William Clarence Eckstine (July 8, 1914 – March 8, 1993) was an American singer of ballads and a bandleader of the swing era. Eckstine's smooth baritone and distinctive vibrato broke down barriers throughout the 1940s, first as leader of the original bop big-band, then as the first romantic black male in popular music. Eckstine's recording of "I Apologize" (MGM Pop Single, 1948) was inducted into the Grammy Hall of Fame Award in 1999.