DMX's 1999 Woodstock set is called one of the greatest hip hop performances ever. Rello, Kunda & Miss Angie break down why — plus the Aaliyah connection.

On this episode of Circle The Block, hosts Rello, Cunda, and Angie circle back to one of hip hop's most legendary live moments: DMX's 1999 Woodstock performance, widely regarded as one of the greatest hip hop sets of all time. From there, the crew dives deep into DMX's dominance on the 1999 Hard Knock Life Tour alongside Jay-Z, Method Man & Redman, DMK, and more — including the wild story of the "Million Dollar Bet" that led DMX to record his double-platinum sophomore album, Flesh of My Flesh, Blood of My Blood, in just 30 days.

The conversation turns personal and nostalgic as the hosts share their own DMX memories — from getting an A in English class off a DMX prayer, to debating DMX's underrated acting career in cult classics Belly and Romeo Must Die. That leads into a heartfelt tribute to Aaliyah, her film debut, her chemistry with DMX on screen, and her lasting influence on 90s and 2000s pop culture.

As always, the episode is loaded with the crew's signature odds segments — placing bets on which artists drop albums in 2026 (Beyoncé, Jay-Z, Kendrick Lamar, Taylor Swift), the 2026 Mercury Prize, and the 2026 box office race between Spider-Man: Brand New Day and Avengers: Doomsday. It's culture, nostalgia, comedy, and hip hop history — all in one sitting.

New episodes of Circle The Block drop every week — hit subscribe and turn on notifications so you never miss a conversation about the music, movies, and moments that shaped us.

00:00 – Intro & warm-up with the crew

04:12 – DMX's legendary Woodstock '99 set

09:18 – The 1999 Hard Knock Life Tour breakdown

18:37 – Tour trivia: the Cincinnati snub & Pittsburgh snowstorm story

20:54 – Who's dropping an album in 2026? (Beyoncé, Jay-Z, Kendrick Lamar, Taylor Swift)

24:47 – Rough Ryders anthems & DMX's raw storytelling

25:33 – DMX on Drink Champs: recording two platinum albums in one year

26:03 – The numbers: It's Dark and Hell Is Hot vs. Flesh of My Flesh, Blood of My Blood

29:31 – The DMX prayer that got a host an A in English class

31:58 – The Million Dollar Bet with Def Jam

33:00 – 2026 Mercury Prize

34:21 – DMX the actor: Belly & Romeo Must Die

37:07 – Aaliyah's film debut and her on-screen bond with DMX

41:52 – The Aaliyah legacy debate

46:56 – 2026 box office predictions

47:07 – Bishop Kunda's closing sermon

49:42 – Final thoughts & outro

Subscribe to Circle The Block: https://www.youtube.com/@CircleTheBlockPodcast

Listen on Spotify: https://open.spotify.com/show/2GcCyRJN4vtNPei0UtRg7D?si=f21fff83d20f4280

Listen on Apple Podcasts: https://podcasts.apple.com/us/podcast/circle-the-block/id1790258938

Instagram: instagram.com/thecircletheblockshow

ABOUT CIRCLE THE BLOCK

Circle The Block is a culture and nostalgia podcast hosted by Rello The Saya, Kunda, and Miss Angie, where hip hop history, throwback pop culture, and current entertainment news collide. New episodes weekly.

Hosted on Acast. See acast.com/privacy for more information.