#386 - Hailey Whitters On The Country Stars Who Have Slept On Her Couch + Once Being So Broke She Had To Sleep In The Airport + Funding Her Own Album That Led To Her Breakthrough

#386 - Hailey Whitters On The Country Stars Who Have Slept On Her Couch + Once Being So Broke She Had To Sleep In The Airport + Funding Her Own Album That Led To Her Breakthrough

Hailey Whitters (@HaileyWhitters) first single at country radio "Everything She Ain't" is climbing the charts and she stopped by Bobby's house before going on her new headlining Raised Tour. Hailey moved from a small town in Iowa to Nashville 15 years ago to pursue a career in country music but kept facing struggles. She talks about all the difficulties she had and ways she tried to make it, the jobs she had to take to survive, and the moment she got her publishing deal and first big song recorded by another artist but was still so broke she had to sleep in the airport one night. Hailey shares how she self-funded her 2020 album 'The Dream' that lead to her first breakthrough before getting her record deal. She also talks about the country artists who have slept on her couch and watching them all become successful before she did, and how it feels to finally have a song on radio. Plus cool moments like getting to perform on Jimmy Kimmel and Kelly Clarkson covering her song.

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Episoder(721)

#594 Annie Duke On Quitting & Bobby & Eddie Luckiest Moments in Music History

#594 Annie Duke On Quitting & Bobby & Eddie Luckiest Moments in Music History

Bobby sits down with Annie Duke to talk about luck, skill, decision-making, and why quitting is not always a bad thing. Annie explains how luck plays a bigger role in life than most people want to adm...

9 Apr 1h

#593 - Switchfoot Lead Singer Jon Foreman on Almost Breaking Up Before “Meant to Live” Getting Dropped & Bad Financial Decisions

#593 - Switchfoot Lead Singer Jon Foreman on Almost Breaking Up Before “Meant to Live” Getting Dropped & Bad Financial Decisions

Switchfoot lead singer, Jon Foreman sits down with Bobby to talk about how close the band came to breaking up before “Meant to Live” became the song that changed everything. He opens up about the unce...

7 Apr 1h 3min

Father Knows Less with Bobby Bones: Baby Gifts from Celebrities

Father Knows Less with Bobby Bones: Baby Gifts from Celebrities

Bobby talks about getting baby gifts from celebrities and his wife leaving him with the baby at home. He shares stories about his first stretch alone with the baby and realizes pretty quickly he’d rat...

3 Apr 33min

#592 -  Old Crow Medicine Show’s Ketch Secor and Molly Tuttle on Wagon Wheel

#592 -  Old Crow Medicine Show’s Ketch Secor and Molly Tuttle on Wagon Wheel

Old Crow Medicine Show’s Ketch Secor and Grammy-winning singer-songwriter Molly Tuttle sit down with Bobby to talk about their love story, how their relationship came together, and the moments that ma...

2 Apr 1h 17min

#591 - GMA Host Michael Strahan on Splitting a Bottle with Julia Roberts & Going to Space

#591 - GMA Host Michael Strahan on Splitting a Bottle with Julia Roberts & Going to Space

Michael Strahan sits down with Bobby to talk about why the daily grind of live television ended up being tougher than life in the NFL, and how he made the transition from football star to morning TV h...

31 Mar 45min

#590 - Black Crowes Lead Singer Chris Robinson on Wild 90s Stories & "She Talks to Angels

#590 - Black Crowes Lead Singer Chris Robinson on Wild 90s Stories & "She Talks to Angels

Chris Robinson sits down with Bobby to talk about the early rise of The Black Crowes, the momentum that turned them into one of the biggest rock bands of their era, and what that whole ride felt like ...

27 Mar 1h 7min

#589 - Bobby & Eddie Vote on the 2026 Rock & Roll Hall of Fame!

#589 - Bobby & Eddie Vote on the 2026 Rock & Roll Hall of Fame!

Bobby breaks down his Rock and Roll Hall of Fame ballot and goes nominee by nominee to decide who’s getting his vote and who’s getting cut. Along the way, he and Eddie debate artists like Mariah Carey...

26 Mar 31min

#588 - Avery Anna on Viral Success, Hate Comments & Rules of The Tour Bus

#588 - Avery Anna on Viral Success, Hate Comments & Rules of The Tour Bus

Rising country music singer-songwriter Avery Anna sits down with Bobby to talk about the moment viral success changed everything, why the hate comments hit harder than people realize, and how she lear...

24 Mar 55min

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