Cleaster was born in Indianola, Mississippi, on August 22nd 1959. He accepted Christ at an early age at Mount Beulah Missionary Baptist church. He graduated from Gentry High School school in 1978.

Cleaster had a passion for music and family. He had many paths and role modeling during his lifetime, such as a cop as well as being in the service. However, most of his time was spent traveling across the United States as a truck driver, where he gave too many..

Cleaster proceeded his parents, Odessa Miles and Glenn Applewhite; and a sister, Joann Applewhite, in death.

Cleaster received his wings to eternal life on Tuesday, March 18, 2025.

He leaves behind many to cherish his life; 2 brothers, Glenn Applewhite Jr and L.C. Applewhite; his wife, Sheila Applewhite; 6 children; Cleaster Shepard, Seth Applewhite, Dominique Brown, Darius Palmer, Stacia Applewhite and Tylar Applewhite; 8 grandchildren; 1 niece; and a host of nephews, relatives and friends