Club Shay Shay – Anthony Hamilton Part 1

Host: Shannon Sharpe
Guest: Anthony Hamilton
Release Date: November 12, 2025

Episode Overview

In this soulful and candid episode, NFL legend Shannon Sharpe sits down with Grammy-winning R&B artist Anthony Hamilton for a unique blend of live performances and deep conversation. The episode weaves together Hamilton’s most iconic songs with honest discussions about heartbreak, work-life balance, family, forgiveness, and staying authentic in the music industry. Hamilton’s journey from North Carolina to international stardom is on full display, as both men reflect on the sacrifices made in pursuit of greatness and the enduring power of R&B.

Performance & Conversation Structure

• Anthony Hamilton performs several hit songs live, each followed by a reflective conversation with Shannon Sharpe about the story and emotion behind the music.
• Topics range from personal struggles, fatherhood, forgiveness, music industry realities, and the evolution of R&B.
• The tone is heartfelt, humorous, and at times, deeply vulnerable.

Key Discussion Points and Insights

1. The Story Behind “Charlene”

Performance: [05:16]
Discussion: [08:51 – 13:00]

• Hamilton reveals “Charlene” is based on a real relationship, though the name was changed to protect privacy.
• He discusses the challenge of sacrificing personal relationships for a career in music:

  “Sometimes it’s not good enough to be successful in your business, and home suffers. So a series of events happened. We broke up, and, you know, heartbreak created a song, a staple song for me.” — Anthony Hamilton [09:20]

• Sharpe notes the difficulty of finding balance outside of a traditional 9-to-5:

  “Work, life balance is 9 to 5. But when you trying to get it like you were trying to get it, there is no balance.” — Shannon Sharpe [09:55]

• Both reflect on how partners and children make sacrifices that the world doesn’t always see.

2. Work-Life Sacrifice and Parenthood

[13:01 – 16:37]

• Hamilton discusses being a father to six sons, and how his older boys felt the brunt of his demanding schedule.
• He tries “to go harder now for my last three.”
• Both men reflect on the guilt and trade-offs that come with chasing dreams:

  “My ex wife had to come pick [my kids] up last night because I, you know, I had to be here…To do this. I ain't gonna miss the club. I'm gonna miss it again.” — Anthony Hamilton [13:45]

3. Endurance in the Face of Industry Setbacks

[16:37 – 18:53]

• Hamilton details a ten-year journey from his first record deal in 1993 to mainstream success in 2003.
• He almost gave up after repeated disappointments but was sustained by small wins:

  “God gave me something…little things to keep me going. Yeah. It's like, nah, I got something better for you, so just stay the course.” — Anthony Hamilton [17:45]

• Humorous take on hustling as a barber to make ends meet during tough years:

  “The haircut’s $10, right? You got 450 and a nickel bag. That ain’t gonna work.” — Anthony Hamilton [18:53]

4. “Coming Where I’m From” – Roots, Pain, and Resilience

Performance: [23:32]
Discussion: [26:32 – 31:39]

• “Coming Where I’m From” draws on personal childhood adversity: parental absence, adoption, striving for identity.
• Hamilton shares how pain and instability shaped his grit:

  “That unstable situation in my life…it made me work harder. It put a little pain in there, a little grit. I probably would’ve sounded like Barry Manilow had that not happened.” — Anthony Hamilton [27:46]

• His relationship with his father was strained, but they reconciled before his father’s passing thanks to a push from Hamilton’s then-wife.

5. Family, Reconciliation, and Loss

[31:40 – 35:23]

• Hamilton recalls healing old wounds with both parents, finding forgiveness as his mother was dying and after reconnecting with his father.
• On letting go of resentment:

  “Life is…Was it hard to let it go? Yes. Because sometimes people hold on to things…You sometimes you got to learn from somebody else's mistake.” — Anthony Hamilton [34:32]

• Discovery of additional siblings at his father's funeral underscored the complexities of family:

  “It’s hard meeting somebody in your 50s, and they’re like, ‘Oh, I’m your brother.’” — Anthony Hamilton [33:18]

6. The Evolution and Integrity of R&B

[35:49 – 39:04]

• Hamilton weighs in on the claim that R&B is “dead”:

  “I ain’t never been to no funeral…The core of R and B and the core soul music, it's in every rap song you ever heard, every country song, every church record. I don't think it’ll ever go anywhere.” — Anthony Hamilton [36:29]

• He bridges the gap with younger artists via collaborations, noting his unique sound can’t be sampled without coming to him first:

  “Certain voices you can’t duplicate. If you want that sound, you got to come to me.” — Anthony Hamilton [38:49]

7. Songwriting and Personal Growth (Her Heart)

Performance: [41:15]
Discussion: [49:18 – 54:21]

• “Her Heart” is about repeated mistakes in love and genuine remorse. Hamilton admits to “bowlegged” living but recognizes maturity is uneven:

  “Maturity in different areas of your life come at different times. When you’re not sure of who you are, you don’t know how to be the best version of yourself.” — Anthony Hamilton [51:08]

• Reflections on vulnerability, male emotional expression, and why men are reluctant to cry:

  “I think it’s a sign of freedom. If you free, you can express yourself. Whether you’re weak for a moment, that’s fine.” — Anthony Hamilton [56:33]

8. Community, Upbringing, and Soul Food

[58:03 – 76:17]

• Hamilton and Sharpe reminisce about community discipline and how today’s youth miss out on collective guidance.
• The importance of food and family in North Carolina:

  “Cornbread, it’s the foundation…solid…Collard greens, keep things clean around there. And that fish, you learn how to move right.” — Anthony Hamilton [61:24]

• Hilarious exchanges about Sunday dinner, favorite Southern dishes, and culinary traditions (“You want it fried…come right about the grease.” — Shannon Sharpe [73:22])
• Hamilton explains he stopped eating red meat, pursued veganism, and now seeks balance in diet and life.

9. Music Journey: From Backup Singer to Leading Man

[76:17 – 86:11]

• Hamilton’s stint as a backup singer for D’Angelo was transformative:

  “I didn’t go to a four-year college, but I felt like that was a university that you couldn’t even pay to get in…For me to learn what true musicianship is.” — Anthony Hamilton [76:35]

• He put aside ego to “learn how to lead from learning how to follow.”
• The episode closes with a tribute to D’Angelo—Hamilton recounts his personal connection, the regret of missing D’Angelo’s last phone call, and meditations on loss.

10. Men’s Health & Early Detection

[86:42 – 89:32]

• The gravity of health concerns in the Black community is addressed, especially regarding cancer screenings.
• Both share their journeys in getting tested and encourage listeners to prioritize health.

  “If you catch something early enough, there's a chance you can beat it…We got a better chance.” — Anthony Hamilton [87:04] “I was called prostate cancer early… I started getting tested at 35.” — Shannon Sharpe [87:22]

Notable Quotes & Memorable Moments

• On love and sacrifice:
  “Sometimes it’s not good enough to be successful in your business, and home suffers. So a series of events happened. We broke up, and, you know, heartbreak created a song, a staple song for me.” — Anthony Hamilton [09:20]

• On pain and artistry:
  “I probably would’ve sounded a little bit like Barry Manilow had that not happened.” — Anthony Hamilton [27:55] (on his tough upbringing)

• On bridging generations of R&B:
  “They want to be a part of that soul world, and they know where to come and get it…Certain voices you can’t duplicate.” — Anthony Hamilton [38:49]

• On emotional honesty:
  “I think it’s a sign of freedom. If you free, you can express yourself.” — Anthony Hamilton [56:33] (on men crying)

• On learning from others:
  “A wise man learns from others' mistakes. A fool has to learn from his own.” — Shannon Sharpe [52:42]

• On food and culture:
  “Cornbread, it’s the foundation…Collard greens, keep things clean around there. And that fish, you learn how to move right.” — Anthony Hamilton [61:24]

Selected Timestamps for Key Segments

• “Charlene” Performance: [05:16]
• Behind “Charlene” Meaning: [08:54 – 13:00]
• Industry Struggles & Early Hustle: [16:37 – 18:53]
• “Coming Where I’m From” Performance: [23:32]
• Family & Forgiveness: [31:40 – 35:23]
• R&B's Evolution & Legacy: [35:49 – 39:04]
• “Her Heart” Performance: [41:15]
• Emotional Expression & Masculinity: [49:18 – 56:33]
• Food, Upbringing, & Community: [58:03 – 76:17]
• Backup Singing for D’Angelo: [76:17 – 86:11]
• Men’s Health & Early Detection: [86:42 – 89:32]

Final Thoughts

This episode of Club Shay Shay is a rich, multi-layered conversation propelled by honest dialogue and stirring performances. Anthony Hamilton gives listeners a window into the struggle, artistry, and humanity behind his timeless songs, while Shannon Sharpe’s probing empathy and humor make for a deeply engaging listen. Together, they champion resilience, authentic self-expression, and the importance of roots, both musical and familial.

To continue the conversation, check out Part 2, available now on all podcast platforms.