Club Shay Shay – Wale (Part 2)

Date: December 17, 2025
Host: Shannon Sharpe
Guest: Wale

Episode Overview

Main Theme:
Shannon Sharpe welcomes rapper and songwriter Wale back for Part 2 of their interview, diving into Wale’s philosophies on dating, privacy, and respect in relationships, experiences navigating the music industry, evolving hip hop and sneaker culture, generational divides, sneakerhead lore, sports fandom (especially Washington Commanders), money, fame, and his aspirations beyond music.

Wale’s candor, signature wit, and introspective style are on full display as he reflects on lessons from his career, the realities of fame and artistry, cultural unity, and staying true to his roots.

Key Discussion Points

Relationships, Privacy, and Navigating the Industry

• Dating Someone in the Industry

  • Wale explains his flexible stance on dating someone who’s been involved with others in the industry—how much he cares about the person vs. how close he is to her ex, admitting "it varies" (05:00).
  • Quote: “If I like somebody and they bringing joy and peace to me, I gotta let some of that other stuff go. Like the past do be the past for real.” – Wale (08:11)

• Public vs. Private Relationships and Reputation

  • Wale discusses pressures of public relationships and the temptation to keep things private to avoid drama and rumors, especially given his status as “just a rapper” in some circles (09:42–10:42).
  • Quote: “If you love somebody, you want to experience the world with them…As soon as it’s not sacred, that’s when things start to just, like, chipping away.” – Wale (10:01)

Music Industry Insights

• Lessons from Industry Titans

  • Wale shares what he learned from mentors/bosses:
    • Jay-Z: Quiet, always 10 steps ahead, had to get over being starstruck (14:28).
    • Rick Ross: “He will over-deliver for any company he works with, taught me the art of over-delivering.”
    • Dr. Dre: Silent, behind-the-scenes, visionary, more distant than hands-on.
    • Quote: “I wish I was a better businessman. I just be super into the art.” – Wale (15:28)

• Industry Friendships Are Transactional

  • On T-Pain’s viral remarks about industry relationships: "Ain’t nobody really, really rocking with you like that if you can’t do something for him." (13:08–13:40)

• Writing for Other Artists & Regrets

  • Wale reveals he’s ghostwritten for several major artists, and fans would be surprised at some songs he’s penned (27:26).
  • On turning down Ella Mai’s “Boo’d Up” and just missing the mark: “That one is probably the only one.” (26:34)

Artistry & Genre Adaptability

• Being a "Swiss Army Knife"

  • Owing to his upbringing and eclectic musical exposure, Wale prides himself on versatility across genres—"Music is music." (28:29–29:30)
  • Quote: "I can do a song with Jelly Roll. I could do a song with Baby Chief. Music is music." – Wale (28:40)

• Nerves and the Creative Process

  • Wale admits he still gets nervous before interviews and going on stage, viewing nerves as a crucial part of performance (29:32–29:55).

• Collaborating with Jerry Seinfeld

  • The collaboration was “about finding the middle ground” between two vastly different people and philosophies (30:18–31:39).
  • On sample clearance, credits Jerry Seinfeld directly getting NBC approvals—labeling it as "impossible to do," but it happened (31:46–32:25).

Reflections: Money, Fame, and Regret

• Money Lessons & Regrets

  • “Hard to keep. Slippery, man… Money don’t really move me like that. It don’t really move me.” (36:05)
  • Final answer: Never at the expense of his artistry or integrity.

• Dumbest Purchase

  • Buying his father a car, which was then shipped to Nigeria: “I thought that was for you.” (37:05)
  • Most regretful moments: “Couple… outbursts. I would say that, but not really. I mean, I’m here, doing great.” (35:21)

• Fame vs. Fortune

  • “Fame, that’s a four letter word around these parts. Now I don’t need fame, man.” (37:52)
  • "Give me the fortune, keep the fame." (38:07)

Generational Divide & Cultural Unity

• On the Kai Cenat Twitch Incident

  • Wale recounts feeling out of place when his influence wasn’t recognized by a new-gen streamer, triggering wider reflection on generational gaps, mental health, and hip hop’s cultural preservation (40:10–48:05).
  • Quote: “The goal after that was to have a teachable moment…but we couldn’t get a comment from a guy. So shout out to him, though.” – Wale (48:05)

• Black American & African Community Dynamics

  • Dismisses the idea of genuine beef: “My upbringing…that whole thing never existed in my world ever” (49:44–51:59).
  • Advocates unity and calls out divisive narratives—“Black folks make the world go round… it’s all one thing.” (52:00–53:59)

Sneaker & Fashion Culture

• Sneakerhead Origins & Culture Shift

  • Wale’s favorites: Foamposite Max, Jordans (Threes, Aqua Eights, Elevens), SB Dunks (66:06, 66:19, 67:26).
  • On sneaker culture’s decline: Oversaturation, bot resellers, poor design innovation (80:02–80:51).
  • On working with Nike: Upcoming boot/campaign collab, but not hands-on shoe design—“We kinda jogging right now” (79:41).

• Notable Quotes:

  • “Jordan everything” when forced to choose—except “foams over Jordan One for sure.” (78:39–78:44)
  • “Dom Kennedy started that—don’t wear LeBrons to the club.” (81:44)
  • “I skipped school to buy them Space Jams. I remember that day.” (67:08).

Sports Fandom & Hot Takes

• Washington Commanders

  • Open, funny commentary on team struggles, stadium name ideas, franchise prospects (57:23–58:17).
  • “Marion Berry Stadium, he the people’s champ. My vote is for Marion Berry Stadium, man.” (57:49)

• QB/Receiver Analysis

  • On Jaden and Terry McLaurin needing help, sports management, and how generational talent gets overlooked (58:58–59:54).

• On Shador Sanders

  • Wale voices strong support for Shador facing media and fan scrutiny (60:00–62:31).
  • “I get it. He been in front of that light this whole time. He the youngest boy… I’m always gonna root for them.” (60:22–62:17)

Rapid Fire: Sneaker and Sports Picks

• Kyrie vs. KD (sneakers): KD6 “Galaxy joints and the Aunt Pearls,” but calls the Kyrie Nikes the best real hoop shoes (73:27–73:49)
• LeBron vs. Kobe: LeBron for the “sevens, eights, that was a moment.” (74:27–74:33)
• Women’s Signatures: "Riding with Angel (Reese)" but loves her shoes. (74:40)
• Deion vs. Bo vs. Vick shoes: Deion’s Diamond Turf 2s for the lore (75:05)

Memorable Quotes & Moments

• “Hard launch, get the dopamine rush… As soon as it’s not sacred, that’s when things start to just, like, chipping away.” – Wale (10:19)
• “A lot of my friends that I consider friends…it ain’t based off how hot they are at the moment.” – Wale (13:40)
• “Music is music.” – Wale (28:40)
• “If I had one wish, that wouldn’t have happened.” (on Ray J and the show incident, 55:16)
• “We gotta wait. We gotta manifest it to happen… I want something to say. We gonna pray on it every day, though, until it happen.” (On Grammy speech, 82:42)
• “All my life been grinding all my life. Sacrifice, hustle, paid the price…” (87:15) – spontaneous musical outro

Notable Segments and Timestamps

• On Dating in the Industry: 04:07–09:29
• Privacy vs. Public Relationships: 09:30–10:42
• Industry Lessons—Jay Z, Ross, Dre: 14:18–15:53
• Wale's Writing for Others: 27:03–28:29
• Jerry Seinfeld Collab: 30:18–32:25
• Money & Fame: 36:02–38:44
• Kai Cenat/Twitch Generation Divide: 40:10–48:05
• African/Black American Unity: 49:29–53:59
• Ray J and Wale’s Gifted Week Show: 54:00–55:49
• Commanders, Stadium Names, and NFL Fandom: 56:57–59:54
• Sneaker Culture and Rankings: 66:46–81:33
• Manifesting Grammy Win: 82:47–82:56

Conclusion

This episode is a revealing, humorous, yet deeply philosophical look at Wale’s journey—his honest takes on love, legacy, industry politics, fame, and cultural identity—interwoven with sneaker nostalgia, sports banter, and the passion to keep creating and uplifting his roots. Wale’s grounded approach to success and fulfillment, and his ability to reflect on experiences both triumphant and painful, make this a must-listen for fans of hip hop, sports culture, and authentic public figures.

Listen if you want: Stories and lessons from hip hop’s front lines, sneakerhead culture, anthems of personal integrity, and the fun, honest spirit of Wale and Shannon Sharpe.