#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(706)

#502 - Bobby and His Wife Caitlin on Their European Trip

#502 - Bobby and His Wife Caitlin on Their European Trip

On this episode of the BobbyCast, Bobby and his wife Caitlin talk about their vacation, what celebrity cut them in line, and the best foreign foods! Follow on Instagram: @TheBobbyCast Follow on TikTok...

27 Mar 20251h 7min

#501 - T-Bone Burnett on Turning Jeff Bridges Into a Country Artist, Working With the Counting Crows & Why He Doesn't Like Biopics + Bobby and Eddie Discuss Who Should Get Into This Year's Rock & Roll Hall of Fame 

#501 - T-Bone Burnett on Turning Jeff Bridges Into a Country Artist, Working With the Counting Crows & Why He Doesn't Like Biopics + Bobby and Eddie Discuss Who Should Get Into This Year's Rock & Roll Hall of Fame 

On this week's episode of the BobbyCast, one of the most legendary producers of all-time, T-Bone Burnett, sits down with Bobby. T-Bone talked about turning Jeff Bridges into a country singer, working ...

25 Mar 20251h 11min

#500 - LOCASH on Starting Their Own Label + How Bobby Changed Their Life + Bobby Delivers Some Disappointing News

#500 - LOCASH on Starting Their Own Label + How Bobby Changed Their Life + Bobby Delivers Some Disappointing News

On this episode of the BobbyCast, Bobby sits down with long-time friends and country duo, LoCash. The guys discuss leaving their old record label to start their own and the first time Bobby played the...

18 Mar 20251h 7min

#499 - Luke Bryan on Being a Victim of His Own Success with Songs + The First Time He Got the Call to Be Host on American Idol + The Most Important Song of His Career

#499 - Luke Bryan on Being a Victim of His Own Success with Songs + The First Time He Got the Call to Be Host on American Idol + The Most Important Song of His Career

On this episode of the BobbyCast, Bobby sits down with country music superstar Luke Bryan. Luke talks about how passing on songs that eventually became hits was because he fell victim to his own succe...

11 Mar 20251h 3min

#498 - Bobby’s Favorite TikTok Finds + Songs Entering the Public Domain + The Top 10 Country Music Scandals

#498 - Bobby’s Favorite TikTok Finds + Songs Entering the Public Domain + The Top 10 Country Music Scandals

Bobby and Eddie talk about Taste of Country's list of the Top 10 biggest scandals in country music history. Including when Trace Adkins got shot through the heart by his wife and more! Bobby brings in...

7 Mar 20251h

#497 - Matt Jenkins on  Having 3 No. 1’s in a Year + Tricks to get Over Writer’s Block + Opening for Taylor Swift + Artists Using A.I. In Music + Him and Bobby doing ‘Music Night’ Together

#497 - Matt Jenkins on Having 3 No. 1’s in a Year + Tricks to get Over Writer’s Block + Opening for Taylor Swift + Artists Using A.I. In Music + Him and Bobby doing ‘Music Night’ Together

On this episode of the BobbyCast, Bobby sits down with songwriter, Matt Jenkins. Bobby and Matt talk about doing 'Music Night' together, Matt having 3 No. 1's in a year and how Keith Urban changed his...

4 Mar 20251h 8min

#496 - Ben Williams on Writing Megan Moroney's First Hit + The 2nd Verse Curse + Having a Panic Attack During a Race & Training for an Iron man

#496 - Ben Williams on Writing Megan Moroney's First Hit + The 2nd Verse Curse + Having a Panic Attack During a Race & Training for an Iron man

On this episode of the BobbyCast, Bobby sits down with songwriter Ben Williams. Ben discussed writing Megan Moroney's first hit song "Tennessee Orange" and why he never believed in the '2nd verse curs...

28 Feb 20251h

#495 - Ringo Starr on How He Got His Name, When He Was Introduced to Music, Stories About Playing All Night in Liverpool + Bobby, Eddie & Mike Discuss Most Influential Bands

#495 - Ringo Starr on How He Got His Name, When He Was Introduced to Music, Stories About Playing All Night in Liverpool + Bobby, Eddie & Mike Discuss Most Influential Bands

On this episode of the BobbyCast, Bobby sits down with the legendary Beatles rockstar Ringo Starr! Ringo discussed how he got his name, when he was introduced to music, stories about partying and play...

25 Feb 20251h 2min

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