Living Legend: Bobby Bare Sits In For Rare Interview On Dillon Weldon's 'Drifting Cowboy' Podcast

By Paul Howard on February 9, 2026

I don't know when or where I first heard Bobby Bare's music, but once I got my hands on his 1973 album Lullabys, Legends, and Lies, he quickly became a favorite.

"Gather 'round fellas / I'll tell ya some tales / About murder and blueberry pies," he sings to open the record. If that line alone doesn't draw you in, I don't know what will. It sets the stage for an epic and very original country album.

His wit, phrasing, and vocal delivery is unparalleled, and hit songs like "The Winner," "Marie Laveau," "She's My Ever Lovin' Machine" and many others just hit different. And thankfully, he's one of the few iconic country songwriters of yore still kickin' at the ripe age of 90.

Bare's effect on the country music has had an everlasting impact on generations of musicians and songwriters all over. The songwriting legend has naturally winded down his music career and public appearances over the past decade, and has only done a handful of interviews in that time.

However, he was recently approached to do Dillon Weldon's 'Drifting Cowboy Podcast,' which has gotten comments from viewers comparing his style to that of Bare's on his '80s television show Bobby Bare and Friends. Bare agreed to sit down for a rare long-form interview at his home outside of Nashville to discuss his career, his impact on the genre, and recollect old stories with his friends, many of whom would be on the Mount Rushmore of Country Music. The episode captures iconic moments in country music history in Bare's own words.

"Bobby Bare is one of the most important figures in the history of country music. To be able to sit down with him and discuss his career and contributions to the genre was the absolute privilege of a lifetime," states Dillon Weldon.

Born in Ohio, the Country Music Hall of Famer and Grand Ole Opry member's songs led him to nearly five dozen Top 40 hits from 1962 to 1983. The original "Outlaw" of country music, Bare has been honored with many awards and accolades, multiple GRAMMY nominations and wins and an induction into the Country Music Hall of Fame in 2013.

An architect of the Outlaw Movement, he gained control over his own production and created country's first concept album, A Bird Named Yesterday, in 1967. Throughout his career, Bare championed the works of legendary songwriters like Tom T. Hall, Kris Kristofferson, and Shel Silverstein, whose collaboration with him resulted in the landmark album, Bobby Bare Sings Lullabys, Legends and Lies.

Over six decades, he has released 38 albums and influenced countless artists, including Waylon Jennings and Billy Joe Shaver among others. Bobby Bare's legacy endures as a testament to the power of deeply compelling and creative storytelling in music.