[ENCORE EPISODE] Ashley Cleveland: Get to Know My Dear Friend episode artwork

EPISODE · Dec 30, 2025 · 1H

[ENCORE EPISODE] Ashley Cleveland: Get to Know My Dear Friend

from The Pivot · host Andrew Osenga

This episode with Ashley Cleveland came out in January 2018—the first time Andrew ever met Ashley. This interview had such a profound impact on Andrew that he’s referenced it again and again throughout the years, and we wanted to re-share it with you as we look to a New Year.  Thought-Provoking Quotes: “I quickly became an alcoholic and a drug addict, but I also became a musician. I started getting a positive response, whereas everything prior had been pretty negative. So I look upon it as this marker that God gave me to keep me on the planet.” - Ashley Cleveland“I knew less than anything about the industry. But a divide had been crossed, and suddenly I’m a songwriter. I dropped out of school after a couple of years and I went back to California and that’s really where I learned to be an artist. I cut my teeth in clubs.” - Ashley Cleveland“I wound up pregnant, very ill with my addiction, so I turned to the church. And I have to say the church responded deeply and wonderfully.” - Ashley Cleveland “I couldn’t even cope with myself, let alone a child. And yet once I heard that heartbeat, I knew it was gonna be beyond me to give her up. Suddenly, there was someone else, and that was really the beginning of faith for me.” - Ashley Cleveland“I left that hospital knowing that there was a God and He loved me, though I had no earthly idea why.” - Ashley Cleveland“You take the art wherever you go. I’m so glad I had a career with a small C because what that meant for me in practical terms was I was home.” - Ashley Cleveland“For me, the best way to live is with my hands wide open and say, ‘Lord, you are the most surprising thing in my life.’” - Ashley Cleveland“I’m so thankful to be alive. Everything else is gravy.” - Ashley Cleveland Links, Products, and Resources Mentioned:Anchor HymnsSally Lloyd-JonesNeil YoungUniversity of TennesseePam TillisJohn HiattNACA (National Association of Campus Activities)Michael W. SmithSteven Curtis ChapmanRich MullinsTwenty Feet From StardomC.S. Lewis *Watch this interview on Andrew’s YouTube channel!  *All episode music is by Andrew Osenga.  Guest’s Links: Ashley Cleveland’s InstagramAshley Cleveland’s Facebook Connect with Andrew: WebsiteYouTubeSubstackSpotifyFacebookInstagramHow to Remember by Andrew OsengaHold the Light by Andrew Osenga *The Pivot is produced in conjunction with Four Eyes Media.

Episode metadata supplied by the publisher feed · Published Dec 30, 2025

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[ENCORE EPISODE] Ashley Cleveland: Get to Know My Dear Friend

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