mmm...going on from your listing of frank sinatra and ray charles...
sarah vaughan, coleman hawkins, ben webster, peggy lee, nina simone, johnny hartman, john coltrane, etta james, anita o'day, astrud gilberto, stan getz, antonio carlos jobim, dusty springfield, shirley bassey, dinah washington...
and some other favorites of mine:
gotan project, bebel gilberto, m.ward, the flaming lips, cafe tacuba, the shins, everything but the girl, the arcade fire, de-phazz, son house, kevin o'donnell's quality six, eliane elias, portishead, dimitri from paris, astor piazzolla, smoke city, frou frou, royksopp, alicia keys, ted leo + pharmacists, massive attack, death cab for cutie, pink martini, the pharcyde, the roots, jill scott...etc.
andrew bird
andrew bird's bowl of fire