Bobby Bones Presents: The BobbyCast

Bobby, Eddie and Brandon draft the best country songs that successfully crossed into the pop world. From Dolly Parton and Johnny Cash to Taylor Swift, Shania Twain and Chris Stapleton, each of them builds a five-song lineup filled with massive hits that reached far beyond country radio. Along the way, Bobby shares a story from his early days in Nashville, the guys challenge a few questionable picks, and the debate gets competitive as they make their case for the strongest draft.
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Singer/Songwriter Stella Lefty sits down with Bobby to talk about the unfinished TikTok that changed everything when “Boston” unexpectedly took off. She shares how stage fright kept her from performing, why she hid her musical ambitions and the bold DM that led to her first Nashville writing session. Stella also opens up about moving from Chicago to New Orleans and Los Angeles, becoming an artist after writing for others and how she met her boyfriend, Vincent Mason.
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On this episode of Current Stuff, Bobby shares the shocking amount he just paid for new tires, explains why he was once turned away by a tax preparer for making too much money, and breaks down exactly how much of his paycheck goes to agents, managers, and taxes. Bobby also reveals the bucket list item he's been trying to make happen for years. Bobby and Eddie then debate whether fans should get refunds when singers perform while sick after recent concert cancellations and shortened shows. They also talk about a list of the 10 most likeable celebrities and debate whether celebs like Tom Hanks and Steve Carell are really as nice as they seem??
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Entrepreneur and social media expert Gary Vaynerchuk sits down with Bobby to break down what it actually takes to become a successful creator in today’s crowded online world. He explains why quantity, persistence and a willingness to be judged can matter just as much as talent. Gary also shares his outlook on the future of AI, how everyday people can begin using it to their advantage and why resisting new technology could leave them behind. Plus, they discuss America’s political division, the public’s growing exhaustion with constant outrage, the importance of personal accountability and why Gary remains optimistic that respect and civility are beginning to return.
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Bobby counts down his top 10 Alan Jackson songs and shares the personal stories, memories and fun facts behind each pick. He talks about growing up listening to Alan, the guitar Alan gave him with the message “keep it country,” and their memorable first meeting. Along the way, Bobby breaks down classics like “Chattahoochee,” “Don’t Rock the Jukebox” and “Remember When,” reveals which songs surprised him by being covers, and explains why Alan Jackson remains one of country music’s greatest songwriters.

Watch The BobbyCast on Netflix!
Follow on Instagram: @TheBobbyCast
Follow on TikTok: @TheBobbyCast
See omnystudio.com/listener for privacy information.