Which song became the first posthumous Grammy-winning recording?

“(Sittin’ on) the Dock of the Bay” became the first posthumous Grammy-winning recording when it won two awards for Otis Redding in 1969.

Redding co-wrote and recorded the song with Steve Cropper shortly before Redding died in a plane crash in December 1967. The single was released in January 1968 and became his first number-one hit on both the Billboard Hot 100 and the R&B chart.

At the 1969 Grammy Awards, the recording won Best Male R&B Vocal Performance and Best R&B Song. Its gentle whistling, acoustic guitar, and reflective lyrics marked a change from Redding’s more forceful soul performances.

The song is often called simply “Dock of the Bay,” but its official title begins with “(Sittin’ on).” The parenthetical wording is part of the canonical title.