Club Shay Shay – Anthony Hamilton Part 2
Podcast: Club Shay Shay
Host: Shannon Sharpe (iHeartPodcasts and Shay Shay Media)
Guest: Anthony Hamilton
Date: November 12, 2025
Episode Overview
In this heartfelt and wide-ranging conversation, soul legend Anthony Hamilton joins Shannon Sharpe for the second part of his Club Shay Shay interview. They discuss Hamilton’s musical journey, collaborative spirit, family life, personal struggles, business lessons, and connections with icons from Al Green to President Obama. Hamilton’s candid stories and warmth give insight into the soul behind the music—and the importance of staying true, both as an artist and a father.
Key Discussion Points & Insights
Grief, Angie Stone, and Being There for Friends
[02:41–04:34]
- Hamilton shares the difficulty of singing at Angie Stone’s funeral, recounting facing his fears to view her body and finding peace in her appearance.
- He recalls a cherished memory with Angie: heading out of a New York studio into a blizzard, struggling to find a cab. Their “country” background made the city snowstorm a funny misadventure.
“She had a smirk on her face. Like, I told y’all, I’m serious, man. In all Angie Stone fashion.” —Anthony Hamilton, [03:14]
- On D’Angelo’s losses (mother and father), Hamilton voices empathy and hope for comfort and healing.
Collaboration Across Genres & Risk-Taking
[05:20–07:03]
- Hamilton describes seamless transitions between genres (rap, country, rock), drawing on authentic love and understanding of each.
- He’s currently working on a country album, inspired by his own roots and artists like Beyoncé who risk audience expectations.
“People want to control your destiny and your happiness… No, I know who I want to be, and I know all the many me’s I want to be.” —Anthony Hamilton, [06:42]
Brushing Shoulders with Legends
[07:03–10:54]
- Stories include visiting Prince’s Paisley Park, late-night jam sessions with music royalty, and moments at the White House with President Obama.
- Meeting Nelson Mandela was planned but fell through due to Mandela’s illness. Hamilton met Mandela’s family and felt the leader’s spirit in his home.
“His house… the spirit of who he was, it was permeating throughout that house. It was very strong.” —Anthony Hamilton, [10:00]
Nerves, Artistic Excellence, and Songwriting
[10:54–14:24]
- Hamilton opens up about feeling more pressure singing at award shows, due to the immediate judgment of peers.
- He distinguishes between being a great artist and a great writer; great records can be made regardless of who pens them.
- On writing “You Know What’s Up” for Donell Jones, Hamilton describes writing specifically for an artist versus bringing a unique flavor that pushes boundaries.
- He explains the evolution of songwriting credit splits, from by-the-line negotiations to the modern more collaborative, even distribution.
Behind the Music: Tupac, Song Placement, and Writing for Others
[14:24–16:46]
- Details the process of writing and singing on Tupac’s “Thugz Mansion,” channeling what he believed Pac would want to hear about heaven.
- Hamilton reflects on balancing writing for someone’s style without stifling his originality.
“They called you in for a reason, for you to give them something a little different.” —Anthony Hamilton, [15:45]
Grammy Wins & Working with Al Green
[17:07–22:41]
- Winning a Grammy with the legendary Al Green stands out as a career highlight, most gratifying for the validation it brought his family.
“The moment I said, you know, I’m singing with Al Green… they were like, ‘Oh, baby, I knew you was gonna make it.’” —Anthony Hamilton, [22:25]
Eclectic Collaborations & Dream Pairings
[22:41–27:02]
- Hamilton lists his diverse range of collaborators (The Roots, Nas, Rick Ross, Fantasia, Jill Scott, etc.), emphasizing a desire to create with those “moving the needle.”
- Dream collaborations include Lauryn Hill (“I’ll wait on her. Same outfit, ’cause I picked it out for her.” – [26:36]) and unreleased songs with John Legend, Ty Dolla $ign, and Jacquees.
Family Ties & Early Career
[29:35–32:27]
- Hamilton discusses his familial connections with Jodeci, realizing they were related after both achieved success, and the wild experience of touring with them early in his career.
- Transitioned from opening act to headliner—“I can shut the curtain now.” —Anthony Hamilton, [32:09]
Reflections on Touring & Who's Next
[32:27–34:11]
- Hamilton praises past tours (Maxwell, Joe, Fantasia) and names new acts he admires (such as upcoming singer EJ—“the chosen voice… he sounds like Johnny Taylor.” —Anthony Hamilton, [33:47])
- Expresses admiration for artists like Michelle Ndegeocello and the impact of great venues (Hollywood Bowl, Chastain Park).
Industry Realities: Streaming, Money, and Ownership
[44:00–51:02]
- Candid about the financial drawbacks of streaming for artists. “They trying to kill us… robbing you… you have to spin so many times to get anything worth taking home.” —Anthony Hamilton, [44:08]
- Reminisces about the tactile experience of buying music on vinyl, cassettes, or CDs.
- Opens up about business lessons: greatest purchase was his first home, and he values investments and financial advice over “just having” money.
“If you don’t know how to invest it the right way, then it’s just… sitting there and it’s not really doing a lot.” —Anthony Hamilton, [49:54]
Upbringing, Trauma, and Family
[57:56–73:58]
- Hamilton raises six boys, four of whom live with him most of the time; he’s hands-on as a father, handling school drop-offs, meetings, and tutoring arrangements.
- Describes the challenge of ending a marriage with kids involved and commends the value of both parental presence and healthy relationships.
- Recounts his own fraught upbringing: being adopted at 14 by a family friend, dealing with unresolved anger, and witnessing a traumatic shooting at age seven.
“I just felt like you being a parent, you should know better. You should be able to… do a little different.” —Anthony Hamilton, [72:16]
Staying Humble, Giving Back, and Maintaining Connections
[76:31–79:32]
- Hometown pride in singing for the Charlotte Hornets and support from Michael Jordan.
- His journey from barber school (“I’m good with the clippers!” —[74:36]) to keeping his sons’ hair fresh.
- Parting gifts and shout-outs to up-and-coming talents from Charlotte; emphasis on gratitude and supporting the next generation.
Notable Quotes & Memorable Moments
- “I know what it means, and I know what it should feel like, and I love it. So, you know, it’s just… It’s an extension of who I am. I never feel like I’m out of my character.” —Anthony Hamilton on genre-hopping, [05:50]
- “Do you ever get impressed?... I’m impressed to be right here on the show, Club Shay Shay.” —Anthony Hamilton, [23:41]
- “When you bring writers in, sometimes you get in the studio with people who are greedy… those are the writers you want to stay away from.” —Anthony Hamilton, [12:52]
- On touring with Jodeci: “I thought I wanted to be in the music business… but the amount of women… I was a little nervous… Not ready.” —Anthony Hamilton, [30:31]
- “The more you make, the more somebody need it.” —Anthony Hamilton on wealth, [49:30]
- About parenting: “I want to give you a voice… guide you based on who you are as opposed to making you be who I think you should be.” —Anthony Hamilton, [68:48]
- “I don’t want them to resent me later on when money can’t… fix it.” —Anthony Hamilton, [58:57]
Timestamps for Important Segments
- Singing for Angie Stone’s funeral: [02:41–03:37]
- Crossing genres and future of collaborations: [05:20–06:19]
- Career highlight – working with Al Green: [21:22–22:41]
- Family, divorce, and parenting reflections: [57:56–60:28]
- Business and ownership lessons: [49:30–51:02]
- Music industry and streaming reality: [44:00–45:40]
- Early life trauma and adoption: [71:08–73:32]
- Shout-outs to emerging artists & hometown pride: [78:46–79:47]
Tone & Takeaways
Hamilton’s tone is open, genuine, and warm throughout. There’s plenty of laughter, Southern storytelling, and honest conversations about hardship, legacy, and love for music and family. He’s humble in his reflections, passionate about his craft, and resolutely grounded despite stardom.
For listeners, this episode offers an intimate look at the realities of a soul icon—his struggles, joys, values, and the ongoing grind for greatness and authenticity.