Karey Lee Woolsey, a resilient singer-songwriter from Fort Myers, Florida, has transformed profound personal adversity into a compelling artistic narrative through his independent music career. Following an eleven-year federal prison sentence for a non-violent marijuana charge, during which his debut album A Million Miles Away achieved Billboard Heatseekers success, Woolsey has emerged as a symbol of perseverance and renewal. His latest album, REDEMPTION—released on January 2, 2026—fuses elements of rock, pop, Americana, and country rock into an emotionally charged exploration of survival, faith, and second chances, delivered with a charismatic vocal presence and unyielding optimism. In the ensuing dialogue, Woolsey discusses the evolution of his creative path, the thematic depth of this new work, and his aspirations for the future.
- Your musical journey began under extraordinary constraints, with A Million Miles Away charting on Billboard while you were still incarcerated. How did those experiences shape your approach to songwriting and performance upon your release, particularly in developing a genre-blending style that incorporates rock, pop, and country influences?
Honestly, they do have guitars in prison. They barely make any noise, but it’s enough to write songs. That whole time taught me that the real instrument isn’t even the guitar… it’s your soul. That’s where my songwriting comes from.
- “REDEMPTION” is described as a cinematic tale of survival and rebuilding, drawing from your personal story of overcoming imprisonment. In what ways did you channel specific life events into the album’s lyrical and musical framework to convey themes of grit and inspired renewal?
Prison wasn’t really hard in the way people think if you’re trying to do the right thing, but that first year… I didn’t know if I was gonna make it. Over time the walk got easier, and I turned that whole journey into music. That’s really what Redemption is.
⇒”REDEMPTION” can be purchased at Thekareylee.com
- The album features tracks such as “Vibin With Me,” “Please God,” and “Big Mouth Bitch,” which appear to balance introspection with bold attitude. How did you select and sequence these songs to create a cohesive narrative arc that reflects radical perseverance?
The order of the songs wasn’t as important as the feeling of knowing when it was finished. The last song I wrote was “After All This Time,” and it ended up being the last track. It came from running into an old friend after years and realizing… life just moves fast. The people that never wrote back or reached out … it’s just life. People are busy. After talking to this person they actually said a line to me in that song and didn’t even realize it. That moment made me go, “Yep. This album is done.”
- As a self-produced artist handling vocals, instrumentation, and production on “REDEMPTION,” what technical or creative challenges did you encounter in achieving the album’s raw, emotional sound, and how did they differ from your work on previous releases?
Drums… 100% drums. (laughs) I cannot play drums well at all, so some of it was electronic, and I also worked with a great drummer, Darrell Nutt. Coming home after being gone over a decade was crazy too. I left with a flip phone and came back to a different planet. Music tech changed so much, I felt like a dinosaur.
- Your music has resonated on platforms like TikTok, where your resilience has built a dedicated following. How has this digital engagement influenced the promotional strategy and audience connection for “REDEMPTION,” and what role does social media play in amplifying your message of bravery and life celebration?
TikTok has been the best thing that ever happened for me connecting with fans. I had no clue how many amazing people were on there. I’ve gained almost 60k followers in like five months, and I honestly consider most of them friends. I try to answer everybody. Some days it’s 300–500 messages. It’s unreal seeing that many people put my songs on their playlists.
- Tracks like “Self Control” and “After All This Time” evoke a sense of faith and family amid hardship. Could you elaborate on how these elements of personal philosophy informed the album’s overall tone, distinguishing it from broader trends in contemporary rock and pop?
I just want people to feel like it’s never too late. I hit the Billboard charts from inside prison as an independent artist… and I’m the first one to ever do that. I never gave up. Every minute is another chance to turn your life around. And let’s be honest… everybody loves a redemption story. NEVER GIVE UP. I know that’s sort of cliche, but man… it’s sooooo REAL.
- Having transitioned from wrongful imprisonment to becoming a charting artist, what insights from your journey do you hope listeners take away from “REDEMPTION,” especially those facing their own obstacles?
Gratitude doesn’t even cover it. Eleven years without a real pillow or mattress… then you get out and simple things hit you hard. Ice in a cup. Food you’re not scared of. Feeling loved. Having sex!! Let’s be real…over a decade. YOU TRY IT!! Freedom is priceless, and most people don’t even stop to think about it. I write from a soul that’s finally free. I can talk about the past, but I’ll never relive it… songwriting is kind of like visiting it safely, knowing you made it out.
- Looking forward, with “REDEMPTION” marking a significant milestone in your post-release career, what new musical directions or collaborations are you considering to further explore themes of purpose and second chances?
My influences are all over the place. I’ve always loved Chris Cornell, Jeff Buckley, bands like Def Leppard, REO Speedwagon, Skid Row… and I actually just played with Sebastian Bach, which was insane. Singing with one of your heroes is something you never forget.
- Beyond album releases, do you have plans for live performances, multimedia projects, or advocacy work related to criminal justice reform that build on the momentum of “REDEMPTION” and your personal story?
Right now I’m not ready for a tour. I still have too much to say. I’ve already released four more songs since Redemption just in the last month and they’re all doing amazing. I think once people really hear me out and I know they want me in their hometown, I’ll come see them. For now, expect a LOT more music. The Dad Rock King is here.
