About halfway through Erin Osmon’s recent biography, Jason Molina: Riding With The Ghost, there’s a candid moment where Molina’s band Songs: Ohia is performing at the 1998 BAM festival in Barcelona, along with fellow rising acts Belle and Sebastian, the Magnetic Fields and Will Oldham. Molina is hanging out backstage after his set when he hears a festival promoter remark, “Songs: Ohia is good, but it will never be as big as these other bands because Jason doesn’t have a good story.” If Molina will be remembered, five years since his tragic death, as a man without a story, it might stem from his disinterest in ever becoming one. Molina lived a life in defiance of the kind of legend-making that fans and critics often impose onto songwriters like him. He lived unafraid to be the messy contradiction he was: a man who wrote brutally confessional songs and worshipped authenticity, yet embraced his silliness and told stories so riddled with half-truths and exaggerations that even his closest friends didn’t know when to take him seriously. A man who stood only 5-feet-6-inches, but had a tenor voice that could split your bones, a howl that shot out of him like a phantom. Molina was a man who sang about precisely what mattered most to him, about loving without fear, about riding shotgun with one’s personal demons, until ultimately, he was claimed by them.

Songs: Ohia (The Black Album) (1997) Molina released his debut album under the Songs: Ohia moniker while he was completing his undergrad at Oberlin College. The self-titled record, which fans now refer to as The Black Album, was recorded on an 8-track cassette player in the house of a college friend, much of it in the bathroom. The 13 songs consist entirely of first takes (an approach Molina would apply to all of his records and be forced to fight for). The album remains a testament to the then 23-year-old’s preternatural talent and clarity of vision. Molina wails lyrics redolent of his childhood Civil War obsession, seething with heartbreak and loneliness, ignoring any sort of rhyme scheme or conventional song structure. It’s remarkable how complete instrumentation on The Black Album seems, considering there’s little more happening than the sparkling twang of Molina’s tenor guitar/Fender Champ combo and the tentative drumming of Molina’s high school friend Todd Jacops. The album sold through its modest 200-copy first run, garnering positive reviews and putting Molina’s label, the brand new Indiana-based Secretly Canadian, on the map.

Axxess & Ace (1999) After graduating from Oberlin, Molina moved in with Secretly Canadian label heads Chris and Ben Swanson to continue to release music under the Songs: Ohia moniker. The Helca & Griper EP and sophomore album Impala, while no major leaps in terms of songwriting or production quality, allowed Molina to continue to tour the U.S. and gain confidence playing in front of audiences. Molina’s third full-length record, Axxess & Ace, is a different story. The album marks his first collection of songs written outside of his time at Oberlin; less heartsick art history major, more road-weathered journeyman. Molina had begun his relationship with Darcie Schoenman, the woman he would love until his last days. The songs on Axxess & Ace reflect the initial awe he saw her with, a cornerstone in Molina’s songs that would shift and evolve over their challenging relationship, but never vanish.

The Lioness (2000) Riding the positive reception of Axxess & Ace, Songs: Ohia toured Europe and made friends with Scottish band Arab Strap, whose home studio Chem 19 was available for an impromptu recording session. The group took the opportunity to capture a the songs that would comprise The Lioness, a record about the complexities that had emerged in his relationship with Schoenman. The finished product is another quantum leap for the young songwriter, showcasing Molina’s voice at its most in-command, song arrangements at their fullest and lyrics at their most nuanced. Title track “The Lioness,” a song about the emotional risk involved in letting oneself be loved, became an instant favorite that, much to fans’ dismay, Molina found too emotionally taxing to perform.

Didn’t It Rain (2002) After moving to Chicago with Schoenman, Molina transformed Songs: Ohia from a solo moniker into a rock band. Touring songs from The Lioness with this new group of gifted Chicago players, Molina developed a taste for dynamic, sprawling rock arrangements. He was also listening to Gospel and Blues music around this time, with a particular affinity for the Muscle Shoals sound of 1960s Alabama. All of this informed the record he was writing, Didn’t It Rain. Molina booked a converted factory in Philadelphia called Soundgun Studios and brought in musicians who had never worked together before, who recorded their parts after only minutes of practice. This spontaneous, lightning-in-a-bottle energy is perhaps best captured during the live vocal take for “Didn’t It Rain,” where you can hear Molina whisper to singer Jennie Benford, “Let’s bring it back, we can sing one more time.” Equal parts haunting and soulful, with lyrics steeped in working-class struggle, desolate landscapes, and the singer’s closeted battle with depression, the release of Didn’t It Rain would be a game-changer for Molina, who’d go from a songwriter frustrated with comparison to a singular voice in American music.

The Magnolia Electric Co. (2003) When Molina invited his Songs: Ohia bandmates to join him at Steve Albini’s legendary studio Electrical Audio in Chicago, all he told them was that they’d be recording a rock record. The session that unfolded marked the first time all of Molina’s bandmates were in the studio together, a charmed occasion that resulted in what most consider to be the songwriter’s crowning achievement. The songs on The Magnolia Electric Co. are a not only a near-perfect distillation of Molina’s strengths and calling-cards as a musician, but also a roadmap for the music he’d go on to make. The record is brimming with stand-out vocal performances from Benford, Scout Niblett and Lawrence Peters, as well as glimmering lap steel from Mike Brenner. Lyrically, Molina is at his best, delivering couplets that are by turns razor-sharp and heart-wrenching: “Everything you hated me for / Honey, there was so much more,” he sings on “Just Be Simple,” and then later, on “Hold On, Magnolia”: “You might be holding the last light I see / Before the dark finally gets a hold of me.” It was almost immediately after its release that The Magnolia Electric Co. became a universally adored record that maintains an almost mythical adoration from fans and musicians to this day.

Let Me Go, Let Me Go, Let Me Go (2006) By the time Jason Molina released Let Me Go, he was nearly a decade removed from that Oberlin student flailing his voice against sparse, home-spun arrangements, though he never stopped performing that way. Throughout all of his time playing and recording with Songs: Ohia and Magnolia Electric Co., Molina was liable to take off for the occasional string of solo shows (often without informing his bandmates), as though the time away from the group was something fundamental to his being. If Let Me Go’s title doesn’t do enough to support this notion, the ghostly introspection of it will. In his lyrics, Molina conjures the supernatural, searching for answers in the stars and in an ocean that doesn’t wave back. In some ways it’s classic Molina, but a closer listen reveals a singer who’s moved past the heady outsider poet, intellectualizing the strife of the common man, and into the place of someone in desperate need of answers for the impossible questions he’s asking.