Brooklyn's Finest: The Making Of Reasonable Doubt by Jay-Z
Jun 25, 2026 · 35 min · 9 segments
In our second episode, we look at the process of making the *Reasonable Doubt* album, the internal struggles, signing to Payday Records, Roc-A-Fella Records renting their first office space, and…
Pain in da AssGuestChristopher MitchellHost
Sumit SharmaHost
Abdul Malik AbbottGuest
DJ Clark KentGuest
Ski BeatzGuest
Jaz-OGuest
Rob MarkmanGuest
Dart AdamsGuest
David LotwinGuest
SK VibemakerGuest
Joe QuindeGuest
Sean KantrowitzGuest
After fascinating hip-hop heads with songs like I Can't Get With That and In My Lifetime, Jay-Z inked a deal with Payday Records, which ultimately proved to be short-lived.

It was DJ Premier who connected the dots between Patrick Moxie and Rockefeller Records.

In a 1999 interview with Yahoo Music, Jay spoke on his time on Payday Records by saying,
Using the money from the deal with Payday, Jay Damon Biggs rented an office on 17 John Street, which was at the time a low-rent part of downtown New York, adjacent to the financial district.
The only thing left to do was to start recording the Reasonable Doubt album.


And I'm not an edgy, primo type of producer, you know? I mean, I come from like a musical background, families.

After fascinating hip-hop heads with songs like I Can't Get With That and In My Lifetime, Jay-Z inked a deal with Payday Records, which ultimately proved to be short-lived.

It was DJ Premier who connected the dots between Patrick Moxie and Rockefeller Records.

In a 1999 interview with Yahoo Music, Jay spoke on his time on Payday Records by saying,
Using the money from the deal with Payday, Jay Damon Biggs rented an office on 17 John Street, which was at the time a low-rent part of downtown New York, adjacent to the financial district.
The only thing left to do was to start recording the Reasonable Doubt album.


And I'm not an edgy, primo type of producer, you know? I mean, I come from like a musical background, families.
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