Giancarlo Valencia 5/6/26 Giancarlo Valencia 5/6/26

Chicago Rapper JayWoodSole discusses losing close family dealing with pressure and creating his album “Paradise Don’t Last Forever”

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Giancarlo Valencia 5/6/26 Giancarlo Valencia 5/6/26

ogstevo talks about lessons from toxic relationships, accepting love and moving on

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Giancarlo Valencia 5/6/26 Giancarlo Valencia 5/6/26

Chicago rapper Soski discusses struggles as a child, communication and new album “Soski World”

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Giancarlo Valencia 5/6/26 Giancarlo Valencia 5/6/26

BDO Montanez discusses losing his identity, dance, and creating Brand Face Media

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Sad Boy Radio . 5/6/26 Sad Boy Radio . 5/6/26

Babychiefdoit: The next big thing in Chicago

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Sad Boy Radio . 5/6/26 Sad Boy Radio . 5/6/26

Feid Brings “Feid vs Ferxxo: Falxo Tour” to House of Blues Chicago — A Return to Intimacy

Feid Brings “Feid vs Ferxxo: Falxo Tour” to House of Blues Chicago — A Return to Intimacy

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Sad Boy Radio . 4/29/26 Sad Boy Radio . 4/29/26

Blessd Concert Review: Colombian Star Shuts Down Rosemont Theatre (Chicago)

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Sad Boy Radio . 11/13/25 Sad Boy Radio . 11/13/25

DJ Kid Clay Reflects on Past Mistakes & Growing From Flaws

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Sad Boy Radio . 11/13/25 Sad Boy Radio . 11/13/25

Miguel Barraza Talks Work With Lyrical Lemonade & Representing Latinos

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Sad Boy Radio . 11/13/25 Sad Boy Radio . 11/13/25

daedaePIVOT Talks Finding Himself After Battle With Grief

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Sad Boy Radio . 10/21/25 Sad Boy Radio . 10/21/25

PartyNextDoor “TBH” Song Breakdown

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Sad Boy Radio . 10/21/25 Sad Boy Radio . 10/21/25

Casino Trell Performs “No Solicitors Allowed” Sad Boy Radio Live

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Sad Boy Radio . 10/21/25 Sad Boy Radio . 10/21/25

HXRY Reflects On Pain From Past Relationships

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Sad Boy Radio . 10/21/25 Sad Boy Radio . 10/21/25

Corlie Talks Learning to Forgive & Self-Love

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Sad Boy Radio . 10/21/25 Sad Boy Radio . 10/21/25

Hector De La M Talks Leaving Group Vanguardia & Losing Love for Music

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Sad Boy Radio . 10/21/25 Sad Boy Radio . 10/21/25

SoloCelo Performs “IDOL” Sad Boy Radio LIVE

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Sad Boy Radio . 10/21/25 Sad Boy Radio . 10/21/25

RecoeChi Talks FIRST ALBUM “Flavaz”

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Sad Boy Radio . 10/21/25 Sad Boy Radio . 10/21/25

Flex Sinatra Leaves Def Jam

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Sad Boy Radio . 10/21/25 Sad Boy Radio . 10/21/25

Mike DFG Talks Struggles With Childhood Trauma

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Sad Boy Radio . 10/21/25 Sad Boy Radio . 10/21/25

Drew Harley Talks Music Journey & Working at Interscope Records

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