talks yo.

        • Andrea

          I understood that Ebonics reference. The only song I like.

          • panamajackson


        • jolly

          Big L’s Freestyle vs Jay…epic.

      • *cues “MVP” for Andrea*

    • Muze

      GASP. i forgot about Eminem! *goes to amend list*

    • accurate.

    • JAY_DUB

      No Rakim?

  • Pinks

    I don’t know rap well enough to contribute, so I’mma just read.

    • Damon Young

      “I don’t know rap well enough to contribute”

      If I were an asshole, I’d say that’s what’s pretty much every guy feels about women and conversations about rap.

      I’m not an asshole, though, so I won’t say that.

      • Pinks

        LOL! You wouldn’t be an a-hole, and I wouldn’t be offended. I genuinely don’t care for rap as much as RnB from the 70s-90s or reggae and soca, so I usually sit these conversations out. At most I can recite “All About the Benjamins” word for word, but that’s about it.

        True story, one time in college I liked this guy mad much and knew from one of his frat brothers (my bestie) that he was a huge Joe Budden fan. I mentioned during one of these same “who’s the best” debates that Joe was highly underrated and he looked at me with the googly eyes and I was like YES! GOTCHA NIGGA.

        A few months later, turns out the D was wack and I was mad at myself for being that girl. Ya live and learn.

      • miss t-lee
        • Rachmo


      • Simone-Elise Charles

        *Kisses your arse*

      • pls

        I think this goes back to that post on here about men picking rappers that represent THEM (you men) the best, not necessarily whether or not they’re actually the best. Because men are generally less expressive, when someone doesn’t agree with your choices, they are attacking your soul!

        it ain’t that deep for most women lol

  • Chris B.

    1. Rakim
    2. Big
    3. Nas
    4. Jay
    5. KRS

    • Kim

      BINGO!!! We have a winner here.
      Favorite New Guys: Kendrick Lamar (thought I HATE HATE HATE the single “i”), J. Cole, Childish Gambino, Joey BadA$$, and Underachivers.

  • Rachmo

    My personal faves in no particular order:
    1) Biggie
    2) Jay-Z
    3) Nicki Minaj
    4) Andre
    5) Eminem

  • miss t-lee

    “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.”


    So I guess ladies can’t have a top 5, eh?

    I see ya.

    Unfortunately as much as I love my ladies on the mic, none make my Top 5. I would throw Kim on there, but I know most of her early stuff was written by Big, and he is in my Top 5, so it’s like she’s on there.

    My top 5

    1. Scarface

    2. UGK (I include them as one, no questions, please)

    3. Jay-Z

    4. Biggie

    5. Ghostface

    • panamajackson

      See for the first time I ever, I said most. and the reason is b/c I QUERIED A ton of women I know and most couldn’t care less about the convo. You wouldn’t be one of them. lol. I’ve been apart of top five arguments with women. It’s like either you care and are ’bout that life or y’all dont give a sh*t at all. At least in my experience.

      • miss t-lee

        PJack, it’s more than you think. I understand it might be this way among your circle of friends, or folks you work with or other acquaintances. However, as we’ve had this discussion before you can’t keep discounting us that do love rap because of the few ladies (in the grand scheme of things) that you know personally.

        • Aly

          It reminds me of the men who believe women don’t like sports. Just seems like an outdated notion.

          • miss t-lee


        • panamajackson

          I think you’re assuming I only knew a few ladies. I’ve been around the world and i-i-i…point is, I know what you’re saying. But if the vast majority of us have the same experiences, we can’t all know the exact same women.

          But…I dont think hiphop is just for dudes at all. I love it when women jump into the fray.

          • miss t-lee

            Lisa Stansfield, eh? *snickers*

            I’ll allow it.

            Gonna ignore your other point though. Happy Friday! :))

            • panamajackson

              It’s never not a good time to toss Lisa Stansfield into a convo.

    • Tish Harris

      Basically, Miss t-lee’s list is the most accurate of all, sans Ghostface.

    • “Unfortunately as much as I love my ladies on the mic, none make my Top 5.”

      No MC Lyte, Miss T-Lee? Shame on you, LOL!

      • miss t-lee

        Top 10 yes. Top 5 no.

  • Simone-Elise Charles

    What does it mean if they put Ja Rule in the top spot? My first thought was “That ninja who screams at everbody?” But then again there are no rappers in my top five

    • panamajackson

      If somebody puts Ja Rule in their top spot and they’re not from Queens, I’m legit questioning everything about them. And mind you, I liked Ja.

  • Andrea

    I think I get to make Nina Simone my number 1. Just cause she’s in a lot of rap songs. So. It counts.
    My list : Dres, Prodigy, Mos&Kweli, Prince Paul, Chuck D

    • panamajackson

      That is the first time I have EVER seen Dres from Black Sheep on anybodys’ list of favorite or greatest. lol. You must be from LI.

      • Andrea

        I am from LI. And I was in love with him. Very Deeply. I used to call him and hang up. Ohhh how I loved to listen to him breathe. I think I used to kiss the sticky note his phone number was written on. That’s the only person I’ve ever went full Mike Jack on. When I first met him. I had a panic attack…Began to cry…hyperventilated….and then got my ass beat my sister for embarassing her at work. Ahhh…..kids will be kids.
        “Wishes which you wish upon you wish were more than wishes.
        If I wish not to work harder study not then I wash dishes
        Wish while I wash, the water hot gets colder
        Black I’m saying that in fact the dishes gets clean and I get older
        Seemingly so, the dishes will grow to dishes are beyond me
        Lost my wish and broke a dish so now I’m wishy washy
        Understand foundation, create my own creation
        If dumb and pumping jump, then get no ovation
        But only restriction, bull pens and lot of friction
        I then wash a dish without pay. Boom! N.W.A”
        Is BRILLIANT. I’m rusty :(

        • panamajackson

          I ain’t saying that aint deep. I’m just saying that he rarely makes anybody’s list. lol

      • Andrea

        Y’all don’t approve Black Sheep lyrics? This is censorship mane. #BlackSheepMatters #TheyShutItDown lol

        • panamajackson

          I like Black Sheep songs. I will never confuse Dres for a great rapper.

  • 1. Black Thought – sound and workman like but not flashy.

    2. Biggie

    3. Ghostface

    4. Three Stacks

    5. Pos from De La

    Jay, MJG, Monch, and Killer Mike are my bench players.

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