Jeff Tweedy is a prolific songwriter and poignant lyricist. So why does writing scare him?

Jeff Tweedy is known to fans as a prolific songwriter and poignant lyricist. So it may come as a surprise that the frontman of the Grammy-winning rock band Wilco has long found the act of writing intimidating.

“I’ve always been really afraid of prose because I wasn’t good in school. I was always underachieving. And part of it was I always felt overwhelmed by how much there is to say,” he says.

Perhaps ironically, that fear is in part what compelled a young Tweedy to start writing music four decades ago.

“Songwriting is condensing things and giving yourself the freedom to omit lots of things, just to try and get the essence of an emotion or the essence of a story to come through,” he says.

But as he gears up to release his third book on Tuesday, Tweedy admits the task of writing no longer daunts him the way it once did. Having already tackled a memoir and a “how to” book on songwriting, Tweedy is now shifting his attention to other musicians and the ways their art has influenced him in “World Within a Song.”

The book is just as much about the circumstances in which Tweedy experienced these eclectic 50 tracks as it is about the songs themselves — the comfort that hearing “Somewhere Over the Rainbow” with his Judy Garland-loving mom brought him as a kid or the ways in which Minutemen’s “History Lesson – Part II” bred his longing to be a rock star.

And while Tweedy, whose unadulterated love for music is still palpable after decades in the industry, recognizes the benefits of the unfettered access to songs that streaming platforms grant, he also laments what is lost when listeners don’t have to “work for it” in their search for music.

“I think that there was something really important about the way my generation and previous generations invested themselves in music. The only way to get it was to pay for it. And once you had made just even that outlay of cash, you made time to find a way into it,” he says. “Now, I think if you don’t like something immediately, there’s 10,000 other songs that you want to go to and find something that’s going to hit you right away.”

To combat that throwaway culture, Tweedy makes a habit of listening to music he’s not into, trying to discern why that is — a practice, he says, that often confuses “the algorithm” used by streaming services to predict people’s tastes.

“I don’t like not liking music. And so a lot of times I visit stuff thinking, ‘I know I’m not a big fan of this, but I want to know what other people are hearing in it,’" he explains. "I think there’s really something interesting about listening to things that you don’t love or don’t think were made for you.”

Although often dubbed an alternative country band, Wilco has bent genres since they first formed 30 years ago, solidifying their reputation for experimentation and resistance to categorization with their seminal 2002 record, “Yankee Hotel Foxtrot” — their bestselling album to date.

“We’ve tried hard to kill genres for ourselves,” Tweedy said of the Chicago-based band’s perspective on their country associations. “It’s an artistic tool, in a way. When somebody is coming at your music with a preconceived notion, then you have some friction to push against. And that’s artistically enticing.”

That genre defiance continues with their 13th studio album, “Cousin,” released in September. The band has spent most of 2023 touring, despite Tweedy’s ongoing battle with osteoarthritis in his hips. The pain is at times debilitating, and even walking short distances proves difficult for the 56-year-old. During a recent show in Los Angeles, though, Tweedy's pain was hardly apparent during a two-hour set.

While the discomfort is at times distracting for him, he says the act of performing does, for brief moments, make him forget.

“Music has an amazing magical power to transport you from pain, emotional and physical, for sure. And I do feel like I go someplace else most of the night,” he said.