SHOW / EPISODE

The Dear Mama Episode — Lil Durk, Meek vs Ak, Albums With No-Skips Lists, Best Storytelling Rappers | Ep. 289

2h 8m | Sep 21, 2026

The Funniest Podcast On The Planet is back with What You Thought #289 | The Dear Mama Episode.

At 00:08:00, the crew breaks down State RICO vs Federal RICO, including why the federal version is viewed as a much tougher fight. At 00:12:00, it’s Meek Mill vs Akademiks, where the argument quickly becomes less about tweets and more about whether Ak has ever actually had to physically back up all that disrespect. Pop looks at the evidence and delivers a completely scientific conclusion based on head circumference. 

At 00:34:00, the conversation turns to O Block and terrorism comparisons, followed by the decoy-plane discussion at 00:41:00. At 01:30:00, the crew gets into the second trial, before boxing takes over at 01:36:00 with Boots Ennis, Terence Crawford and the money attached to a Canelo fight. Pop’s question is simple: if fighting Crawford risks the undefeated record for relatively small money, why rush it? 

At 01:49:00, the crew debates which rapper has the fewest skips in their catalog. Darnell immediately objects to Illmaticbeing in the conversation because the album is so short—right before Ammar pulls up the actual tracklist and forces everybody to revise the math. Receipts remain the undefeated seventh member of the podcast. 

At 02:05:00, the crew builds a list of the best storytelling rappers: Biggie, Nas, Jay-Z, Slick Rick and Cole all enter the conversation before Darnell brings up Tupac. That leads to the argument that gives the episode its name: is “Dear Mama” actually a story, a poem, a chant, or a homage? The episode ends exactly how all serious literary criticism should end—with Tupac impersonations. 

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