20. Bill Callahan – Too Many Birds (2009) Callahan’s first album under his own name, Woke on a Whaleheart, was a surprising – and for some fans alienating – deviation into good cheer, but lugubrious business as usual returned on its follow-up, Sometimes I Wish We Were an Eagle, as evidenced by Too Many Birds. This splendidly stark song mordantly reflects on the impossibility of finding your place in the world. 19. Smog – All Your Women Things (1996) A seven-minute rumination on a lost relationship that fixates on his ex’s underwear, All Your Women Things is tender, regretful, profoundly sad and faintly disturbing (“I made a dolly, a spread-eagle dolly out of your frilly things”). Evidence, five albums into his career, that Callahan had matured into a unique songwriting voice. 18. Bill Callahan – Eid Ma Clack Shaw (2009) Misery and dry humour abound in Eid Ma Clack Shaw, which opens with its author desperate to shake the memory of a former lover and concludes with him dreaming the “perfect song” that “held all the answers”, only to discover the next morning that what he had scribbled down is total gibberish, which he sings anyway. 17. Bill Callahan – The Ballad of the Hulk (2019) This is a classic Callahan moment: you can’t quite imagine anyone else coming up with the central conceit of this lo-fi song, which wryly takes the end-credits image from the Incredible Hulk television show – Bruce Banner walking away, sad and alone – as a metaphor for leaving a troubled past behind. 16. Smog – Cold Blooded Old Times (1999) The song that introduced Smog to the wider world, thanks to its inclusion on the soundtrack of High Fidelity, Cold Blooded Old Times offers a no-holds-barred plunge into Callahan’s worldview at its bleakest: a finely-drawn picture of a marriage collapsing – possibly violently – in full view of the children, to an incongruously rocking backing. 15. Bill Callahan – Drover (2011) Rough-hewn, raw and recorded live in the studio, Apocalypse was steeped in imagery from westerns. You could interpret Drover’s lyrics as anything from a metaphor for a touring musician’s life to a straightforward depiction of a hard-bitten cattleman, but as it clatters and twangs ominously, its power isn’t up for debate. 14. Bill Callahan – Coyotes (2022) Callahan’s aim for 2022’s Reality was to “rouse people … make you feel, lift you up”, something he achieves on Coyote with a drowsy, eyes-half-closed acoustic guitar strum, delicate piano and tumbling drums, plus a lyric that ponders animism, reincarnation and- most importantly- everlasting love. 13. Smog – To Be of Use (1997) It’s typical of Callahan’s sense of humour that he borrows the title of a poem by the feminist writer Marge Piercy for a song about his penis. It’s also typical that he subverts rock’s swaggering approach to this subject: To Be of Use is an entirely abject exploration of impotence. 12. Bill Callahan – Let’s Move to the Country (2020) “Let’s pretend it’s a new song. Please. I have nothing else,” wrote Callahan when he reworked Smog’s 1999 track of the same name two decades on Previously a stark depiction of a collapsing relationship, it was now warm, contented and rather lovely, evidence of an ongoing shift in his emotional temperature. 11. Smog – Let Me See the Colts (2005) For a writer characterised as dark and misanthropic, Callahan does wide-eyed wonder remarkably well. No doubt there is someone on the internet with a complex reading of what Let Me See the Colts means, but the lyric genuinely sounds like it’s just about the unexpected pleasure of looking at young horses sleeping. 10. Bill Callahan – Small Plane (2013) A truly beautiful song, inspired by Callahan’s engagement and move to Texas, which uses co-piloting a light aircraft as a metaphor for domestic contentment and developing control over your own life choices. “Sometimes you sleep when I take us home / That’s when I know I really have a home” is a particularly choice line. 9. Bill Callahan – One Fine Morning (2011) Praised by Nick Cave as “sacred” – a song “I can pull over myself, like a child might pull the bed covers over their head when the blaze of the world becomes too intense” – One Fine Morning is sublime: a spare, elegant chord sequence supporting a lyrical quest for “a country kind of silence”. 8. Bill Callahan – Jim Cain (2009) “I used to be darker, then I got lighter, then I got dark again,” sings Callahan, a neat summary of the shifts in mood over his oeuvre to date. Jim Cain is accordingly very down – the final verse suggests suicidal despair – but the strings feel like shafts of light breaking through the gloom. 7. Smog – I Feel Like the Mother of the World (2005) Callahan’s lyrics understandably draw the bulk of listeners’ attention, but the potent effect of I Feel Like the Mother of the World is derived as much from its sound – a slightly chaotic and relentless take on folk-rock featuring a sparkling dulcimer – as from his voice and its ruminations on God’s existence (“I don’t really care”). 6. Smog – I Break Horses (2002) There’s a Lou Reed-esque tenor to Callahan’s voice on I Break Horses, and you suspect Reed would have been pleased to come up with the song himself: a bleak pen-portrait of an obnoxious misogynist who unrepentantly details his approach to relationships, flecked with dark humour, that is powerful and discomfiting. 5. Smog – Teenage Spaceship (1999) Simplicity is the key to Teenage Spaceship: a three-note riff, a band playing so languidly – and quietly – you fear they are going to stop entirely. It only enhances the power of Teenage Spaceship’s depiction of adolescence in all its arrogance and isolation. 4. Smog – Our Anniversary (2003) Take your pick from the Smog original or the strikingly heavy and noisy 2021 re-recording featuring Bonnie “Prince” Billy, Our Anniversary shines either way. It’s a wickedly funny depiction of the tribulations of a long-term relationship: they are only spending their anniversary together because she has hidden his car keys. 3. Smog – Say Valley Maker (2005) “With the grace of a corpse in a riptide, I let go” is a striking opening line, but the rest of Say Valley Maker lives up to it. The band is a masterclass in restraint, the backing vocals are gorgeous and the lyrics packed with poignant aphorisms: “There is no love where there is no obstacle.” 2. Smog – Dress Sexy at My Funeral (2000) Callahan’s wit is in full flight here – it’s essentially a demand that his (then imaginary) wife enlivens his memorial with stories of “doing it” in unlikely locations – but there’s more to Dress Sexy at My Funeral than laughs. It has a wonderfully unhurried tune and an undercurrent of sadness and regret that keeps poking through the wisecracks. 1. Bill Callahan – Riding for the Feeling (2011) Ask a dozen Bill Callahan fans for their favourite song, and you are likely to get 12 different answers: there isn’t one obvious big hit or classic. Picking his “best”track is down to personal preference, hence Riding for the Feeling. Simply arranged and centred on an exquisitely melancholy vocal melody that is haunted by country and southern soul, it somehow manages to be prosaic – depicting Callahan listening to his own demos – and open to interpretation. Lines that could be about wanting to give up music could just as easily be about grief after a loved one’s death. Deep, sad, clever and haunting: Callahan all over.