A timid teen is subjected to the romantic ministrations of a brazenly skilled young paramour and turns into a track star. A daily bus commuter slowly descends into a regular argument with an ornery old cuss who thinks the problems of today are all the fault of young people and glam rock. A street kid caught up in rough trade stops to wonder if that’s all there is. A spiritual seeker goes to a priest for guidance, and receiving only useless dogma in return, decides to worship television instead.

These are just a few of the faces that show up in 1996’s marvelous second LP by Belle and Sebastian. At once rousing and mournful and positively buzzing with the erotic friction of sin and salvation, If You’re Feeling Sinister manifests an unarranged meeting of disparate outlaws—the lineal descendants of Bowie’s pretty things, the Modern Lovers’ disaffected suburban bohemians, and Paul Westerberg’s invisible strivers. In 10 songs, singer-songwriter Stuart Murdoch constructs his shadow kingdom piece by piece, an emotional voting block of consummate misfits: the poor, the ugly, the queer, the socially maladroit, those for whom the compensations of contemporary life feel insufficient relative to its nonstop petty humiliations. A shimmering, comic-tragic signal flair for those who feel abandoned and a destination for those with nowhere to go.

Five months earlier, the band made waves with their frequently brilliant and charmingly homespun debut Tigermilk, which helped to establish the rough contours of Murdoch’s preoccupations: dancing, dreaming, shy boys, sly girls, high-school hierarchies, the plight of the unrequited, and the sundry pilgrimages of the heart and mind. It was by any measure a strong statement of purpose, buoyant and scrappy and replete with promise. If You’re Feeling Sinister was something else entirely—a streamlined juggernaut whose layered character studies were filled with exquisite literary and musical detail. Such is the power of Murdoch’s storytelling that it can be easy to lose sight of the idiosyncratic brilliance of If You’re Feeling Sinister’s marvelously calibrated hybrid of Fairport Convention-adjacent British folk and late-period Velvet Underground surliness, a hiding-in-plain-sight aesthetic pairing that provides a rich sonic tapestry for Murdoch to embroider his outsider’s guide to the galaxy. The pastoral feel of the music, and Murdoch’s soft, tremulous tenor conjures Nick Drake, but the content of the songs hews closer to the urban fever dreams of Martin Amis, whose 1995 novel The Information traces similar lines of fading-empire disenfranchisement.

Stuart Murdoch is a character in his own songs, largely a comedic one, and he tends to exist at a remove. A lapsed-but-simmering Presbyterian zealot, he’s always calling balls and strikes on everyone’s perversions but his own. He’s a strange anthropologist of the underground, a little overstimulated, thrilling to the milieu without quite jumping in—a beguiled wariness regarding the weird edges of town he shares with his Canadian contemporary Dan Bejar. He asks peculiar questions. “Have you and her been taking pictures of your obsessions?” he gently interrogates a young woman in a detective’s cadence on the spectacular album opener “The Stars of Track and Field.” He’d like to know, because he has definitely been taking pictures of his. The rollicking, seasick “Seeing Other People” is a piano-driven paean to bewildering bi-curious sexual confusion, resolving around a killer punchline: “You’re going to have to go with girls/You’d be better off/At least they know where to put it.”

In “Me and the Major,” a scintillating blues harp soundtracks a pointless circular disagreement with an officious Boomer as to whether the Queen’s army is where one goes to learn to be a man. Where does one go to learn to be a man? Or to learn anything, for that matter? The sins of the father are cheerfully sloughed off on the son. “All the others took drugs,” Murdoch sings of the preceding generations, turned censorious in their dotage. “They’re taking it out on us.” They still are to this day.

The album’s title track and centerpiece is a five-minute-twenty-second series of perfect, steel-guitar abetted snapshots of doomed characters adrift in spiritual crisis, seeking nourishment from religious institutions that traffic largely in corrupt predation and outdated ritual. All around there is the pre-Brexit feeling of Potemkin institutions of church and state, lost somewhere in the deafening reverberations of history, insufficient to meet the physical and psychic needs of a younger generation:

“Hillary went to the Catholic church because she wanted information
The vicar or whatever took her to one side and gave her confirmation
St. Theresa’s calling her
The church up on the hill is looking lovely
But it didn’t interest
The only thing she wants to know
Is how and why and when and where to go
How and why and when and where to follow”

At times, critics have interpreted Murdoch’s songs as compositionally simple—a spare edifice around which to hang his stories and aphorisms, with backing crew providing their baroque but down-home orchestral support. I suspect this has something to do with their nominal relationship to the “twee” movement, a specific kind of aggressive guilelessness that ran through Scotland’s Postcard Records and Olympia, Washington’s K label. Those kinds of records—Talulah Gosh and Beat Happening—tended to the lo-fi and amateurish as a point of pride. No doubt, some of that filtered through to Murdoch, but it did not emerge in simplicity of arrangement. Indeed, the thorniest of Murdoch’s tunes here—the galvanizing keep-yourself-safe “Like Dylan in the Movies” or the passive-aggressive devotional “Mayfly”—are as delightfully and compositionally difficult as your average Todd Rundgren song.

In his late 20s at the time, Murdoch was commencing a staggering hot streak that would last roughly a decade. A couple Belle and Sebastian LPs during this stretch would suffer from the decision to delegate several songs to sundry bandmates, particularly 2000’s uneven Fold Your Hands Child, You Walk Like a Peasant, which shines on Murdoch’s material and is considerably diminished by lesser contributions by Stevie Jackson, Isobel Campbell, and Sarah Martin. Who knows the reasons for this choice—band dynamics are a psychedelic kaleidoscope of competing imperatives—but whatever the case, by 2003’s Dear Catastrophe Waitress, Murdoch had been largely restored to creative primacy, on both that record and The Life Pursuit. Such a decade-long streak is historically unusual. Sly Stone from 1967 to 1976. Joni Mitchell from 1968 to 1977. Dylan, a couple of different times. Anyway, If You’re Feeling Sinister launched the band into a rarified air from which it would not soon descend. Thirty years later, the group has evolved into the very sort of communal institution and devoted cult that Murdoch dared dream into reality.

After all of the bone-deep hooks, ribald jokes, and meticulous world-building, If You’re Feeling Sinister ends on the sort of galvanizing grace note that used to come so easily to Morrissey, before his hardwired paranoia finally overtook his vaulting compassion. With its lilting, sing-song progression and vaguely goofy brass interlude, “Judy and the Dream of Horses” is a sweet-natured mash note to a bookish teenage rebel, the sort who is equally interested in S&M and Bible studies, who maybe wants to know how and why and when and where to follow. Don’t follow, Murdoch seems to tell her: Lead.

Additional research by Deirdre McCabe Nolan.