Brett Eldredge sits down with Bobby for a wide-ranging conversation about this new chapter of his life, including finding love, getting married, and how his perspective has changed along the way. Then Bobby counts down his 10 favorite Brett Eldredge songs, with Brett sharing the stories behind each one. He talks about the hits he still loves performing, the songs that surprised him, forgetting lyrics onstage, jumping out of a plane after his first No. 1, and why he hid “Sunday Drive” for years so no one else would record it. Brett also reflects on the songs he connects with most today, the singles that aren’t necessarily his favorites, his love of Frank Sinatra, and celebrating 10 years of Glow.

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Bobby continues the ’90s country music countdown with 1991  a year where Brooks & Dunn exploded with Brand New Man, Trisha Yearwood broke through with “She’s in Love with the Boy,” and Garth Brooks started rewriting the record books. But the year also had some heavy chapters, from The Judds’ farewell tour to the tragic loss of Dottie West and the plane crash that changed Reba’s life. Bobby also revisits Vince Gill joining the Opry, Tracy Lawrence surviving a shooting before his debut album, and the first number ones that helped launch several major careers. Plus, he takes a few detours into 1991 outside of country music  from Nirvana and Magic Johnson to the World Wide Web, Game Boy, and the pop culture moments that made the year feel unforgettable.

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Bobby kicks off a new year-by-year series counting down the top 10 moments that defined country music in the ’90s, starting with 1990. In this episode, he looks back at Garth, Reba, Alan Jackson, Clint Black, The Highwaymen, The Chicks, Tim McGraw, Lorrie Morgan, Travis Tritt, and more — while also sharing conversations with some of the artists decades later about the songs, albums, and decisions that shaped the year. Plus, Bobby mixes in the movies, TV shows, and pop culture that made 1990 feel like the start of something huge.

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Comedian Mark Normand sits down with Bobby for a wide-ranging conversation about life on the road, becoming a new dad, and why he still approaches comedy like he has something to prove. Mark explains why he doesn’t want to rely on crowd work, how he tests new material even when it means having a rough set, and what he thinks about the constant pressure to feed social media with clips. He also shares the comedians who influenced him most, what criticism still gets under his skin, why he prefers smaller rooms to arenas, and how becoming a dad has changed the way he spends his time at home. Plus, Mark gets into his writing process, going viral, making his own movie, and why he’s still happiest just working out jokes.

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For episode 666, Bobby dives into some of the darkest myths and wildest conspiracy theories in music history. He breaks down the legend of Robert Johnson supposedly selling his soul to the devil at the crossroads, why virtuoso musicians were once accused of being possessed, and how Jimmy Page and Led Zeppelin became tied to satanic rumors. Bobby also gets into the strange theories surrounding “Hotel California,” the infamous “Paul is dead” Beatles conspiracy, backward masking hysteria, and whether there’s really anything sinister behind the 27 Club. Along the way, he separates the stories from what actually happened and looks at why people have always been so quick to connect great music with something darker.

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In honor of Dolly Parton’s passing, Bobby shares his final interview with one of the most beloved and influential country music artists of all time. Dolly reflects on the people who believed in her early, growing up in a full house in East Tennessee, finding her voice through music, and staying true to herself through decades of fame. She also opens up about marriage, legacy, hard work, failure, faith, and why she kept creating with the same energy and humor that made the world love her. This conversation is warm, funny, honest, and deeply Dolly — a chance to hear her in her own words, remembering the life she built, the lessons she carried, and the light she gave to so many.

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Comedian Leanne Morgan sits down with Bobby to talk about the long road from small comedy gigs to selling out arenas and landing her own Netflix series. She shares the advice Jerry Seinfeld gave her about success, what it was like beating Lainey Wilson on Family Feud, and the moment she realized her career had reached a completely different level. Leanne also opens up about 34 years of marriage, raising a family while chasing comedy, going viral later in life, and getting renewed for a second season of her Netflix show. Plus, she reveals her five favorite comedians of all time and reflects on the people who helped shape her sense of humor along the way.

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On this episode of Current Stuff, Bobby and Eddie are joined by Lauren Paley who is the singer behind "Punk Goes Princess" which reimagines iconic 2000s pop-punk and rock anthems with cinematic, Disney-style princess vocals! Lauren joins Bobby to talk about  how a DM to Simple Plan’s Pierre Bouvier turned into an actual collaboration. They also get into Lauren’s life as a mom, singing for her daughter, the world of Blippi, Bluey, Cocomelon, Dancing Fruit and Ms. Rachel, and whether she’d ever take her act on the road for kids. Plus, sings a couple of songs for us!

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Bobby goes In The Weeds with the behind-the-scenes story of a slightly awkward Mumford & Sons interview setup and why Brandon walked away embarrassed. He also gets into the ongoing debate with his agent about cutting his hair, what investing in yourself actually looks like, and why he thinks people need to stop saying they “don’t have time.” Plus, Bobby explains his approach to fighting with strangers online, clears up a recent social media moment where people thought he was being rude to his team, and runs through some of the things he just can’t get behind  including running, big group dinners, group chats, trying on clothes and the beach. He also talks about Stanley getting older, the long process behind writing a kid's book, and why he may write another one with Mike D.

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Singer-songwriter and American Idol winner Chayce Beckham sits down with Bobby for a candid conversation about the road that changed his life. He opens up about the drunk-driving car wreck that happened shortly before American Idol, why he didn’t think he had much of a future at the time, and how getting the call for the show gave him a new direction. Chayce also shares the story of marrying his longtime girlfriend in Las Vegas with an Elvis impersonator, what he’s learned after a year of marriage, and why he decided to take time away from music. Plus, he looks back at the success of “23,” starting over in Nashville after winning Idol, and the next chapter of his career with his new project, Old Fashioned.

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In this episode of In The Weeds, Bobby gets into everything from getting humbled by Pat Monahan of Train to the ridiculous amount of credit card points he’s been sitting on. He talks about the strange requests he gets to connect friends with celebrities, why he thinks everyone in radio should be investing in themselves, and the lengths competitors have gone to figure out how to beat his show. Bobby also shares his thoughts on the current podcast landscape, the hosts he actually enjoys listening to, and one interview habit that drives him crazy. Plus, he opens up about being jealous of his daughter’s nursery, why having her own room hits something deeper from his childhood, and what he really means when he tells the Weedeaters to “stay weedy.”

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