MORGAN: Struggle Jennings On Getting Shot, Surviving Prison, and Carrying a Legendary Name
The Bobby Bones Show
Premiere Networks
4.8 • 9.8K Ratings
🗓️ 1 September 2025
⏱️ 58 minutes
🧾️ Download transcript
Summary
Struggle Jennings has lived a life few could imagine from surviving gunshots, serving time behind bars, and carrying the weight of being the grandson of country music icon Waylon Jennings. In this powerful conversation, he opens up about the turning points that led him from prison cells to packed-out shows, how he rewrote his story through music, and what it means to honor a legendary name while carving his own path.
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Transcript
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| 0:00.0 | This is an IHeart podcast. |
| 0:04.2 | I just normally do straight stand-up, but this is a bit different. |
| 0:08.0 | What do you get when a true crime producer walks into a comedy club? |
| 0:12.2 | Answer, a new podcast called Wisecrack, where a comedian finds himself at the center of a chilling true crime story. |
| 0:18.8 | Does anyone know what show they've come to see? |
| 0:22.1 | It's a story. |
| 0:23.2 | It's about the scariest night of my life. |
| 0:25.3 | This is Wisecrack, available now. |
| 0:29.1 | Listen to Wisecrack on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. |
| 0:34.1 | Go! |
| 0:36.2 | Go! |
| 0:36.3 | Go! get your podcasts. Take this personally with Morgan Heelsman. The incredible stories are continuing. |
| 0:54.7 | I can't wait for you guys to listen to this interview. |
| 0:56.9 | You may have heard of this guy in a whole bunch of different ways. |
| 0:59.1 | Maybe you listen to one of his rap albums or maybe his country albums or you followed along with him on social media or maybe from his famous grandfather. |
| 1:07.5 | His name is Struggle Jennings. |
| 1:09.9 | He has a story full of resilience and he's being open |
| 1:12.3 | and vulnerable about so many things that have happened in his life. It's one of my favorite |
| 1:16.0 | interviews to date. So without further ado, let's get into it. Morgan here, I'm joined by Struggle Jennings. And I'm really excited because Struggle and I met, gosh, three or so years ago, we played in the Folds of Honor Celebrity Softball game. So Struggle, thanks for joining me. This is awesome. Thanks for having me. I got to carry that trophy home that day. You did. I was supposed to give it to jelly and he never picked it up. So it is on my mantle. |
| 1:45.3 | I love that. |
| 1:46.9 | You're like, by way, it's just mine now. My first introduction to you was you pulled out a whole bunch of snacks out of a backpack. And I was like, I like this guy. Yeah. The dude. I knew it was going to be hot and I was going to have a lot of friends. And I just bring snacks for friends. You knew how to make friends. |
| 1:41.8 | Like you knew the momentum there. |
... |
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