Raucous cheering emanated from New York’s City Winery Sunday night. Undeniably deserved, it still seemed funny directed at the melancholy, but beautiful, well-crafted acoustic songs of Mason Jennings. Jennings, based in Minnesota, has quietly made a career of his undulating, idiosyncratic vocals and somber melodies. So it was no surprise he began with “Adrian”—though I was cheesily hoping for the apt, up-tempo homage, “New York City.” Later in his set, Jennings reprised the cover, “Red Sun,” which he performed the previous week at Carnegie Hall’s Neil Young tribute. With a supporting electric guitarist, it was haunting and still.
But it wasn’t all gloom. Jennings ripped through a number of older songs (“Butterfly,” “Living in the Moment”) in quick succession, and flashing his wry sense of humor too (“Bullet”, and later “Your New Man.”) He also took a turn at the available grand piano on “Sorry Signs on Cash Machines,” a gorgeous melody that longed for a sturdy beat. By wino-shouting opinion, Jennings played “Lemon Grove Avenue” for his inevitable encore, as well as “Keepin It Real.” After almost an hour and 45 minutes, the crowd clamored for more still. The modest Jennings indulged them—if for no other reason than to quiet the sold-out venue—with a dichotomous Valentines presentation: “Your New Man” and “Ballad for My One True Love.”