Many men in their forties grapple with the anxiety of aging and an ever-changing world by buying a sports car, going on an extended yoga retreat, or getting hair transplant surgery. Joel Plaskett dropped a quadruple album instead. One-upping his triple-LP set Three from 2009, 44 is an even bolder act of musical numerology: 44 largely autobiographical songs, broken up into four 11-song chapters, released on the day before Plaskett’s 45th birthday. To help you make sense of this deluge of tunes, each of the four records is loosely organized around a certain vibe—the welcoming, off-the-cuff roots reveries of the first set, the amplified rock crunch of the second, the more sonically adventurous country-rock spirituals and distorted blues blasts of the third, and the mellow folk comedown of the fourth act. But they’re all united by Plaskett’s signature mix of poignant, scenic storytelling and clever, self-referential wordplay. (As he sings on the rustic serenade “Fall Guy”: “If you’re looking for a quote/To use in your review/How about ‘I could use an editor before I mention you.’”) Where extended-album sets often encourage an experimental sprawl, Plaskett treats each of these songs as a means to further fine-tune his craft and produce timeless songs that can proudly stand alongside the greats, be it the gospel-graced Stones-y ballad “If There’s Another Road” or the rollicking Springsteen-like character study “Tim” (a touching tribute to a departed old friend). But more than simply showcasing a prolific songwriter operating at peak strength, 44 functions as a storehouse of Plaskett’s life experience to date, its most affecting moments steeped in nostalgic teenage memories (the psych-spiked shuffle “The Wizard of Taz”) and tragedy (“Matthew Grimson Songs,” a raw acoustic elegy for an unsung Halifax-scene hero who died in 2018). The albums also feature a “this is your life” procession of guests that the former Thrush Hermit frontman crossed paths with throughout his career, spanning Nova Scotian peers like Sloan’s Chris Murphy and indie-rock heroes like Dave Shouse of The Grifters (whose greasy fingerprints are all over wobbly rockers like “Spray Tan”). True to that communal spirit, Plaskett corrals several of his East Coast musician pals for the closing “A Benefit 4 Dreamland,” less a grand finale than a loose kitchen-party sing-along reinforcing the fact that, for all its grand designs, 44’s most salient qualities are its humble charm and homespun intimacy.