Dr. Umar Johnson sits down with Loon for an explosive conversation on Michael Jackson, Drake’s UMG battle, Jay-Z, Netflix, Floyd Mayweather, Farrakhan, Black leadership and more.

Dr. Umar Johnson returns to It’s Up There with Loon for a wide-ranging conversation that quickly moves into Michael Jackson, Drake, Jay-Z, the music industry, Black leadership, money, power and what happens when major Black figures collide with powerful institutions.

Loon presses Dr. Umar on Michael Jackson following Netflix’s Michael Jackson: The Verdict, leading to a deeper debate about Jackson’s 2005 acquittal, the accusations that followed him, Sony, his legacy, his cultural impact and whether the public has ever been given the full Michael Jackson story.

The conversation then takes an unexpected turn toward Drake.

With Drake currently battling Universal Music Group through his ongoing appeal and using Michael Jackson-inspired glove imagery for Iceman, Loon asks whether Drake could be signaling something deeper about his own position in the music business. Dr. Umar responds with a serious warning about fame, power, ownership and what artists should do when major conflicts begin happening behind closed doors. Drake’s appeal against UMG remains active in 2026, while his Iceman artwork has publicly drawn comparisons to Michael Jackson’s famous glove.

Dr. Umar and Loon also get into Jay-Z, Kanye West, Dame Dash and what may happen behind the scenes when artists become powerful enough to challenge the structures around them. Umar discusses why he believes major public figures should be more open about the battles they face instead of allowing the public to discover the story afterward.

But the episode goes far beyond music.

Loon and Dr. Umar debate Floyd Mayweather and wealth, 50 Cent, Michael Eric Dyson, Cornel West, FBA and the Freedmen debate, reparations, Marcus Garvey and the Black Star Line, Minister Louis Farrakhan, Muammar Gaddafi, Black nationalism, the assassination era of Black leadership and Umar’s continuing plans for FDMG Academy.

This is another unfiltered conversation between Dr. Umar Johnson and Loon about culture, history, celebrity, power and the future of Black America.

Watch the full conversation and tell us where you agree — and where you think Loon or Dr. Umar went too far.

Subscribe to It’s Up There with Loon for more long-form conversations, cultural commentary and interviews.

It’s Up There with Loon — conversations that go where everybody else stops.

The conversation closes by debating Drake versus Michael Jackson, streaming-era statistics versus cultural impact and whether numbers alone can capture greatness.

00:00 — INTRO — Dr. Umar Returns to It’s Up There

02:30 — Michael Jackson: Netflix, the Trial & What Really Happened

08:00 — Was Michael Jackson a Prophet?

11:30 — Michael Jackson vs Elvis, Sinatra & How History Gets Rewritten

15:30 — Prophets, Sacrifice & the Assassination of Black Leaders

19:30 — Farrakhan, Gaddafi & the Billion-Dollar Offer

24:00 — Malcolm X, MLK, Fred Hampton & the Era of Assassinations

29:30 — Floyd Mayweather’s Money Problems, 50 Cent & Who You Trust

34:00 — FBA, Freedmen, Reparations & Black Identity

39:00 — Cornel West, Michael Eric Dyson & Black Intellectual Leadership

43:00 — Marcus Garvey, Black Nationalism & the Black Star Line

47:00 — Jay-Z, Kanye West & What Happens Behind Closed Doors

52:00 — Why Dr. Umar Calls Dame Dash Valuable

55:30 — Drake’s Black Identity, Kendrick Lamar & the Culture

1:00:30 — Drake vs UMG — Is He Following Michael Jackson’s Path?

1:04:30 — The Michael Jackson Glove & Drake’s Iceman Message

1:08:00 — Why Dr. Umar Warns Drake to Be Careful

1:12:30 — FINAL WORDS

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