Mac DeMarco’s gap-toothed grin is the greatest advertisement for his music, personifying both its childlike charm and mischievous essence. Born in 1990, DeMarco (né Vernor Winfield McBriare Smith IV) wasn’t necessarily predestined to become indie rock’s reigning king of chill; he first came up in Vancouver’s late-2000s DIY scene making a spirited, foot-stompin’ racket with garage band Makeout Videotape. But after relocating to Montreal and signing with the Captured Tracks label as a solo artist in 2012, he began to apply the pervading gauzy aesthetics of chillwave to traditional indie guitar-pop tropes, yielding a funhouse-mirrored version of the classic singer-songwriter archetype. Seen from one angle, DeMarco is the consummate slacker, extolling the virtues of morning cigarettes (2012’s “Ode to Viceroy”) and lazily watching the world go by (2014’s “Salad Days”) as he coasts atop a lattice of mercurial guitar jangle that serves as his swimming-pool floatie. But seen from another, he’s a master craftsman and keen observational writer—in the mold of his heroes John Lennon, Harry Nilsson, and Randy Newman—who can deceptively coax profound sentiments from seemingly mundane scenarios, while his increased affinity for tastefully twangy guitar leads posits him as a millennial Mark Knopfler and certified dad-rock revivalist. As his star has risen, DeMarco’s records have only turned more musically simple and emotionally complex, whether he’s pondering his estranged relationship with his father on 2017’s campfire-bossa-nova serenade “My Old Man,” or diving deep into existential malaise via the amiable cowpoke amble of 2019’s “Nobody.” But his increasingly refined approach has not come at the expense of his relatability. As he said to Apple Music, “I think the DIY mentality is an important one, especially at my level, to put across. I’m overweight, I’m going bald, I brush my teeth only once a day, I can’t really play my instrument. But look, I’m enjoying myself. You can do it too.”