Entertainment Lawyer Bob Celestin: Inside Uptown Records, Protecting Pop Smoke’s Legacy, and AI
Entertainment attorney Bob Celestin is a 30-year veteran of the music business
BIG CED sits down with entertainment attorney Bob Celestin — a 30-year veteran of the music business who made an immediate impact at Uptown Records under Andre Harrell before building a career representing some of the biggest names in Black music.
Bob takes us from his days as a Yale radio DJ discovering hip-hop in real time, to working alongside a young Sean “Puffy” Combs, to becoming VP/GM at Uptown Records, to building his own practice representing artists through some of the industry’s most emotional moments — including managing the posthumous legacies of XXXTentacion and Pop Smoke.
We also get into the real conversation everyone in music is having right now: AI. Bob breaks down how AI is changing contract drafting, why artists still need to register their copyrights the old-fashioned way, and what’s happening behind the scenes as major labels negotiate AI licensing deals with companies like Udio and Suno.
This one covers the business, the history, and the heart behind entertainment law.
Topics covered:
- Bob’s path from Yale pre-med to entertainment law
- Getting into radio and discovering Hip-Hop’s origins
- Landing at Uptown Records and working with Andre Harrell
- Puff Daddy’s legendary work ethic as an intern
- Untouchable Entertainment, Eddie F, and working with LaFace
- Mentorship under Louise West and building his client base
- Managing the posthumous estates of XXXTentacion and Pop Smoke
- Why every artist needs a trust, not just a will
- AI’s impact on music creation, copyright, and contract law
- Major label negotiations with Udio and Suno
- Advice for new artists: “Copyright Your Sh*t” (CYS)
Follow Bob Celestin on IG: @BobCelestin
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Timestamps
0:00 Intro — welcoming Bob Celestin
1:03 Bob introduces himself — 30 years as an entertainment attorney
3:27 What still motivates him after all these years
3:36 Haitian immigrant roots and the emphasis on education
4:25 Going to Yale for pre-med
5:14 Meeting DJs on move-in day and joining Brothers Unlimited
7:02 Becoming an on-air personality at WYBC
8:36 Meeting label execs who tell him to become a lawyer, not a DJ
10:42 A course on Black culture that changed his perspective
14:05 Why protecting Black creators drives him
16:00 Why creativity often comes from struggle
16:42 Black oral tradition and expression through art
18:44 Visiting a slave fort in Ghana
22:51 Did he know Uptown would become what it became?
23:13 Getting to Uptown Records via Reggie Hudlin
26:44 First meeting with Andre Harrell
27:47 Building Uptown Records from his apartment
28:50 Puff Daddy's work ethic as an intern
31:02 Untouchables Entertainment with Eddie F
31:45 Working with Louise West, artist advocacy
33:47 How he ended up representing Genuine
39:47 Reputation, lawyers getting a bad rap
42:36 Artificial intelligence in the music business
45:38 "Copyright Your Sh*t" — protecting your work
48:16 How AI has helped and changed his practice
49:07 Representing the estates of XXXTentacion and Pop Smoke
51:37 Advice for artists — trusts, life insurance, planning ahead
53:36 Money management lessons from the pandemic
55:06 Final words and where to find BobKeywords / Tags
entertainment attorney, Bob Celestin, Uptown Records, Andre Harrell, Puff Daddy intern, Sean Combs, entertainment law, music industry lawyer, XXXTentacion estate, Pop Smoke estate, AI music, AI copyright, Udio Suno lawsuit, copyright your music, Yale University, Black entertainment lawyers, Louise West, Eddie F, Untouchables Entertainment, LaFace Records, music publishing, artist advocate, posthumous music legacy, hip hop history, New Jack Swing, Teddy Riley, music business podcast, Big Sad Industry Co-Sign
Hashtags
#EntertainmentLaw #UptownRecords #AndreHarrell #MusicIndustry #AIinMusic #CopyrightYourWork #HipHopHistory #BlackExcellence #MusicBusiness #XXXTentacion #PopSmoke #BIGCED #TheIndustryCoSign
