Yung Gleesh: DC Roots, GoGo Legacy, Gucci Mane, A$AP Rocky & Why He Chose Peace #situationswith

Yung Gleesh, Washington, D.C., is a trailblazing rapper whose raw sound and authentic storytelling helped shape the DMV’s underground rap movement. Rising to prominence with his breakout mixtapes Cleansides Finest and Your Favorite Rapper’s Favorite Rapper, Gleesh carved out a cult following through his gritty lyrics, unique voice, and unfiltered portrayal of D.C. street life. Known for his viral hit “Whippin’ the Yay” and collaborations with major artists like A$AP Mob, Playboi Carti, and Chief Keef, Gleesh became one of the first DMV artists to gain national attention during the SoundCloud era.

His influence continues to echo in the city’s new wave of rap, cementing him as a pioneer who gave D.C. hip-hop a global spotlight. With millions of streams, memorable performances, and a lasting reputation as one of the DMV’s most original voices, Yung Gleesh remains a cultural figure whose music captures the raw spirit of Washington, D.C.

In this Situations With Moon deep dive, Yung Gleesh shares his authentic story — from being raised in DC by his grandmother to finding his way in Go-Go with T.O.B. before transitioning into rap.

He reflects on the culture of DC’s streets, his early music influences, and how the city shaped his grind. Gleesh breaks down how he connected with legends like Gucci Mane, A$AP Rocky, Tyler, The Creator, and Playboi Carti, and the impact of the “Gleesh Walk” moment that took his career global.

He also opens up about the struggles of balancing family, music, and the streets, why he stepped away from the industry, and his powerful message of peace and positivity for today’s youth. This interview captures the roots, lessons, and legacy of a DC artist who lived it, influenced it, and now wants to inspire change

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Host: Maurice “Moon” Proctor
Producer: DirectedbyFour

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• YouTube (DirectedbyFour): https://youtube.com/@DirectedByFOUR
• Podcast: https://officialthismoon.podbean.com

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Timestamps:
0:00 – Intro | Moon welcomes Yung Gleesh
1:13 – Growing up in DC: raised by grandmother, father in Army, mother’s support
3:59 – Getting into the streets at 14–15 & early hustles
8:12 – Musical roots: Go-Go, radio nights & T.O.B. beginnings
14:42 – Breaking into the Go-Go scene & first big shows
18:08 – Leaving Go-Go the night Obama was elected
20:02 – Transition to rap & sacrificing for a new path
22:28 – The rise of “Gleesh Walk” & collaborations with Gucci Mane, A$AP Rocky & Tyler, The Creator
32:24 – DC vs Atlanta music scene: why unity matters
39:09 – Why Gleesh stepped back: the industry’s obsession with negativity
43:15 – All murders are senseless: survival, ego & the cycle of violence
46:14 – Generational gap: youth vs elders & what the young really want
51:00 – Gleesh reflects on influence, guilt & responsibility to the youth
55:24 – Final message: peace, harmony & finding inner balance