Henry Matthews was born August 15, 1978 in Belleville to the union of Henry Matthews Sr. and Valerie K. Matthews. Henry confessed a hope in Christ at an early age. Henry was united with Bibleway Deliverance Church in Venice, Illinois.

He graduated from Lincoln High School in 1996 then later attended Southwestern Illinois College. He moved to Granite City in 1999. Henry united in wedlock with his soulmate Casondra Nicole Matthews on August 18, 2001.

Henry worked at World Wide Technology for 6 years. He enjoyed barbecuing, watching football, baseball, and basketball, and spending quality time with his family. He was a handy man around the house. He was a jokester "literally."

Henry departed this life on October 18, 2020. Henry was preceded in death by his maternal and paternal grandparents and also by his brother Armond C. Matthews. He leaves to cherish his memory his wife Casondra Nicole Matthews of Granite City, IL; his son Darione Antione Matthews; daughter Daryia Valerie-Marie Matthews; father Henry Matthews Sr., East St. Louis, IL.; mother Valerie Katheirne Matthews, East St. Louis, IL.; brother Keith Andre Matthews, Fairview Heights; sisters Cheryl Lynn Matthews (Augusta, GA), Dawn Patrice King (Keith), Atlanta, GA, Regan J. Braddick (Anthony), Augusta, GA; uncle Willie Matthews (Saundra), Batesville, Mississippi; great-aunt Valdonia Mayweather, Chicago, IL; sister-in-law Tina Matthews; mother-in-law Linda Spruel; father-in-law James Spruel; and numerous other relatives and friends.