On this episode of the BobbyCast, Bobby talks with singer-songwriter Will Anderson about love, loss, and rebuilding a life in public. Will shares why he’s putting out a book of poems written by his late wife, how he’s preserving her voice on the page, and what navigating dating again has really been like. Bobby and Will also wade into politics—their case for free education and healthcare, the idea of an age limit for the presidency, and whether Bobby would ever actually run for office. Will takes us back to the origin of his band Parachute, the early grind, the breakout, and what it would take for them to get back together. It’s an honest, thoughtful conversation about grief, purpose, creativity—and what comes next.

Check out Will on TikTok HERE and Monday Music Club with Willy J HERE

Get tickets to see Will, a copy of his late wife's book of poems, and more HERE

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On this episode of the BobbyCast, Bobby talks with comedian and creator Danae Hays about some very real moments and the weird parts of going viral. She shares the night she was roofied by a fan, what happened after, and how it changed the way she moves through shows and crowds. They get into her first viral clip that hit 21M views, the show where a fan ended up in handcuffs, and why Bobby swears she’s the best athlete he knows. Danae walks through how a former college shortstop turned content maker landed four ESPN Top 10 plays and what that grind actually looks like, and much more! 

Get Tickets to her 'The First Time' Tour at: danaehays.com

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In this episode of the BobbyCast, Bobby shares behind-the-scenes stories from his life in the music and radio industry. He shares why he has been mad at a country artist for years and whether or not he is justified. He reflects on the cliquey nature of the industry, the value of authentic relationships, and why he’s learned to cut out drama and dishonesty. Then, Bobby sits down with bestselling author Jeff Pearlman to dig into the stories behind his deep-dive on Tupac Shakur. Jeff talks about what he really learned while reporting the book—beyond the headlines and mythology—and why such a massive cultural force could still die broke. He breaks down his reporting playbook too: how you track down, organize, and verify insights from more than 650 interviews, and what surprised him most along the way. You’ll hear how money, management, and momentum collided in Tupac’s final years, the moments that reshaped Jeff’s understanding of who Pac was off-mic, and the practical nuts-and-bolts of building a biography at this scale. 

Pre-Order Only God Can Judge Me: The Many Lives of Tupac Shakur HERE

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Iconic country music singer/songwriter, Clint Black sat down with Bobby for over an hour and dove into his decade before the spotlight—ten years of bar gigs that sharpened his craft and set up the big break. Clint also shares the surreal moment when fans started showing up at his house, and how he balanced gratitude with new boundaries. Clint walks Bobby through the making of “A Better Man,” from the first spark to the line that made it click. He also tells Bobby about his worst onstage injury, falling off a stage and what it taught him about recovery and resilience. Plus: how he met his wife, and what’s actually hard about being famous when the lights go down.

Tickets to Clint's 'Back On The Blacktop' Tour: ClintBlack.com

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Bobbys got a bee in his bonnet this week — and he’s buzzing about everything from Bad Bunny and the Super Bowl to how online bots are quietly shaping what we think and feel. He breaks down the weird world of digital manipulation, why outrage spreads faster than truth, and how to keep your sanity in it all. Then Bobby dives into some baby questions from listeners (Razorback or Sooner?), shares what he and Caitlin are most looking forward to, and explains why they’re keeping some details private. Later, Bobby answers a listener's question about his Mount Rushmore of ’90s songs — from Counting Crows to Weezer — plus a fun debate between Bobby, Eddie and Brandon Ray: would you still pay to see a band live without all of their original members?

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On this episode of the BobbyCast, Bobby sits down with music icon, Lionel Richie at the State Theater in Austin, Texas to have a one-hour candid conversation about Lionel's new memoir titled 'Truly'.  Lionel opens up like never before — taking us from his childhood in Tuskegee, Alabama, to the global stages that made him a household name. He shares how his grandmother’s wisdom shaped his outlook on life, the humor that helped him navigate the Jim Crow South, and the moment music truly became his purpose. Lionel looks back on the Commodores forming while in college, what it was like opening for the Jackson Five, and the stories behind timeless hits like “Hello,” “Lady,” and “All Night Long.” He also reflects on the magic of “We Are the World,” the sacrifices behind success, and why family still anchors everything he does.It’s a warm, inspiring conversation filled with laughter, lessons, and a few unforgettable stories from one of music’s most enduring legends.

Check out Lionel's memoir titled Truly HERE: He tells stories about his early life in Tuskegee, Alabama, being super shy as a kid, joining The Commodores, struggles, loss, faith and more. 

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On this episode of the BobbyCast, Bobby sits down with 1985 college football national champion, 2x Butkus Award winner and 2015 College Football Hall of Fame inductee, former Oklahoma linebacker, Brian Bosworth. Bobby asked The Boz if he ever realized how famous he was while playing at Oklahoma. The Boz told the story about the time his team was playing against Washington in a bowl game and the players from Washington were asking him for pictures, and that is when he realized how famous he was. The Boz also talked about his grandad being the reason he chose to go to Oklahoma after he told him he could only go to those games. Bobby asked him what the inspiration behind his infamous haircut was, and The Boz said it was all in spite of his father, who would never let him get anything other than a $7 bowl cut while in high school. Plus, Bobby told The Boz how he found inspiration in a marketing technique he used to create more haters while playing, and much more!
Check him out on Cameo: www.Cameo.com/BrianBosworth 

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On this episode of the BobbyCast, Bobby sits down with finance expert and CEO of Ramsey Solutions, Dave Ramsey. He shares his story of being $3 million in debt, filing for bankruptcy, and why his marriage was hanging by a thread. Dave shared his rule why he never offers to give listeners money and if he carries cash on him. Dave shares why mostly everything on TikTok is WRONG. He also talked about his coolest friend that is famous, why NFL players and professional athletes continue to go broke, and much more!

 Check out: RamseySolutions.com

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On this episode of the BobbyCast, Bobby sits down with one of his closest friends, singer/songwriter, Brett Eldredge. Brett and Bobby open things up by talking about his anxiety when performing and being on stage. Brett talks about the period in his career when he dealt with dysphonia, which is an obsession with how he was projecting his voice, and he had trouble going from song to song. The guys also talked about the reason Brett doesn't do as many live shows these days, the origin story of his Christmas show 'Glow' and how it became a tradition.  

Get tickets to Brett's Glow Tour HERE!

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On this episode of the BobbyCast, Bobby sits down with singer/songwriter, Colbie Caillat. Colbie is best-known for her huge hit "Bubbly". Colbie told Bobby that she never wanted the opening line of "can you count me in" kept in the final cut of that song, but she was ultimately outvoted. Colbie also talks about meeting her music heroes, how she wasn't ready for fame at such a young age, and why social anxiety and being an introvert has led her to hate going on tour. She also tells Bobby that he was cold to her when she first got to his house, so she thought he may not like her, but Bobby tells her that it is actually the complete opposite. 

Colbie's new duets album 'This Time Around' comes out September 26th.Also get tickets to her Christmas Tour with Gavin Degraw at ColbieCaillat.com

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