1950s

Otis Ray Redding, Jr. (September 9, 1941 – December 10, 1967)

"(Sittin’ On) The Dock of the Bay" became the first posthumous
number-one record in 1968 on both the Billboard Hot 100 and
R&B charts.

The Highwaymen Long Island concert in 1990

“Big Girls Don’t Cry” hit number one on the Billboard Hot 100 on
November 17, 1962, and, like their previous hit "Sherry", spent five
weeks in the top position. The song also made it to number one, for
three weeks, on Billboard’s Rhythm and Blues survey.