There aren’t many people who wrote sadder songs than Daniel Johnston did. Or weirder songs. Or funnier ones.

Johnston became famous in that Austin-in-the-early-’90s way that Richard Linklater, the Butthole Surfers, and other fixtures of the city’s transition from sleepy college town to the creative hub for this part of the country did because of those songs. He used to pass them out on cassette tapes he made to customers at the McDonald’s he worked at, and as his local fame grew, he’d sell them at Waterloo Records or the long-departed Sound Exchange, trading artwork out of the similarly-departed comic book store on The Drag. Digging into those tapes to find the gems that could delight you or break your heart took work—the sound quality on many of them is awful, and Johnston’s voice was never conventional—but those who did found huge rewards. The list of fans contains some of the biggest and most important musicians to ever walk the earth—Kurt Cobain, Tom Waits—and the fact that Johnston did all of this as a true outsider only added to his mystique.

That mystique is likely to be amplified now that Johnston is gone. He passed away late on Tuesday night at the age of 58 of natural causes, according to his family, in his home outside of Houston. His life wasn’t always a happy one—he was diagnosed with schizophrenia and bipolar disorder, spent time in psychiatric institutions, and was often in poor physical health. In January, a planned concert in Austin that would have seen Johnston perform with the Flaming Lips, Built To Spill, and more ended up being a tribute performance to the artist instead, who wasn’t able to attend. Johnston’s troubled history was documented in the 2005 film The Devil and Daniel Johnston, which won a directing award at that year’s Sundance Film Festival.

All of that was very much present in Johnston’s saddest songs. His music was often very simple, his vocals childlike. After rising to prominence in the late ’80s and early ’90s, he collaborated with musicians like Sonic Youth guitarist Lee Ranaldo and Half Japanese frontman Jad Fair, who helped create arrangements that complemented the emotion that Johnston expressed through his songs. On 1990’s “Some Things Last A Long Time,” a collaboration with Fair and Galaxie 500 producer Kramer, Johnston’s willingness to lay himself bare combines with the other artists’ talents to create something that’s courageous, and deeply affecting.

Everyone who cares about Johnston’s music probably has a favorite song, and probably a favorite cover, too. Because Johnston often sang unaccompanied, his songs left a lot of room for interpretation—”Devil Town,” a fairy tale about vampires and devils, became a theme song, of sorts, for Friday Night Lights after a rendition by Tony Lucca appeared in several episodes of the show. Tom Waits covered his “King Kong,” a rambling retelling of the story of the film, as a percussive blues jam. Even his most personal and idiosyncratic songs can be especially potent when performed by another artist. “Peek A Boo,” originally recorded as a lo-fi confession in which Johnston sings of mental illness, a painful home life, and how music is both an escape and a trap, takes on a devastating new emotional weight when channeled by Phoebe Bridgers.

Johnston constantly sought ways to express himself. He recorded 17 albums, twelve of them between 1981 and 1991. He was also a prolific visual artist, drawing cartoon animals and monsters (and Captain America, a favorite subject) on notebook paper with markers, before graduating to “outsider artist” status, something that escalated following the documentary’s release. In 2006, the Whitney Biennial hosted an exhibition of his work, and he subsequently exhibited at galleries around the world.

I never met Johnston, but his art touched my life, too. In 2004, shortly after I first moved to Austin, I lived in a studio apartment on 21st Street, a few blocks away from a mural Johnston painted on a record store called Sound Exchange. The piece is Johnston’s best-known work, a simple line-drawing of a frog with a word balloon that says “Hi How Are You.” According to Mike Hall’s 2005 Texas Monthly profile of Johnston, he’d stand on The Drag by the University of Texas and pass out tapes to passers-by, saying, “Hi, how are you? I’m Daniel Johnston, and I’m gonna be famous.”

Sound Exchange closed before I moved into the neighborhood, but one morning, I learned that the construction crew in charge of transforming the former record store into a Baja Fresh franchise was set to demolish the wall that day. I got online and organized some people for an improvised protest, and we got to work trying to think of words that rhymed with “frog” to chant. When we called the owner of the restaurant, he apologized for mistaking the mural for graffiti and explained that it was too far into the process to do anything about it—instead, he offered to carefully cut the mural out of the wall, and I could have it, if I wanted it.

That was never an option for a bunch of reasons (I lived in a studio apartment, for one). The next morning, though, he called me to tell me that he hadn’t been able to sleep. As an art lover—and as someone coming into a new community with a new restaurant, surely—he hated the idea of destroying a piece of art that mattered to people. Instead, he told me he’d been on the phone with his architect, and while it would delay the opening of the restaurant by a couple months, he wanted to save the frog.

I think about that a lot, because it speaks to Johnston’s ability to reach people with his art. For years, I had a cynical read on the situation—that the owner of the restaurant was looking to avoid bad publicity, and instead pivoted to the “businessman saves local landmark” PR strategy—but that’s too dismissive. He may not have looked at the frog mural and said, “That’s how I feel inside all the time,” but he quickly developed an appreciation for Johnston’s art. When I spoke with him again, several years later, the restaurant had long closed, but he’d acquired more pieces of his work for his personal collection—as well as a large acrylic painting that he’d commissioned for the restaurant (along with licensing the frog image for the uniforms). He never did develop a taste for Johnston’s music, but the art spoke to him.

The ways that Johnston found to express himself spoke to a lot of people. His work—in a variety of ways, and in a variety of media—was about loneliness, alienation, and longing, but the way he expressed those feelings connected him to a lot of people, all over the world, who may not have had much else in common with him. For as difficult as Johnston’s life seems to have been at times, that’s a worthy legacy for anyone to leave behind.