Charles Webster (Web) Allen, 41, of Jackson, passed away unexpectedly from cardiac arrest on Tuesday, April 1, 2025. Born in Jackson on April 6, 1983, to Hogan Allen and Lynn Webster Fillingham, Web was reared in Madison and Jackson. He attended schools in both areas and later pursued his education at the University of Alaska. Webster had a deep love for the Lord and formed loyal, lasting friendships wherever he went. Web built a successful career in construction and real estate; then developed a deep knowledge of the roofing industry. In 2018, he founded Key Roofing, LLC, turning it into a thriving, highly regarded company serving the Tri-County area. He was especially proud of his company's five-star Google rating, a testament to the dedication and exceptional service he and his co-worker, Michael Neel, strived to achieve. Outside of work, Web had a wide range of interests, including playing guitar, bow hunting, reading, and spending time outdoors with intensive yard work and land clearing. Webster cherished his three nieces-Ella Peyton Allen (19), Braelynn Allen (9), and Mary Parker Allen (6)— through his beloved brother Parker, he always enjoyed their laughter, antics and fun especially at the beach or in the pool. Web was preceded in death by his paternal grandparents, Ben and Ann Allen of Vicksburg, and his maternal grandparents, Sidney Webster of Jackson and Charles R. Webster of Madison. He is survived by his parents, Hogan Allen and Lynn Webster Fillingham, step-father Frank Fillingham, his brother, Benjamin Parker Davies Allen (38), his maternal step-grandmother, Peggy Webster of Madison, aunts and uncles Ben and Susie Allen, Ginger Allen, Kim Allen Powers, Pamela Claypool, Chuck and Caroline Webster, Rick and Ann Webster, his beloved nieces, as well as a host of cousins. Web's infectious laughter, unwavering integrity, and loyal friendships will be deeply missed but never forgotten. His family takes solace in knowing he lived a large full life of love, laughter, and an unshakeable positivity, bringing light to everyone he encountered. A celebration of life will be held at the Natchez Trace Funeral Home, 759 US-51, Madison, MS 39110. Public viewing 12:30 - 1:30pm, Celebration of Life service 1:30-2:30; with family only graveside services to follow.