The independence cost him. The initial response to “Heavy Metal” from important people in his life and from his label did not bode well. “I’d never faced that much pushback and I didn’t know how to handle it,” he recalled. “I was really scared.” Friends and confidants told Mr. Winter the album would flop. “I’d sunk so much time into this, I just felt like an idiot,” he said.

It was suggested that he release the songs as an EP, or shelve everything but the poppiest song on the album: the exquisite and sunny “Love Takes Miles.” In the end, he recorded a new final track — the heartfelt, mournful “Can’t Take Anything,” because he agreed that the record should end with “more of a jump shot” than the “7-minute-er” he had originally planned. After that, Mr. Winter dug his heels in and put out the record he wanted to make.

To everyone’s surprise, “Heavy Metal” has been received as a tour de force, the kind of offering that has people making comparisons to Bob Dylan and Tom Waits (see also: Stephen Malkmus, Jeff Mangum, Bill Callahan and the droller side of Lou Reed’s solo work). But it has also turned Mr. Winter into the kind of artist that has fans analyzing every detail of his impressionistic lyrics and telling him his work has kept them from suicide. In other words, “Heavy Metal” has received the kind of response that a record earns when the artist who made it is on their way to a certain kind of highly personal stardom. His debut solo tour is now sold out.

Getting Out of His Own Way

Mr. Winter started writing songs when he was about 10 years old. The first, “I-95,” was about a lonely trucker. “It was just sort of like an A.I., like spitting out sad stories,” he said. A decade or so after he began, his songwriting had advanced, but Mr. Winter still had a sense that he was following established conventions. When he told his Geese bandmates he was going to make a solo album, it was partly because he wanted to see if he could get out from under those strictures.

“I just listened to stuff that made it clear to me that I had been following rules that did not have to be followed,” Mr. Winter said over lunch at Tam O’Shanter, one of the great, old, dark and gnarled Los Angeles steakhouses. He listed Leonard Cohen, Federico García Lorca and William Carlos Williams as influences in opening up his own process. “They all have this feeling of, like, innocent nudity,” he said. “It’s so plain and so terrible — so aching.” He stared at his Caesar salad, pushing it around with his fork, adding, “I don’t know how they do that.”