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Jimmy Poindexter raps across “Yonkers” to “Bed Chem” on 9-Minute “A CRUEL Freestyle” [Music Video]

  • August 20, 2025
  • Deaundre Dixon
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Jimmy Poindexter, the 27-year old California rapper and producer shines a spotlight on his lyrical prowess, rhyming over rap classics like Nas’ “Still Dreamin’” or Tha Dogg House’s “Cali iz Active,” and also over more contemporary joints like Kendrick Lamar’s “Squabble Up” and Clipse’s “P.O.V” from their most recent foray Let God sort em Out.

The 9-minute declaration tackles subjects ranging from Jimmy’s upbringing with lines like “Have you ever caught your momma sniff a line While you lookin’ for a snack—Walk right back into your room like it was fine?” to the seeming lack of attention designated to talented underground rappers such as himself with lines like “Watchin’ these boys who couldn’t hang get prized with double XXL covers— f*** the numbers.”

The freestyle is accompanied by a DIY, Tyler, The Creator-esque visual in which Jimmy spits before a mic in front of a green screen, occasionally splitting the screen to hone in on details such as his chain, his eyes, or even just blank space which is used to promote his most recent album Cruel World released May 23, 2025.

A thematic through line sewn into the fabric of the track is Jimmy’s pride at being a product of rap culture; a unique, one-of-one emcee, able to stand his ground against anyone from today’s biggest stars to incredulous internet trolls. These themes are explored not only in the diverse beat selection, but also in lines like “…take this serious bigot talkin’ sh** online them bots come in a myriad I caught ’em out in public, p**** n**** got his period” or “Real ones get the money and acclaim rap circles ’round the lames student of the game, I’m proud to be one.”

It's clearly not all talk with bars like “…Like Syndrome, I go nutty, I stand outside the crowd missed a shot or two, okay, I understand it now It’s hard to share a unique perspective they say I’m not allowed, Joey, I grew up on 1999, I’m very proud but now anything north of 30 is gettin’ 86’d”  that show just how deliberate Poindexter is with his words; deliberation that has manifested itself in a pen rivaling the likes of contemporary industry giants. 

However, even while rivaling the lyrical skill of his contemporaries, Jimmy struggles to distinguish himself, often wearing his influences boldly on his sleeve.

Whether intentional or not, the clear Tyler, The Creator–inspired visuals and occasional Kendrick-esque delivery make some of Jimmy’s declarations about uniqueness and individuality feel a bit moot.

Poindexter's albums reveal a clear vision and impressive lyrical skill, but until he fully comes into his own sonically, visually, and stylistically, he risks remaining in the shadow of his influences.

 

Connect with Jimmy Poindexter: Instagram | X | YouTube

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  • A Cruel Freestyle
  • freestyle
  • Freestyle Rap
  • hip hop
  • Jimmy Poindexter
  • music video
  • New Music
Deaundre Dixon

Deaundre Dixon a writer from Phoenix, Arizona with a passion for music and film. In his free time, he enjoys reading comics and thinking about stories.

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