Gentle-voiced Minneapolis indie-pop troubadour Jeremy Messersmith debuted with the lo-fi Elliott Smithery of The Alcatraz Kid in 2006 and, two years later, released the slicker The Silver City, featuring expert production from Semisonic’s Dan Wilson. It was with 2010’s inventiveThe Reluctant Graveyard, written from the perspective of the dead, that listeners outside of Minnesota began to recognize Messersmith’s talent, and by 2014’s kaleidoscopic Heart Murmur, he would be signed to Glassnote Records, the label home of household names like Mumford & Sons and Childish Gambino. Last April, Messersmith uploaded a songbook called 11 Obscenely Optimistic Folk Songs for Ukulele... to his website and, later in the month, released his actual recordings of the ditties, which function as brief, welcome antidotes to our grim times. This is the first of Messersmith’s four-show January residency at Icehouse. With J.S. Ondara and Rachael Kilgour. With Jillian Rae and Gaelynn Lea (Jan. 10), LOTT and Dosh (Jan. 17), and 4th Curtis and Sarah White (Jan. 24).