Bad Boy Entertainment: Can’t Stop, Won’t Stop

We can’t tell the story of hip-hop without mentioning Diddy and the record label he started. Bad Boy took off in 1993 after Puff was fired from Uptown Records. He brought TheNotorious B.I.G. with him from Uptown Record, and signed a 50-50 deal with Clive Davis’s Arista Records, and it was off to the races.

Bad Boy survived the tragic fallout of the East Coast vs. West Coast rivalry, and reached even bigger heights after Biggie’s death. Puff began to rise as a solo artist, but did the rest of the artists suffer as a result?

Friend of the pod, Zack O’Malley Greenburg, joins me on this episode to cover 30 years of Bad Boy Entertainment. Here’s what we hit on:

0:13 Sean Combs come-up story
3:11 Diddy breaks in with Uptown Records
6:47 Starting Bad Boy Records
12:07 What sets Diddy apart
19:00 How Diddy controlled the narrative
22:00 Bad Boy’s formula for success
27:08 East Coast vs. West Coast rivalry
35:35 Bad Boy’s historic 1997-98 run
43:39 Bad Boy curse?
46:46 Diddy’s reputation compared to Cash Money
52:53 Best signing?
53:20 Best business move?
55:21 Best dark horse move?
58:19 Missed opportunity?
1:06:03 Possibility of biopic?

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