Sheryl Crow on “Crazy” (special Willie’s birt...

With the holiday season in full effect, we’re reaching back to OBW’s earliest days to re-up this Nov 2020 episode with Lumineer Wesley Schultz on Willie’s initial contribution to the holiday canon, “Pretty Paper.” Wes was a little kid growing up in the New Jersey suburbs when he ...  Show more

In a special, icon-on-icon birthday tribute, 13-time Grammy winner and longtime Willie friend, fan, and collaborator Bonnie Raitt talks about their sublime 1993 duet, “Getting Over You.” It was a cornerstone of one of the most important albums of Willie’s career, Across the Borde ...  Show more

The Skye Boat Song brings back a wealth of childhood memories for many.The words "Speed Bonnie Boat Like a Bird on the Wing" tell the story of Bonnie Prince Charlie’s escape to the Isle of Skye - dressed as a maid - after defeat at the battle of Culloden.Originally written by Sir ...  Show more

"Strumming my pain with his fingers... Singing my life with his words..."Killing Me Softly with His Song is a song about the pleasure and embarrassment of being seen. The feeling that someone has reached into your deepest, most private feelings, and laid them bare. It's a song ab ...  Show more

Bobby talks to his friend Keith Urban about his new song Wild Hearts, how he re-wrote the verses and his favorite country song and lyric of all-time. Raymundo recently saw comedian John Crist at the mall and claims he was snubbed by him. So we talk to Jon and get his side of the ...  Show more

Bobby talks about why he got in trouble at Amy’s daughter’s birthday party over the weekend. Was he in the wrong?? We talk to Alan Jackson about releasing his first new music in 6 years, his hits from the 90’s and the song his wife thought was dumb and went on to be a big ol’ hit ...  Show more