Little Black Sheep: A Memoir

Ashley Cleveland
David C Cook

Grammy and Dove Award-winning singer-songwriter Ashley Cleveland didn’t want to write her memoir. The thought of writing an entire book was overwhelming, and most of all, “It is not an easy story to tell,” she admits in Little Black Sheep: A Memoir, releasing this month.

But after attending a workshop led by author Lauren Winner and an arts conference sponsored by the literary journal Image, Cleveland gained confidence. Bolstered by the encouragement of publishing professionals, she committed herself to the task.

Cleveland’s memoir doesn’t whitewash her journey. “This is the story of the groundwork that paved the way to my faith,” she writes.

Cleveland’s parents were alcoholics in an unlikely marriage; her father believed he was a homosexual, yet her parents were adamant about keeping up appearances. Eventually they divorced, and Cleveland was shuttled from coast to coast between parents, attending many schools and a few churches. She was bullied, struggled with her weight and felt she didn’t belong anywhere.

As a teen and young adult, Cleveland’s hurt led her to a drug and alcohol addiction, even as she discovered her musical gifting along the way. Though her talent provided opportunities for her to succeed, her destructive lifestyle caused her to bottom out repeatedly. When her family intervened, she entered addiction treatment. Though it helped temporarily, she continued to relapse.

Today Cleveland and husband Kenny Greenberg and their three children live in Nashville. She and Greenberg were longtime friends and played together in her band. After they married, Cleveland finally succumbed to her brokenness, where true recovery began.

“I had learned in treatment that the gateway to recovery was willingness. … I needed the will to be willing, and I began to tell the Lord that if He wanted me to turn my wineglass over to Him, He needed to supply me with the will to do it,” she writes.

When someone at an Alcoholics Anonymous meeting challenged Cleveland to attend 40 meetings in 40 days, she agreed. “And on that ordinary day,” she writes, “I began an extraordinary chapter of my life. I began to recover.”

The final pages of Cleveland’s memoir celebrate how God began to restore the years the locusts have eaten, rebuilding her life and using all of her experiences as a way to bring others hope.