
Hip hop has always celebrated success —
but what happens after the rap career peaks?
In this episode of Grown Man Bars, Chad and Big Absoloot break down the 9 rappers who successfully transitioned from artists to moguls, ranking them based on business impact, longevity, ownership, and cultural power — not record sales alone.
This episode explores:
Why Jay-Z redefined what winning after rap looks like
How Dr. Dre built infrastructure, not just hits
Ice Cube’s shift from artist to executive decision-maker
Will Smith’s early escape from being boxed in
50 Cent’s mastery of attention and intellectual property
The quiet dominance of LL Cool J and Queen Latifah
And how Snoop Dogg turned personality into a business model
We also dig into:
Why the DMV doesn’t get the credit it deserves in hip hop history
What separates entertainers from builders
And why some artists stay rich while others stay famous
This isn’t gossip.
It’s grown-man conversation about money, power, and legacy.
🎧 Listen, then build your own Top 5.00:00 Introduction to Mogul Rappers02:26 Common: From Rapper to Actor and Intellectual05:32 Snoop Dogg: The Coolest Brand in Hip Hop10:52 LL Cool J: The Master of Longevity13:36 Queen Latifah: Breaking Barriers in Entertainment16:59 Will Smith: The Fresh Prince of Hollywood20:40 Ice Cube: The Visionary Entrepreneur22:58 50 Cent: The Emperor of Petty27:21 Dr. Dre: The Sound Architect29:48 Jay-Z: Rap's First Billionaire33:13 The DMV: Hip Hop's Hidden Gem36:36 Top 5 Hip Hop Legends39:21 Final Thoughts and Viewer Interaction