The Barenaked Ladies have a funny streak 100 miles long, but keyboardist and multi-instrumentalist Kevin Hearn’s is different—more whimsical, less yuk-yuk dopey—than those of Ladies frontman Ed Robertson and former singer Steven Page. It comes as no surprise, then, that Hearn’s Thin Buckle project, which while you weren’t paying attention has now been around for almost a decade, is an appealing showcase for his solo songs and pop sensibility. He has a lighter, mellower touch than other pop tunesmiths like Ben Folds, but his songs have almost surprising depth at times. They’re light, and they don’t force; they don’t come to you. You go to them with a nugget of curiosity, and then you realize they’re not as light as you think.

Havana Winter continues that streak and is Hearn’s best solo album to date. He’s joined here by drummer Great Bob Scott and bassist Chris Gartner—both former bandmates from the Look People, one of Toronto-based Hearn’s many regional side projects—along with guitarist Brian Macmillan and guest guitarist Mike Rathke, known for his production work and as a Lou Reed sideman. Together, they offer plenty of world-weary-but-still-smilin’ fare like “Coma” and “Reeling”, which cover distraction and loss and “On the Runway”, which suggests either adventure or regret but probably isn’t about either.

Not all of it is strong: “In the Shade” and “Huntsville, CA” are both throwaways, harmless as they are, and Hearn has a tendency to mistake vapid for ethereal with some of the arrangements. But the fun part is listening to Hearn escape pigeonholes. “Coma” seems like it’s going to wrap up by petering out, and then it burns to a close with an angry, stabbing guitar solo that changes much of the song’s tone. “Luna,” which contains the line, “If you were lost at sea / What kind of a lighthouse would I be?” suggests a Barenaked Ladies cut, but it’s about the pain of a departed loved one, more gauzy than dreamy. It’s these unique touches that find Thin Buckle approaching Broken Social Scene territory—fitting, as Hearn’s worked with plenty of the BSS ranks, too—and loading these quirky songs with unexpected resonance.