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This story originally appeared in the Jackson Free Press. It was added to the Mississippi Free Press website in 2025.
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Over the course of his career, singer-songwriter Robert Earl Keen has built a fan base that follows him no matter which genre he’s taking on. If his latest album, “Happy Prisoner: The Bluegrass Sessions,” which the Houston native released in February 2015, is any indication, he’s still finding new ground to traverse.

The album topped Billboard’s bluegrass chart upon release and has remained on the list for 45 weeks, currently sitting at No. 13. The Americana Music Association also named “Happy Prisoner” on its annual “Top 100 Albums of the Year.”

“I’m really stepping out with this record,” Keen says in an interview with the Jackson Free Press. “I’m a longtime fan of bluegrass, and one of the great dichotomies of bluegrass is that … the music is always happy, but the lyric is almost always tragic, and I thought, ‘I’ve got to catch this somehow.’ So the way that I came up with (the title) is that my family and I have pajamas that we spend the holidays in and sit around and watch ‘Home Alone 4’ and really terrible Christmas movies. Those pajamas are called ‘happy prisoners,’ and I thought, ‘Wow, that’s it!’”

Given that Keen has released music spanning multiple genres, including folk, Americana, country and country-rock, choosing to tackle bluegrass was about exposing more listeners to the genre as much as it was about his admiration for it.

“There are quite a few people who’ve had no encounter at all with this kind of music, and then they find out that they like it,” he says. “I think if I really did it for any reason, it was for that.”

Video

Robert Earl Keen – “Hot Corn, Cold Corn”