Career
Callahan started out as a highly experimental artist, using substandard instruments and recording equipment. His early songs often nearly lacked melodic structure and were clumsily played on poorly tuned guitars (possibly influenced by Jandek, whom Callahan admired), resulting in the dissonant sounds on his self-released cassettes and debut album Sewn to the Sky. Much of his early output was instrumental, a stark contrast to the lyrical focus of his later work. Apparently, he used lo-fi techniques not primarily because of an aesthetic preference but because he didn't have any other possibility to make music. Once he signed a contract with Drag City, he also started to use recording studios and a greater variety of instruments for his records.
From 1993 to 2000, Callahan's recordings grew more and more "professional" sounding, with more instruments, and a higher sound quality. In this period he recorded two albums with the influential producer Jim O'Rourke and Tortoise's John McEntire, and collaborated with Neil Hagerty. Callahan also worked closely with his then-girlfriend Cynthia Dall in his early career, and they contributed vocals to each other's albums. After 2000's Dongs of Sevotion, Callahan began moving back to a slightly simpler instrumentation and recording style, while retaining the more consistent songwriting style he had developed over the years. This shift is apparent in albums such as Rain on Lens, Supper, and A River Ain't Too Much to Love.
Smog's songs are often based on simple, repetitive structures, consisting of a simple chord progression repeated for the duration of the entire song. His singing is characterized by his baritone voice and unemotional style of delivery. Melodically and lyrically he tends to eschew the verse-chorus approach favoured by many contemporary songwriters, preferring instead a more free-form approach relying less on melodic and lyrical repetition. Themes in Callahan's lyrics include relationships, moving, horses, teenagers, bodies of water, and more recently, politics. On the subject of voice in his albums, Callahan has said, "It’s usually one character per record. So, the character appears in all or most of the songs on one record and then is gone. Though it makes me feel weird to talk about. Because I don’t really think in clear terms of characters. My albums as a whole could be seen as one character with many voices." His generally dispassionate delivery of lyrics and dark irony often obfuscate complex emotional and lyrical twists and turns. Critics have generally characterized his music as depressing and intensely introverted, with one critic describing it as "a peep-show view into an insular world of alienation."
Cat Power (Chan Marshall) recorded Callahan's song "Bathysphere" on her 1996 album What Would the Community Think and also covered another Callahan song, "Red Apples", on her Covers Record, released in 2000.
In 2007, Callahan released Woke on a Whaleheart, his first solo album released under his own name. Sometimes I Wish We Were an Eagle followed in April, 2009. Both recordings were released through Drag City, worldwide. In 2009, Callahan contributed cover songs on four separate tribute albums to Judee Sill, Kath Bloom, Chris Knox, and Merge Records. His most recent album, Apocalypse, was released in April 2011 to favorable reviews. Critic Sasha Frere-Jones called it "my favorite of Callahan’s albums, not because it has better songs—those are scattered among at least five others — but because it does exactly what he wants it to do: it conveys an album’s coherence."
It was announced in January 2012 that a tour film chronicling Callahan's 2011 Apocalypse tour would be released later that year.
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