1 hour 16 minutes | Thursday, May 28, 2026
Vanessa Carlton sits down with Bobby to look back on the moments that shaped her career, from the lasting impact of “A Thousand Miles” to why she still chooses to open her concerts with it. She also shares what it was like performing with Drake, rates her memorable first pitch performance, and tells the story of how a man in a castle helped launch her music career. Vanessa also talks about life on the road, why she tours with a fan, and how her relationship with her biggest song has evolved over the years. Watch The BobbyCast on Netflix! Follow on Instagram: @TheBobbyCast Follow on TikTok: @TheBobbyCastSee omnystudio.com/listener for privacy information.