- Trained in 1984 at Fresno Missionary Baptist Institute for the Ministry.
- Was recognized in 1995 as Top Sales Associate on the Macy's national network.Kerry was awarded for being the 7th top producer in the entire Macy's corporation in 1995.
- His mother, Ethel, raised Kerry and his four siblings by herself with much love. At the age of seven, he remembers the family being down to one old cast iron pot of beans, which had to last for three days. Kerry has a fond memory of his Mom dishing out beans to all the kids and yet not having enough for herself. It was this and his faith in Jesus Christ that brought him to his current success.
- Met his father, Luther Lovelle Pruitt, for the first time in 1982. The Pruitt family moved from Oklahoma during the Great Depression. Coming from a hard life and difficult childhood, Luther raised a family of four successfully.
- His great great grandfather was a Texas Ranger.
- His maternal great great grandfather, William Wood, was a Baptist evangelist, who left the calling to become an actor.
- While performing in 'Murder by Night', he developed a crush for writer and director, Carole Kean. She helped him to grow as an actor and a human being. Her death came as a shock, yet he will always remember her as a fabulous person and actress.
- While doing community theater in Fresno, he became friends with French actor, Alexis Cremieux. The both of them rented a u-haul and moved to Los Angeles in 1991.
- Mitzi Shore of 'The Comedy Store', in West Hollywood, selected Kerry to perform in "Dante's Comic Show", in the Belly Room.
- Is a hardcore believer in Jesus Christ and a member of Victory Baptist Church Burbank CA.
- Considers American Actor, Ryan 'Daniels' Trambley, to be the best roommate ever.
- Kerry is the nephew of Gladys Brashears, owner of the famously haunted, Wolfe Manor, in Clovis California. In 1942, Great Aunt Gladys was considered one of the wealthiest women in Fresno CA. Great Aunt Gladys owned and operated the Clovis Sanitorium, a mental hospital, for over forty years.
- "Murder by Night" was Kerry's first paid acting job. This was the kick start in meeting his theatrical agent.
- To better his relationships, Kerry sought counseling from child psychologist, David Swanson ( son-in-law of music conductor Bill Conti.). David helped Kerry through two most difficult times. The death of his acting mentor, Carole Kean, and the sudden death of his best friend and mom, Ethel Stokes. For this, he is forever grateful.
- Luther 'Junior' Pruitt presented his son, Kerry, with a new car on the first Christmas of their meeting for the first time in 1982.
- Worked with actor and director, Damian Chapa.
- Kerry met his paternal grandmother, Opal, in 1976 while shopping for school clothes in Montgomery Wards, Fresno CA.
- To support the family, Kerry's stepfather, Ron Silvey, drove an ice cream truck in 1967.
- Kerry's maternal grandma, Jesse Violet Schneider, suffered from severe depression. Grandma lost a baby through a miscarriage when she was younger. She spent some time during the 1950s in the Stockton State Hospital. To snap out of her sadness, Grandma Jesse would listen to Elvis Presley singing,"Amazing Grace". This and being surrounded by her grandchildren brought laughter and joy to her heart.
- Kerry was born with a serious heart condition and had to be constantly watched by doctors until he was five. His mom, Ethel, would fall asleep with her ear on his chest listening and prepared to rush to the hospital. Because of her care, he is a happy and healthy adult.
- Kerry's grandfather, Elmer'Tiny' Stokes, is mentioned in Charley Pride's auto biography.
- Kerry's live-in babysitter , 'Crazy Charlie' was a loyal member of a biker gang called 'Lucifer's Knights'.
- Kerry's paternal grandmother Opal was half Cherokee Indian. It was widely known that Grandma Opal carried a gun in her purse.
- Kerry's Grandfather, Elmer'Tiny'Stokes, gave country singer, Charley Pride, his first big break by featuring Charley on Elmer's radio show in Helena, Montana.
- Kerry went to Clovis West High School with classmate, Stand-Up-Comic,Tere Joyce, in Clovis CA, across the street from Clovis Sanitorium (Wolfe Manor).
- To impress his mom, Ethel, and father,Junior Pruitt, Kerry learned to play several classical piano pieces, with selections from Beethoven, Bach, and Brahms, also including Pachelbel's Canon in D Major. While at Fresno Missionary Baptist Seminary, he rehearsed in between classes and before chapel hour.
- Worked with Tony Award winning actress, Christine Baranski, on 'Cybil'.
- Had a near death occurrence in 1971 when his mom, Ethel, while driving down a steep mountain in Auberry CA, realized the breaks had given out. While the kids said a prayer, mom carefully eased the 1957 Ford station wagon down a ravine. All survived.
- In 1970, Kerry's mother, Ethel, armed with a baseball bat, fought off a home invader as he was trying to harm a pregnant friend,Linda Cummings, and her own children. Mom sent the oldest son Randy to the back room to protect his brothers and sisters, while she took down the invader, David Cummings.
- When Kerry's mom Ethel passed away, Kerry Winchester cried nonstop for three days. Immediatly after his mom's funeral, Kerry drove back to Encino CA to have an emergency counseling session. Kerry and David talked and shared many happy moments with his mom. After lots of laughter, Kerry and his therapist and friend, cried together.
- Character actor, Earl Boen, and his wife, Carole Kean, helped Kerry in signing on with his theatrical agent.
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