Vance Gilbert was a jazz singer before he decided to adjust his style and hit the Boston singer-songwriter circuit in the early 90s. There he caught the attention of Shawn Colvin, who invited him onto her tour as an opening act; three well-received CDs on the Philo label followed. His latest disc, last year’s One Thru Fourteen (Louisiana Red Hot), showcases his deft classically influenced guitar technique, his facility with pop-folk melodies, and his supple vocal delivery. Both the arrangement and melody of “Son of Someone’s Son” recall Van Morrison’s “Into the Mystic,” but Gilbert adds a jolt of barroom sentimentality; his tenor is velvet soft yet undergirded with a steely certainty, the voice of a man summoning the courage to be painfully honest with himself and the one he’s wronged. “What Good Is That?,” although it skirts preciousness (“I thought we were rockin’ like Chuck Berry’s band”), is redeemed by Gilbert’s singing, which captures a range of complex emotions. Occasionally he misses his mark: his Lady Day drag act on “I’ll Cry Too” comes off as cruel burlesque, and his attempt at street-bitch sassiness on “Juliana Walks” makes you miss RuPaul. “Eliza Jane,” the tale of an interracial romance gone sour, is strong lyrically, but Gilbert’s self-pitying mewl goes for the skin instead of the jugular. Elsewhere, though, Gilbert draws blood: “Why Are We So Cruel?” is a tormented examination of how oppression and violence have ripped apart African-American families: “Will we ever shake our history? / Or will it follow us forever?…/ Are all the bruises so genetic that we / Can’t discard the weapons?…/ Evolution / Hold me hostage / Save my children / From my tongue.” Friday, May 16, 7:30 and 10 PM, Old Town School of Folk Music, 4544 N. Lincoln; 773-728-6000.

Art accompanying story in printed newspaper (not available in this archive): photo/Craig Harris.