Derek J. Hernandez

Old School Vs. New School: NBA Rap Songs Then & Now

This post is part of our NBA week series, where we explore all things NBA leading up to opening night on October 31st

Now days we’re all about comparing present day stars and teams to the legends of yesteryear.

  • Could the Redeem Team hang with the Dream Team?
  • Could Kobe check MJ in his prime?
  • Would Stephen Jackson “ether” Allen Iverson AKA Jewelz in a rap battle?
I don’t know about you, but I for one am tired of all these argum…wait. S-Jax Vs. AI in a rap battle? Now we’re talking. Let’s take this up another notch even and look at other hypothetical match-ups between NBA ballers that are no longer playing but dabbled in ghetto poetics and current players that rock the mic (or at least try).


Match-up #1: “Thug Passion” – Stephen Jackson (Stak Jak) Vs. Allen Iverson (Jewelz)


Jackson’s flow –



Iverson’s flow –

Winner: Stephen Jackson

Ok. I kind of cheated here by choosing Jackson’s flows over already familiar beats even this guy could rap over, but I’m giving Stak the edge since he did a better job on Shot Caller than French Montana. Plus, I’m not really a fan of AI’s E40-esque flow and this is better than anything he recorded himself. You’re still my boy though Iverson.

Match-up #2: “Game 8 of the 2002 Kings Vs. Lakers Western Conference Finals” – Chris Webber (C-Webb) Vs. Kobe Bryant 

Webber’s flow –!

Kobe’s flow –

Winner: Chris Webber

Tyra Banks? Really Kobe?  Even though “Too Much Drama” is trash I could have just given Webber the win based on this gem from Kobe:

From Italy to the US, yes, it’s raw
I’ma search for the one that make my wealth feel poor
Who can ignore the spotlight life of Grandma

I did like that Brian McKnight track but his cameo was way too short to give him too much credit for that. C-Webb also gets props for doing a track with a DPG member and being in the Fab 5. Of course with this only being “Game 8” we’d still have to play a Game 9 and we’d probably get a repeat of this.

Match-Up #3: “Battle of the Point Gods” – Tony Parker (Tony P.) Vs. Jason Kidd 

Parker’s flow –

Kidd’s flow –

Winner: Jason Kidd

I bent the rules with this one by including Kidd. He’s not retired but he’s like 63 years old so it’s allowed. After watching those two videos do you really need an explanation as to why Kidd wins this match-up? Parker’s raps were so vile even Pepe Le Pew would cringe. At least that’s what I would say if I understood what he was saying.

Match-Up #4: “Spider-Man Vs. Superman” – Kevin Durant Vs. Shaq

Duran’ts flow –

Shaq’s flow –

Winner: Shaq

I’m giving the Hooper Hyper the edge over the Durantula on this one. KD’s just starting out and he’s actually not that bad on the mic, but Shaq’s given us way too many moments. From the terrible but totally 90’s rap battle with a little white kid on Kazaam to the “How’s My Ass Taste” Kobe diss, Shaq is probably the most relevant NBA player/rapper of all-time. Durant didn’t have a chance.


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