Wed., Jan. 16, Jennifer O’Connor

Naked Lounge Downtown, 8:30 p.m., $5

On the surface, Brooklyn-based singer-songwriter Jennifer O'Connor seems like one of those overly earnest coffee-shop crooners—all serious feelings and joyless melodies. In reality, however, the 39-year-old O'Connor has mastered the art of insightful, biting observation. Her lyrics cover intense autobiographical ground (a terminally ill sister, a cheating girlfriend, et al.) without ever turning into cringeworthy TMI sulkfests—quite the feat. Previously signed with Matador Records, O'Connor was dropped after her 2008 record Here With Me enjoyed critical but not popular success. These days, she runs her own label, Kiam Records, through which she released her latest album, I Want What You Want. 111 H Street,