If people’s ideas about art often are formed early in life, before they even know what’s happening, then Bill Callahan can be glad his father had good taste. “My dad used to listen to Willie Nelson when he ironed his shirts,” the singer-songwriter who fronts the indie-rock band Smog, said. “When I was a kid, my bedroom was in the basement, and he set up the ironing board down there, and on Sunday nights he would iron all his work shirts for the week. You know how some people only have one tape? He had this one tape of Willie Nelson he would play over and over.”

Aspects of that early exposure to the redheaded stranger may or may not be evident in the eight albums Mr. Callahan has released since 1990. That includes his new one, “Woke on a Whaleheart” (Drag City) — in stores today — which is the first recording he’s put out under his own name. But there is a certain approach to singing that fits the performer quite naturally. His unfussy baritone would have served him well in another generation, when Mr. Callahan might have held down the low end in a gospel quartet or string band rather than creating somber soundscapes with post-rock studio wizards such as Jim O’Rourke and John McEntire (of Chicago’s Tortoise).

“I found my own way into country music,” Mr. Callahan said, munching on a Caesar’s salad in a nondescript diner we ducked into one recent evening near Gramercy Park. The singer, a Maryland native who now lives in Austin, Texas, was in town to promote “Whaleheart,” which reunites him with sometime-collaborator Neil Hagerty, the guitarist for the lo-fi 1990s rock duo Royal Trux. Spoiling Mr. Callahan’s image as a depressive introvert, the album resonates with a quiet, quirky joy, dressed up in Mr. Hagerty’s imaginative arrangements, which seem to echo from an old vinyl jukebox suspended between pop eras. The album sounds like countrypolitan grunge, and serves as a reminder of a time when country music was a refuge and a platform for surreal and poetic sensibilities, a perversely individualistic form that could also play a subtle hand. You can get that in the skewed humor of a title like “A Man Needs a Woman or a Man To Be a Man,” a quality accented by Mr. Callahan’s deadpan delivery.

“I couldn’t really find my way into singing until I got into country — like the Stanley Brothers,” he said, referring to the bluegrass legends. “Ralph Stanley. I like the way they tell stories that can be joyful or tragic, but they sing them in the same voice. There’s not this overblown emotional delivery. It’s kind of hypnotic.”

At its best, “Whaleheart” achieves the same effect. Tracks like “Diamond Dancer” evoke a dreamy swirl and an air of emotional contentment. “The theme for the record is people realizing good things or important things,” Mr. Callahan said. Much as his singing voice, he speaks in a soft, deliberate tone, and rarely uses more words than he has to. He often smiles at the conclusion of a thought, as if there’s something else he could express but would rather keep in reserve, for his own amusement. “They are positive songs.”

The upbeat feeling might owe something to Mr. Callahan’s relationship with the virtuoso harpist and songwriter Joanna Newsom, who appeared on Smog’s 2005 disc, “A River Ain’t Too Much To Love,” and has joined him onstage to play piano. But there’s also the creative pleasure of turning over the production to Mr. Hagerty. “He had so much enthusiasm for the music, he seemed like a safe bet,” Mr. Callahan said. “He wanted to create music that didn’t draw on a particular time or place. The songs sound like they could have been made at any time in the last 30 years.”

There’s also the matter of Mr. Callahan’s relocation to Austin, that slacker oasis in the middle of Willie Nelson’s beloved Texas hill country, where he recorded “Whaleheart” with a combo of local musicians. “There’s a supportive attitude. Everyone’s in it just for the love of music. They’re not trying to get anything out of you,” he said. “I mean, you can even go down to the bank and say you’re a musician, and they’re fine with that.”