Bobby’s ’90s country countdown rolls into 1992, a year where Billy Ray Cyrus turned “Achy Breaky Heart” into a full-on phenomenon, Garth Brooks kept dominating everything, and George Strait took country to the big screen with Pure Country. Bobby also gets into major albums from Mary Chapin Carpenter, Vince Gill, Joe Diffie, Randy Travis, and Wynonna, plus Alan Jackson’s run of number ones, Johnny Cash joining the Rock & Roll Hall of Fame, and big Opry moments for Travis Tritt and Marty Stuart. Along the way, he shares past conversations with artists like Billy Ray, Joe Diffie, Randy Travis, and more  while also looking back at The Real World, the Dream Team, the Los Angeles riots, and the parts of 1992 that stretched far beyond country music.

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Bobby talks about what burglars look for when they break into your house, and Amy shares the story of when her home was burglarized, including the part that freaked her out the most. Bobby also has the Top 10 ’90s Country Artists of All-Time, and we battle to see who can name them all. Plus, we play a game where we’re given fictional businesses from TV shows and have to name the show. We also debate whether guys should be wearing their wedding rings at the gym.

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Lunchbox got a lesson in how to make money from a very unlikely source but isn't sure the guy knows what he is talking about. Who wants an easy way to make $50,000 to $60,000 and all you have to do is get some Olympics tickets? Plus Lunchbox almost gets taken out at the golf course and meets someone that 100% lied about what they do for a living. Also Ray has nightmares about the time he tried to sell his season tickets to the Cubs and the Cubs were the worst team in the league which cost him a lot of money. 

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Bobby’s ’90s country countdown rolls into 1992, a year where Billy Ray Cyrus turned “Achy Breaky Heart” into a full-on phenomenon, Garth Brooks kept dominating everything, and George Strait took country to the big screen with Pure Country. Bobby also gets into major albums from Mary Chapin Carpenter, Vince Gill, Joe Diffie, Randy Travis, and Wynonna, plus Alan Jackson’s run of number ones, Johnny Cash joining the Rock & Roll Hall of Fame, and big Opry moments for Travis Tritt and Marty Stuart. Along the way, he shares past conversations with artists like Billy Ray, Joe Diffie, Randy Travis, and more  while also looking back at The Real World, the Dream Team, the Los Angeles riots, and the parts of 1992 that stretched far beyond country music.

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Amy asks a deceptively simple question: “What is something I do that you genuinely do not understand?” That sends the show into a full-on roast session. We try to figure out why Bobby doesn’t enjoy life, why Amy is so scatterbrained, why Lunchbox is so cheap and what everyone does that makes absolutely no sense to the rest of us.

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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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Lauren Alaina joins us on the release day of her first new album in five years. She talks about songs that are tough to sing live, the pressure to hit every note and the emotional story behind a song connected to her late father. Plus, we finally get the REAL story behind the time Lunchbox apparently creeped out a country artist. And we kick off September with a round of Famous Firsts Trivia!

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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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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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