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Jamaican crooner Freddie McGregor may be fortysomething now, but he’s not ready to sit back and rehash his greatest hits on the oldies circuit. While this prolific artist does have a recent best-of compilation, Masterpiece, featuring his ’80s and ’90s catalog, he also has a new effort put out by VP Records, best known for its dancehall releases, and an early ’97 collaboration on Mesa Reggae. Whether using a live band or machine-generated beats, singing Rastafarian odes or lovers’-rock pleas, McGregor has managed to stay contemporary over several decades thanks to his smooth-as-silk timbre, clear articulation, and timelessly melodic pop and slowjam choruses. With young dancehaller Nadine Sutherland at 9 p.m. at the Crossroads, 4103 Baltimore Ave., Bladensburg. $25. (301) 927-1056. (Steve Kiviat)