A toy piano kicks off “Good Call,” the opening track of I Know Why You Cry. The song also features a pretty wicked violin solo. It’s all part of the unpredictable whimsy we’ve come to expect from Guelph, Ontario’s favourite son, Gregory Pepper. But the song also touches on aging, life struggles, and questions of identity, themes that appear throughout the record. I Know Why You Cry is actually a curated selection from Pepper’s mammoth “Song of the Week” exercise from 2017-18, a “long, cheeky, confessional mixtape” says Pepper that produced 52 tracks of sometimes undisciplined, often manic melody. Amid the chaos of delivering a new song each week Pepper also grappled with classic transitional life events like losing a parent, having a baby, and rebuilding a kitchen. Now, almost two years later, Pepper offers up a precisely crafted distillation of the experience. And the results are good. Very good indeed.

The album’s ‘dark’ side opens rather sprightly with “Good Call,” despite a melody and march-like feel that belies its serious themes. “Bottle of Ink” is basic biography. Pepper is also an accomplished graphic artist that uses his bottle of ink to capture things that are ‘funny and sad when life is a drag.’ Then its full on into darkness, with songs exploring worry (“Worrier Spirit”), loss (“Maybe I’ll See You”), identity (“Unsolved Mystery”) and coping (“Bogus Journey”). But darkness Pepper-style is not really a downer at all. The tuba and Monty Norman Bond coda on “Worrier Spirit” cuts the dread down the size pretty effectively. Things do occasionally get somber, as on “Bogus Journey” when Pepper channels Yann Tierson in his Amélie and Goodbye, Lenin! phase. But never for too long. Case in point: the lovely situational sketch drawn out in “Sublime Sun Tattoo” where a shop song query segues into surreal speculation about Enya’s lonely castle and stalkers so obsessed they stab themselves. It takes a certain kind of wonderfully twisted creativity to deliver this stuff.

Flipped over, the album approaches ‘daybreak’ covering themes like pretension, self-examination, parenting, and mortality. Sound like pretty heavy stuff? Yes, but that’s not the Pepper way. He calls out bullshit on “Art Collector” amid squiggle horns, birdsong, car horn shots, and a cloud of uplifting background vocals. Concerns about parenting and the world our kids will inherit are given voice in a trio of songs, a mini-musical of sorts, that vibe Macca’s macabre Maxwell side, with perhaps a bit of 10cc on “Diaper Hill.” On “Bigger Than Jesus” Pepper cuts through his sardonic armor to offer a song that is just lovely in style and sentiment.  But it’s back on “Father’s Day” where ‘he doesn’t want much’ … ‘just to hear the voice of God or whatever’s on the iPod.’ “Coda” reviews the album’s songs in a wonderful sort of ‘end-ature’ medley.

I Know Why You Cry is Gregory Pepper’s most fully realized and mature work, beautifully crafted, alternatively hilarious and touching, evidence of an artist in full control of his muse. And that is saying something given his impressive back catalogue. This record is heading straight for the ‘best of’ lists. My advice? Get on over to bandcamp and help make this guy a star.