I Only Listen to 90s Music: Is That Dave Chappelle? (Usher, 90s Dating, Diddy Watch, Guest Verse Slayings, Home Alone Reboot, and More)

The crew is back and they take an unscripted journey through classic 90s hip-hop and R&B, pop culture nostalgia, and spirited debates!

In this episode, the team breaks down the true cultural origin of Air Force Ones—from Harlem’s "uptowns" to Nelly and the St. Lunatics taking the classic shoe global. They also dive deep into classic rap rivalries and guest feature "homicides," analyzing iconic verses where guest MCs completely stole the show—including Eminem on Jay-Z’s "Renegade," Nicki Minaj on "Monster," and Kendrick Lamar’s internet-breaking verse on "Control."

They examine Questlove's theory on how drug eras shaped the sound of hip-hop over time, revisit the legendary choreography behind BBD's "Poison" with Brooke Payne, and debate whether Usher’s Confessions tops R. Kelly’s catalog as the greatest R&B album of a generation. Top it all off with hilarious behind-the-scenes stories about Video Soul, Donnie Simpson, and James Brown's eccentric antics! Chapters

00:00 – Usher Concert drama with women getting pulled on stage and was that Dave Chappelle at the Usher concert? 08:54 – Did Nelly or Jay-Z Make Air Force Ones Popular? 12:28 – Diddy Watch: Post-Release Speculation & Who Gets the First Interview wiith Sean Combs 23:38 – Simple 90s Dating and. Questlove’s Drug-Defined Hip-Hop Eras 33:20 – Lyrical Homicide: Rap Collaborations Where Guest MCs Outshone the main artist 39:55 – Floods, Lost Tapes, & Busta Rhymes’ Breakthrough on "Scenario" 42:33 – Remy Ma, Nicki Minaj on "Monster", & Iconic Remix Verses 45:23 – Canibus, Lil Kim's "Quiet Storm", & The Firm's "Desperados" |48:35 – Kendrick Lamar’s "Control" Verse & Rap's Biggest Mass Murders 56:33 – The Legacy of 90s Dancers: Brooke Payne & Choreographing BBD’s "Poison" 1:06:15 – Debating The Wood Sequels & How to Be a Player 2026. 1:11:29 – The Home Alone Reboot Concept Starring Macaulay Culkin 1:16:24 –  Richard Pryor, Freddie Prinze Sr., & Pam Grier 1:24:45 – The Ultimate R&B Debate: Usher’s Confessions vs. R. Kelly & Jodeci 1:45:58 – Donnie Simpson talks about  funniest moment on Video Soul ....James Brown’s On-Set Mishaps & Money-Burying Antics

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