Oscar Chasteen, Jr., passed away suddenly in the early morning hours of Wednesday, August 6, 2025, at his home in Cawood, Kentucky.

Although he was born in Cincinnati, Ohio on June 18, 1966, to Oscar Sr. and Rita (Jewell) Chasteen, Oscar Jr spent most of his years living in Harlan County. He was an adventurous boy who always enjoyed being outside, whether he was riding his mini-motorcycle or fishing. He was afraid of nothing yet never drew attention to himself. He attended James A. Cawood High School then married his long-time sweetheart, Nettie Middleton, July of 1984. They were blessed with forty-one wonderful years together and two sons whom they adored, Chad and Dylan. Oscar and Nettie shared a deep, abiding love for one another. They found joy in one another's company, supported each other through challenges, and shared a deep connection.

Oscar drove a coal truck for many years before going underground in the mines. He worked hard to provide for his family and was underground for twenty-nine years before retiring.

A quiet, gentle man, Oscar also had a fun-loving side to him. He loved being outdoors, especially in the Fall, when the weather turned cooler and loved fishing with Nettie and his boys every opportunity he could get. He was a wonderful father and was present at every event his boys were involved in. When his granddaughters were born, Oscar became an incredible Papaw.  Amelia and Abigail thought Papaw hung the moon and he felt the same about them. Every morning, Oscar would wake and walk across the yard to take his grandbabies (who lived beside him) breakfast in bed, pack their school lunches, and help get them ready for school. He often invented funny stories and silly songs that he shared with the girls. Whatever his girls were involved in, Papaw was there supporting them.

Oscar's absence leaves a void that can never be filled. He loved big and all who were blessed to know and love him will carry his love and memories all the days of their lives.

Oscar is preceded in death by his parents, Oscar Sr. and Rita; grandparents, Mallie and John Chasteen and Mable and Bill Jewell; and his father-in-law, Bobby Joe Hensley.

Those left to cherish his memory include his wife of forty-one years, Nettie Chasteen of Cawood, KY; two sons, Chad (LeAnn) Chasteen of Cawood, KY and Dylan (Gabrielle) Chasteen of Lexington, KY; two granddaughters, who were the apples of his eye, Amelia and Abigail Chasteen; a sister, Debbie (Don) Hensley of Loyall, KY; nieces and nephews: Shelley Engle, Donovan Hensley, Carley Pack, Cody Pack; mother-in-law, Carlene Hensley; sister-in-law and brother-in-law, Tammy and Tommy Bailey; a host of extended family members; as well as many friends.

In keeping with his family's wishes, there will be no services.

Harlan Funeral Home is honored to serve the family of Oscar Chasteen, Jr.