Don Trip & Starlito slide through the Diggin’ lounge with stories, jokes, and deep cuts. From MJ’s tiger flex on Thriller to the raw energy of Outkast, DMX, and Master P, the Step Brothers go crate for crate on the albums that raised them — and the game they soaked up along the way.
In this laid-back yet deeply personal Diggin’ session, the Step Brothers revisit the golden era of mixtapes, the raw energy of gangsta rap, and the lost art of storytelling in hip-hop.
They break down the bootleg era, the Grey Goose days with Jeezy, and how J. Cole’s KOD hit different on a late-night jog. There’s real talk on fatherhood, why they still build albums like full-length films, and how Lil’ Kim’s Hardcore changed how covers were done — forever. Don even shares the one concert he’s ever been to (spoiler: it wasn’t rap), while Star remembers learning about Master P the hard way. The conversation covers respect, identity, grief, growth, and the pressure of staying independent in a business that doesn’t care about nuance.
0:00 — Don Trip Picks Thriller, Talks MJ’s Iconic Album Art
0:56 — Diggin’ Begins: Step Brothers Reflect on Music & Memory
1:04 — Why The Black Album & Jay-Z’s ‘Allure’ Still Hit
1:15 — TLC, Tupac & the Soundtrack to Growing Up
2:22 — Jogging to J. Cole: How KOD Spoke to Don Trip
3:07 — Young Jeezy, Grey Goose & First Big Collaborations
3:56 — Isaac Hayes & the Sound of Sampling: Footsteps in the Dark
4:33 — How Bootleg Tapes Raised a Generation
5:03 — Outkast’s ATLiens: The Album That Changed Everything
5:48 — DMX, Lox & the First Time Hearing ‘Money, Power, Respect’
6:38 — The Legacy of Lil Kim’s Hardcore Artwork
7:20 — Dream Collabs: Kendrick, Cole, Jhene Aiko, Miguel
8:53 — Master P, Chris Brown & DIY Music Hustle
10:59 — Concert Stories: Janine Aiko, The Eagles & Floor Seats
12:08 — Stevie Wonder’s ‘All I Do’ & the Power of Feel-Good Soul
13:01 — Favorite Music Videos: Mobb Deep, Lil Kim & Dead Prez
Speak On It!