Club Shay Shay – Big Daddy Kane (Part 1)

Host: Shannon Sharpe
Guest: Big Daddy Kane
Date: September 24, 2025

Overview

In this rich and candid episode of Club Shay Shay, Shannon Sharpe sits down with legendary rapper Big Daddy Kane to reflect on his four-decade career, the roots and evolution of hip hop, his relationships with icons like Tupac, Biggie, and Jay-Z, and the culture-shaping role of Brooklyn. Kane offers trademark wisdom about lyricism, authenticity, collaboration, money, competition, and the endurance of musical legacy in the streaming age. The conversation is animated, full of stories, laughter, lessons, and deep respect for hip hop’s past, present, and future.

Key Discussion Points & Insights

1. The Enduring Legacy and Humble Beginnings of Big Daddy Kane

• Kane's Reaction to Accolades (04:27): Kane downplays the 40-year span (“It’s only been 37… but it’s all good. I take it.”), expressing gratitude for the recognition and the journey from childhood passion to cultural icon.
• Finding His Voice in Brooklyn (06:42–08:00): Kane details how the street vernacular of hustlers and the unique Brooklyn energy shaped his lyricism:
  • “I just want to have that slick talk, you know?”

2. Brooklyn’s Role in Hip Hop Greatness

• “What is it about Brooklyn?” (07:42): Kane credits the “quality of uniqueness” and an independent way of doing things.
• Kane notes he wasn’t the first mainstream Brooklyn rapper—Houdini was, followed by others like Fat Boys and Jimmy Spicer (08:31–09:04).

3. Lifting Others and the Juice Crew Era

• Mentorship & Giving Back (09:46–11:22):
  • Kane’s career was boosted by Biz Markie after a battle in ‘84. In return, Kane felt compelled to help the next generation.
  • “With everything that Biz did for me… I wanted to try to do that for other artists.”

4. Relationships with Biggie & Tupac

• Kane’s Interactions with Biggie (12:35–14:40):
  • Biggie was a fan, and Kane respected Big’s rapid improvement:
    • “Had he lived, I think he would have probably been the greatest MC ever.” (13:19)
  • On their playful phone conversations: “‘Ah, the real big.’ That’s the first thing we… and we just laugh and whatnot.”
• Tupac Connections (14:47–17:12):
  • Kane recalls inviting Pac and Biggie onstage at Madison Square Garden early in their careers, recalling Bobby Brown doing the same for him.
  • Brief studio collaborations:
    • “We worked together before… I recorded a song called Wherever You Are with Pac. I wrote a song for Hammer called What You Gonna Do For Me? And me, Pac and Hammer… did a song called Too Late Player all in the same night.” (17:18–17:54)

5. Almost Signing with Death Row East

• Suge Knight Negotiations (17:54–19:07):
  • Kane recounts Suge offering more than Kane asked for (“I would be insulting you to give you less than a million.”), but Kane declined a $100k upfront, wary of feeling “indebted”:
    • “All of a sudden, that just felt like a gangster move.” (19:07)

6. Reflections on Tupac’s Legacy

• Pac’s Influence & Mythology (22:47–23:40):
  • “Pac would have probably been the Michael Jackson of hip hop.”
  • “Anytime you pass away and people have sightings of you, that’s when you a bad dude.”
• Pac’s Complexity (23:56–25:39):
  • Was Pac authentic? “I think Pac was a real dude. I think… he was just easily influenced.”
• The Reality of Youthful Mistakes: Kane admits they all did “dumb shit” like fighting at afterparties:
  • “You can’t just put that on Pac… we all did that.” (25:31)

7. Money, Success, and Perspective

• Financial Wisdom (28:45–31:20):
  • Kane stresses protecting and wisely spending money, and recognizing those who came before:
    • “There was always someone before you… There was Run DMC before me; Melly Mel before me.”
  • On Drake and Jay-Z’s huge successes:
    • “I love hearing those stories because I know how difficult… especially with Jay Z. Because this is someone who I tried to get a deal for in the early 90s… So to see this dude become a billionaire, I’m like: in their face!” (30:39)

8. The Evolution of Hip Hop: Culture and Genre

• Hip Hop as a Genre (31:33–33:28):
  • Kane explains how hip hop went from marginalized to a global genre. He’s accepting of changing structures, like ghostwriters, observing:
    • “Artists today… are looking at themselves as artists, not as MCs. So it’s different to them.”
• Changing Definitions: "Freestyle" & Biting (34:00–35:29):
  • “What we called biting, today they call paying homage… what we called a freestyle in the 70s and 80s, today they call it a written rhyme.”
  • “Freestyle is free of style, right? You’re not talking about no specific subject matter.” (35:20)

9. Lyricism Then and Now

• Where Are the Lyricists? (35:42–36:25):
  • Kane lists modern lyricists he rates: “Kendrick Lamar… J. Cole… Conway the Machine, Benny the Butcher, Lady London.”
  • “J. Cole is my favorite of this era.” (36:15)

10. Streaming, Ownership, and Sampling

• Kane on Streaming (36:53–37:32):
  • Kane sympathizes with new artists struggling to make living from streams versus hard sales.
• Ownership & Sampling (38:41–41:45):
  • Kane does not yet own his catalog—hopes to soon (“Allah willing.”).
  • On sampling: “I think I would probably rather not hear it… If this is an opportunity for you to shine and become successful, I’d rather you just do you.”
  • On hip hop’s origins: “Hip hop didn’t invent anything. It reinvented everything.” —quoting Grandmaster Caz.

11. Craft and Collaborative Mindset

• Studio Process & Writing (44:42–46:44):
  • Kane likens himself to an artist, painting verses patiently:
    • “I love to think of myself as an artist… I like to take my time and paint a portrait just right.”
• Approach to Collabs (47:07–47:56):
  • “If you… spread love, then I want you to shine. But if you say ‘Kane, I need you to be spitting hard’… Now I’m gonna eat you up.”

12. Old School Competition, Beef, and Respect

• Competitive Spirit in Old School Hip Hop (48:34–52:49):
  • Label focus shifted from party tracks to lyricists after 1986 (thanks to Rakim, KRS-ONE).
  • Rivalries (Juice Crew vs. Boogie Down Productions, LL Cool J vs. Kool Moe Dee, Jay-Z vs. Nas, etc.) were common and “very, very competitive” but rarely personal:
    • “It was love… it wasn’t no real beef. It was like, I got to have it tonight.”

13. Collaborations with Musical Greats

• Working with Quincy Jones (52:49–54:59):
  • Kane describes Quincy’s deep mentorship:
    • “He’s giving me direction as a hip hop artist how to rhyme on a jazz record. That’s how bad he was.”
    • “I think that real music fans know the importance of him.”

14. Star Encounters and Relationship Building

• Being Starstruck (55:09–55:52):
  • Meeting Barry White at a Quincy Jones cookout was a major “starstruck” moment.
• Determining Collaborations (56:01–56:42):
  • Kane says “no” if the direction doesn’t fit or he can’t see himself on the record.
• Meeting Old Dirty Bastard & Wu Tang Clan (58:09–59:02):
  • Kane recalls instantly bonding with ODB and Shaheem after a Wu Tang show.

15. Kane on Modern and Old-School Artists He Loves

• Music Preferences (80:43–81:16):
  • Rides to Willie Hutch and David Ruffin, but at home listens to Lady London, Conway the Machine, and Tyler, the Creator.
• Critiquing vs. Enjoying Music (81:20–82:05):
  • Kane can’t help critiquing new artists, often hoping to give feedback.
• Who Kane Wants to Collab With Now (82:22–83:35):
  • J. Cole, Lady London, CeeLo Green, and Anthony Hamilton.

16. Soul, R&B, and Musical Lineage

• Soul’s Place Today (83:43–85:48):
  • Kane laments the decline of mainstream soul singers, but notes there are still real artists—you just “have to search for them.”

17. The Big Three, Rap Battles, and Hip Hop Competition

• On Rap Beefs Then vs. Now (86:33–88:38):
  • Kane says if someone calls him out, he's responding—“You goddamn right.”
  • On recent battles (Kendrick vs. Drake, J. Cole’s withdrawal):
    • “As I watched the Drake and Kendrick battle unfold, I had so much respect for Cole’s decision… I don’t think the fans were enjoying the battle. I think the fans were trying to fact-check… Just enjoy the battle.”

Notable Quotes & Memorable Moments

• On Mentoring:
  “Each one teach one and someone gave you an opportunity. So now, naturally, you feel it’s Kane’s job to give back. Like somebody gave to me.” —Shannon Sharpe (11:04)
• On Pac’s Influence:
  “Anytime you pass away and people have sightings of you, that’s when you a bad dude.” —Big Daddy Kane (23:09)
• On Suge Knight’s Offer:
  “All of a sudden, that just felt like a gangster move.” —Big Daddy Kane (19:07)
• On Old School Competition:
  “It was love. It wasn’t no real beef, right? It was like, I got to have it tonight, right?” —Big Daddy Kane (52:39)
• On Freestyle vs. Today:
  “What they call freestyle now is what we called off the dome back in the days.” —Big Daddy Kane (35:34)
• On Ownership and Hip Hop’s Nature:
  “Hip hop didn’t invent anything. It reinvented everything.” —Grandmaster Caz, quoted by Kane (41:24)
• On Craft:
  “I love to think of myself as an artist. Like, I’m painting, so…it has to have a meaning.” —Big Daddy Kane (46:08)
• On Legacy:
  “I believe that the Big Daddy Kane legacy will be here when I’m long gone.” —Big Daddy Kane (78:19)
• On Sampling:
  “If this is an opportunity for you to shine…and become successful, I’d rather, you know, you just do you.” —Big Daddy Kane (40:31)
• On Changing Rap Battles:
  “I don’t feel like the fans were enjoying the battle. I think the fans were taking too much time trying to fact-check what they’re saying…Just enjoy the battle.” —Big Daddy Kane (87:18)

Key Timestamps for Important Segments

• Big Daddy Kane’s Background & Brooklyn’s Influence: 04:27–08:00
• Mentorship and Juice Crew Origins: 09:46–11:22
• Reflections on Biggie and Tupac: 12:35–17:54
• Almost Signing with Death Row/East/Declining Suge’s Offer: 17:54–19:07
• Pac’s Legacy, Complexity & Youthful Mistakes: 22:47–25:39
• Success, Money, and Jay Z’s Rise: 28:45–31:20
• Evolution of Hip Hop & Creative Authorship: 31:33–33:28
• Definition War: “Freestyle” Then and Now: 34:00–35:29
• Naming Current Lyricists & Their Place: 36:01–36:25
• Sampling, Catalog Ownership, and Hip Hop’s Roots: 38:41–41:45
• Creative Process & Collaboration in the Studio: 44:42–47:56
• Historical Hip Hop Beef & Competition: 48:34–52:49
• Working with Quincy Jones: 52:49–54:59
• Soul, R&B, and Misunderstood Legacy: 83:43–85:48
• Modern Rap Beefs & Cole/Kendrick/Drake: 86:33–88:38

Closing Thoughts

This episode is a must-listen for anyone fascinated by hip hop’s history and mechanics. Big Daddy Kane’s humility, fierce artistry, and respect for tradition shine through, as does his adaptability to evolving cultural shifts. The episode is rich with anecdotes, advice, and the type of storytelling you can only get from those who lived it.