As the name implies, Freakwater is an odd thing. First, there’s the music: Here are Janet Beveridge Bean and Catherine Irwin, two 40-plus women playing country music after growing up in the ’80s, attracted to punk rock and repelled by the day’s take on twang. They’re obsessed with death and the dying, the doomed and the depressed, the damned and the damaged.

For that reason, Freakwater–since 1989, Bean, Irwin and bassist David Gay and now with labelmates Califone serving as the backing band–has hard-won a reputation for being one of the darkest sounds in America. The cover of their latest album–the perversely invasive and deep-cutting Thinking of You–is a gaudy decoupage of gorgeous red roses–on fire. During “Sap,” Irwin turns a sweet dedication into a glowing exhibition of why love can sear the soul, twisting Tom Verlaine’s Venus de Milo image into a deceptively inviting country smile: “The first night I held you in my arms/ Like a straight shot to hell, I fell for your charms.”

But they do it in a way that’s entirely accessible. Sometimes it’s spry, and sometimes it’s slow and steady, but Freakwater’s tunes are always expertly crafted country & western gems, begging sing-alongs just before begging the question, “Wait, what am I singing about?”

“Catherine and I are generally thought of as pretty happy people on the outside, but there may be turmoil on the inside. Profound story songs are generally more captivating, and they require tension, which is often linked with trauma,” says Bean, at home in Chicago, doing laundry and cooking dinner on the eve of Freakwater’s longest tour to date. “The moments where they are upbeat, we just think it’s upbeat until one of us points out that something refers to killing someone.”

Then there are the circumstances, by now legendary in their own right: Freakwater has been threatening to quit the music business for about as long as Irwin and Bean have been a band. Still, Freakwater releases music through Thrill Jockey Records–generally speaking, an indie rock label responsible for Tortoise, The Sea and Cake, Giant Sand and an excellent Jimmy Martin collection–and has been since 1993. But they’ve had other offers. Famously, Steve Earle offered them a semi-major-label deal on his E-Squared imprint, but they refused when label executives wanted Freakwater to work with their studio aces. Onstage in Chicago, Earle proclaimed that Irwin and Bean “can kiss my ass.” Bean laughs.

“For young bands on larger labels, it can be a lot of pressure and I don’t do that well. There are so few demands on Thrill Jockey,” says Bean, busy with life outside of music. “I am in school majoring in African Studies, and I was working full-time but now I’m not. I still play in Eleventh Dream Day, and I play in this other new band, Horse’s Ha [with Jim Elkington of The Zincs, who open]. I have a 14-year-old son.”

But she’s not totally against major labels. Bean isn’t even opposed to all modern country music, which makes sense, since she isn’t aspiring to compete with the handful of country musicians she respects–Lee Ann Womack, Alan Jackson and Allison Moorer. Yes, perhaps the legend is bigger than the band, and–in these days of domestic activity–the stories seem largely incongruous.

“We’re almost all over 40, so we’re not out getting into trouble after shows. I’ve got to get back to the hotel and read some sort of shit for class,” says Bean. “Touring is a misery kind of like childbirth. When it’s happening, you tell yourself to never do such a ridiculous thing again. Then, after a while, you forget about that element.”

So it goes with love, the thing that Freakwater’s characters step into time and again, just to fail in illustrious, poetic, dramatic glory. Of course, the real question is, how autobiographical are Freakwater’s darkest tides?

“It’s all written from personal experience, unfortunately,” Bean says, sighing and laughing. “Maybe some day, someone will hear the song and think it’s written for them.”

Then again, maybe Freakwater is, at heart, sage advice from relative elders, warnings to the kids on what to do in love, or at least the really bad fallout that can come from trying. Maybe it’s a warning for those teetering on amorous malpractice.

Remember, Freakwater is Thinking of You.

Freakwater plays the Local 506 on Wednesday, Nov. 2 at 10 p.m. Tickets are $10. Thinking of You is out now.