Club Shay Shay - Anthony Hamilton Part 2

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Anthony Hamilton — Grammy Award-winning singer, multiplatinum songwriter, and one of the most soulful voices in modern R&B — joins Shannon Sharpe for a raw, emotional, and Southern conversation about music, manhood, heartbreak, and legacy. From the “born in a pot of collard greens” grit in his voice to the stories behind his biggest records, Anthony breaks down a life built on struggle, faith, and timeless storytelling.

He opens the episode performing “Charlene,” unpacking the real breakup behind it — waiting by the door, balancing ambition and love, and how men often hide behind their careers. Anthony talks about how long a partner should stand beside someone chasing a dream, the struggle of supporting a family with limited means, and why attention, not money, is the real love language.

After performing “Coming From Where I’m From,” he reflects on how growing up without his father pushed him to hustle harder, and how being adopted at 14 changed his life. He shares that his father didn’t return until right before his wedding — a reunion only made possible by his future wife. Shannon brings up viral memes about his music “sounding like walking home from work,” Flau’jae discovering “Charlene,” and Anthony realizing he’d officially become “old school.”

With “Her Heart,” Anthony discusses making mistakes, breaking promises, and how men grow emotionally. He opens up about crying as a man, why vulnerability is strength, and the meaning behind “I Cry.” Then the mood lifts as he performs “Cornbread, Fish & Collard Greens,” reflecting on why men rarely approach women anymore, social media replacing real connection, and the lost art of old-school flirting.

Anthony shares his favorite Southern dishes and his craziest food experiences before revisiting his early break as a background singer for D’Angelo. He performs “How Does It Feel,” shares lessons D’Angelo taught him, and remembers missing his final phone call. He opens up about D’Angelo’s pancreatic cancer, Angie Stone’s passing, their snowstorm sessions, and the heartbreak of their son losing both parents in one year.

Shannon and Anthony dive into Drake — linking in Toronto, studio sessions at The Embassy, and late-night rides in Rolls-Royces. Anthony compares Drake’s home to Prince’s legendary jam sessions, then takes us inside the homes of Nelson Mandela, Will Smith, and Jamie Foxx, plus his private talk with Barack Obama after performing for him.

He breaks down writing Donell Jones’ “U Know What’s Up,” creating “Thug Mansion” with Tupac, winning a Grammy with Al Green, and collaborating with The Roots, Jill Scott, Chris Brown, Jeezy, Rick Ross, Nas, and more. He discusses unreleased songs with John Legend and Ty Dolla $ign, appearing in DaBaby’s video, signing with Jermaine Dupri, and how music has changed in the streaming era.

Anthony reflects on grinding in New York City with just $67, how Nick Cannon bought him his first car, and the struggles artists like Kevin McCall face. He recalls working on American Gangster with Denzel Washington, Empire with Terrence Howard, witnessing a killing at seven, and his barber days — where the “struggle beard” became his signature. He shares the moment Michael Jordan gifted him Jordans and his experience working with Oprah on They Call Me Dad. He closes by reflecting on raising six sons, marrying young, and how dating feels different after marriage.

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