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Episode 208: Angels, Outlaws & The Last Name — From Prison to Purpose w/ Struggle Jennings

The Hitstreak

Release Date: 10/14/2025

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More Episodes

Episode 208 of The Hitstreak, a podcast where we talk about anything and everything!  


This week we are joined by Artist, Songwriter & Advocate, Struggle Jennings!



Episode in a Glance:

Check it out! In this episode of The Hitstreak, I get to engage in a deep conversation with Struggle Jennings, a multifaceted artist and advocate. We discuss the importance of pursuing dreams, the challenges of navigating the music industry as an independent artist, and the influence of family legacy. Struggle shares his personal journey, including his experiences with addiction, recovery, and the impact of his music on others. This episode also highlights the work of Smiles for Recovery and Dollars for a Heart, emphasizing the power of community support and the ripple effect of kindness in transforming lives.



Key Points:

- Always pursue your dreams despite obstacles.

- Navigating the music industry requires resilience and creativity.

- Storytelling in music connects deeply with audiences.

- Community support is vital for recovery and growth.

- Independent artists can thrive without major labels.

- Personal growth is a continuous journey.

- The ripple effect of kindness can transform communities.

- It's never too late to change your life.



About our guest: 

Grandson of the legendary Waylon Jennings, Struggle Jennings has built his own legacy by turning hardship into hope. His journey—from battles with addiction and prison time to becoming a voice of resilience—shows that redemption is always possible. 


Beyond the music, Struggle is dedicated to giving back. Through Smiles For Recovery, he helps restore dignity and confidence by providing dental care and support to those in recovery. He also partners with Dollars With a Heart, an organization fighting hunger and responding to urgent needs. Together, they bring both immediate help and long-term healing to those who need it most. 


Struggle’s mission is simple yet powerful: break stigmas, restore hope, and use his platform to change lives.


Follow and contact:

Instagram: @iamstruggle

strugglejennings.com


**Once the goal of 2.5 million members is met, 1,000 limited-edition T-shirts and the unreleased song will be sent, along with the first 1,000 full dental care awards!**



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